History Main / MyGreatestFailure

** In "[[AfterTheEnd the Kingdom]]" AlternateUniverse, Matoro failed to reach Karda Nui and use the Mask of Life in time, causing Mata Nui to die and the entire Matoran Universe (actually [[spoiler:the inside of the gigantic Mata Nui robot]]) to become uninhabitable. He finally redeems himself millennia later by [[spoiler:[[TakingYouWithMe killing Teridax after he absorbs Matoro]]]].

* Lesovikk in Toys/{{Bionicle}} once briefly hesitated in a fight against a group of Zyglak, costing him his entire Toa Team, and driving him into a millennia-spanning HeroicBSOD and WalkingTheEarth for ages.

From a philosophical standpoint, this makes sense — if someone wins all the time, [[TheGoodGuysWin as heroes tend to do]], they would be more defined by their failures than their successes. In Creator/MarvelComics, this is sometimes a consistent psychological flaw (the "Marvel Flaw") which occasionally prevents a hero from succeeding.

From a philosophical standpoint, this makes sense — if someone wins all the time, as most comic book heroes do, they would be more defined by their failures than their successes. In Creator/MarvelComics, this is sometimes a consistent psychological flaw (the "Marvel Flaw") which occasionally prevents a hero from succeeding.

* ''VisualNovel/{{Grisaia No Kajitsu}}'': Amane and Sachi are living with this kind of regret:

* ''WebAnimation/{{RWBY}}'': Jaune Arc is hit hard with that. He blames his own weakness and inability to stop [[StarCrossedLovers Pyrrha]] from fight Cinder as the reason why his partner and best friend dies. Not be able to recognize that Pyrrha was actually in love for him made that worse to Jaune. It takes until Volume 6 to Jaune forgives himself, but he still misses her and mourns her absence. Part of his current armor and weapons are made to honor Pyrrha's memory.

* Agent Carolina from Machinima/RedVsBlue is this in SO many spades over her previous [[CompetitionFreak overly-competitive]] nature to please her disconnected father so long ago, where she had a great many opportunities to drive off her self-destructive path of proving herself to Project Freelancer, with the Project itself destroying the other Freelancers' lives over time during its ruinous slog of development of its AI Fragments during the years of its activity. she definitely feels multiple ripples of this '''BIG time''' after many of her former comrades died, earning the eternal vengeance of an [[PlayingWithFire inferno-obsessed]] [[PyroManiac pyromaniac]] and seemingly forgets a time she accidentally killed a '''very''' dear friend of a Simulation Trooper, thus having him vengefully haunt her later on in the future and giving her a VERY '''[[WaxMuseumMorgue horrific]]''' view of what happened to the other surviving agents leftover from the disbanded Project Freelancer. She especially gives [[spoiler: a past version of herself a '''very scathing''' "talk" involving her aforementioned self-destructive victory-obsessed-self, essentially [[IHatePastMe hating on her past-self a very great deal.]] ]]

[[quoteright:300:[[Franchise/StarWars https://static.tvtropes.org/pmwiki/pub/images/sad_stormtrooper.png]]]]
[[caption-width-right:300:Those ''were'' the droids he was looking for.]]

->''"Watson, if it should ever strike you that I am getting a little over-confident in my powers, or giving less pains to a case than it deserves, kindly whisper 'Norbury' in my ear, and I shall be infinitely obliged to you."''
-->-- '''Literature/SherlockHolmes''', ''The Yellow Face''

!!Examples:

[[folder:Anime & Manga]]
* In the ''Manga/Area88'' manga, Hoover Kippenburg blames himself for the accidental deaths of several pilots during a botched training exercise back in Europe.
* ''Manga/AssassinationClassroom'':
** [[spoiler:Koro-sensei/The God of Death]] has two of them: the first being [[spoiler:never properly acknowledging his pupil's efforts, leading to the pupil betraying him and taking up the title of "God of Death" as his own]], the second being [[spoiler:Aguri Yukimura getting impaled by a shot meant for him while giving him a CooldownHug, leading to the bitter realization that even with all his talent and skill, he can't save a life [[HeelRealization because he devoted all his effort into taking them]]]]. Because of these two failures, [[spoiler:he resolves to spend [[YourDaysAreNumbered his limited life]] teaching Aguri's class in her place]].
** Principal Asano turns out to have his ruthlessness rooted in failure as well. [[spoiler:He used to be a kind-hearted and caring teacher much like Koro-sensei, but then one of his former students committed suicide in high school. He blamed himself for not preparing the boy for life properly, and his current brutal teaching techniques are the result of him trying to emphasize strength of will in his pupils, even if he has to resort to using ThePowerOfHate as a motivator.]]
* In ''Anime/BeastSaga'', even though he carries around a sword, Liogre swears never to use one again after accidentally injuring a little deer girl.
* ''Manga/{{Berserk}}'': not being able to [[spoiler:save Casca from being raped by Femto during the Eclipse]] and later realizing that he made a big mistake by [[spoiler:leaving her for two years to deal with her trauma by herself while he pursued {{revenge}} against Griffith in order to deal with his trauma alone]] was Guts' greatest failure.
* ''Manga/BlackJack'': a dying Dr. Honma contacts Black Jack to confess a shameful secret: [[spoiler:when he first operated on Black Jack, he accidentally left a scalpel inside of him, but refused to believe it until he found the blade encased in a calcium shell during a follow-up operation years later]]. The mistake disgusted him so much that he found himself no longer able to trust his own skill as a surgeon, and retired from practice shortly after.
* ''Manga/{{Bleach}}'': Urahara's [[spoiler:failing to save the Vizards was this]].
* ''Manga/BusoRenkin'': after seven years, Captain Bravo still cannot come to terms with the Alchemist Warrior's greatest - and only - failure [[spoiler:where a school was destroyed and devoured by homunculi, save for one girl: ActionGirl Tokiko]].
* ''Manga/DetectiveConan'': it's revealed that Conan/Shinichi can't forgive himself after [[spoiler:a ''very'' SympatheticMurderer was DrivenToSuicide after being uncovered, despite Conan's pleas for him to live]]. Paraphrased:
-->"A detective who [[spoiler:causes the death of a culprit]] is no better than a murderer!"
** Also, many {{Sympathetic Murderer}}s will blame themselves due to their inaction/inability to do anything for the people [[LoveMakesYouEvil for whose sake they kill for]].
* ''Manga/DragonBall'': Kami was the one who created Demon King Piccolo, the latter being formed from the former's inner evil. As such, Kami believes that he's as responsible for Piccolo's misdeeds as much as Piccolo is;
-->'''Kami:''' I should have given up being a god quite some time ago... after all, it was I who brought the fearsome evil known as Piccolo into this world. What right have I to be a god after this? What right have I to go on living?
** Trunks, from the Android Saga, considers his inability to save the Gohan of his future his greatest failure. This pushed him to finally become a Super Saiyan (in the anime), as well as prompt his return to the past to SetRightWhatOnceWentWrong. It gets worse in ''Anime/DragonBallSuper'' when [[spoiler:Zamasu, a god who hated mortals for their supposed arrogance and the fact that the gods always forgave them, ends up infecting Trunks' timeline, forcing that timeline's Zen-O to destroy it completely, leaving him, Trunks and Future Mai as the only remaining beings from that timeline]].
* ''LightNovel/{{Durarara}}'': everything Shizuo Heiwajima [[IAmAMonster hates about himself]] can be distilled into one incident during his childhood: when he was about ten or eleven, he developed a PrecociousCrush on a woman who looked out for and worried about him due to his constant injuries (unaware that they were the result of [[HeroicRROD overexerting himself]] in [[UnstoppableRage violent, uncontrollable bouts of anger]]). One day, while walking by her store on the way home, he saw her being assaulted by Yakuza thugs. Shizuo tried to help. He screwed up. While this wouldn't be the last time he'd end up hospitalizing someone he was trying to protect (the light novels imply that this sort of thing happened ''constantly''), it's the example that sticks with him the most.
** Meanwhile, [[TheLancer Kida Masaomi]] of the same story struggles throughout most the earlier plot with the fact that [[spoiler: years ago, as the leader of the most fearsome gang in Ikebukoro, he got cold feet right when the time came to dash in and rescue his girlfriend who's been kidnapped, resulting in her being beaten into an inch of her life and left crippled]].
* ''Manga/FairyTail'': Lisanna, Elfman and Mirajane's younger sister, [[spoiler:almost]] died while trying to calm Elfman down when his Take Over magic went awry. Though the exact details of the event are unknown, Elfman and Mirajane's lives were completely changed after the event.
* ''Manga/FullmetalAlchemist'':
** Edward Elric feels terribly guilty for pushing Alphonse to help him use forbidden alchemy to try and resurrect their mother Trisha, leading to the loss of Ed's limbs and Al's human body. It takes ''years'' before Edward gets up the courage to ask if Alphonse blames him for it, but the answer is ultimately no; Alphonse even says that he knew the risks and went along with it.
** The Elric brothers consider their being unable to save [[spoiler:Nina Tucker]] from turned into a chimera or from dying shortly thereafter a massive failure, as well as proof that they are ultimately mere humans.
** Major Armstrong, Colonel Mustang, Riza Hawkeye, and several other veterans of Ishval have deep regret and seek to atone for the massacre.
* ''Manga/FushigiYuugi'': Chichiri has spent years trying to atone for the circumstances leading up to his best friend's death. This inspired him to become the calm, dedicated monk we're first introduced to when the series begins.
* ''Franchise/{{Gundam}}'':
** ''Anime/MobileSuitGundam'': [[spoiler:the death of Lalah Sune]], which haunts Amuro Ray for the rest of his life.
** Heero Yuy from ''[[Anime/MobileSuitGundamWing Gundam Wing]]'', as revealed in TheMovie, [[spoiler:accidentally destroyed a building while bombing a military base, killing (at least) a little girl whom he had befriended the day before]]. This put a face on his victims and made him TheAtoner until his encounters with RebelliousPrincess [[{{Ojou}} Relena]] gave him something to fight for.
** ''[[Anime/MobileSuitGundam00 Gundam 00]]'' has quite a lot of these: there's Sumeragi's guilt over [[spoiler:causing a friendly fire incident that killed her lover]] (accidentally: she was given false intelligence), Smirnov's guilt over (indirectly) [[spoiler:killing his wife]] through following his orders, and Setsuna seems to consider [[spoiler:murdering his own parents in cold blood]] as a child to be his. Then there's that whole incident with Saji and the Katharon base...
** ''Anime/MobileSuitGundamAGE'': Flit's guilt over [[spoiler:being unable to stop Desil from killing Yurin]].
** ''Anime/MobileSuitGundamSEED'': Kira Yamato has two of these. The first time being the failure of saving a shuttle full of fleeing civilians, one of them being a little girl he recently befriended. The second time was when he failed to save [[spoiler:Flay Allster, his first love]].
*** And to a lesser extent, Yzak Joule's failure of losing to Kira Yamato. His face was badly scarred during a battle that was inevitably lost. Though he could have removed the scar with surgery, he chose to keep it until he settled his score with Kira.
*** Athrun also seems to feel this way towards Shinn in the latter half of ''[[Anime/MobileSuitGundamSEEDDestiny Destiny]]'' because he couldn't help him see through Durandal and Rey's manipulations.
* ''Manga/{{Holyland}}'': Masaki's is [[spoiler:begging forgiveness from some thugs when he could have stood up to them and took them down]]. Yuu treats [[spoiler:Shinichi getting attacked]] this way.
* Tomiko from ''Manga/IsKichijojiTheOnlyPlaceToLive'' leaves the family dog indoors on a hot summer day, forgetting the air conditioner was on a timer. By the time she gets back, the poor thing has collapsed from heatstroke and dies shortly after. It haunts her even years later.
* ''Anime/KaleidoStar'': Kalos Eido blamed himself for more than a decade for [[spoiler:asking his old friend Aaron Killian if he ''really'' was up to perform the Fantastic Maneuver, thus (inadvertently) planting a seed of doubt in Aaron's mind that caused him to fail and die; this still haunts Kalos up to this day, thus making him vulnerable to SmugSnake Yuri's manipulations... since Yuri is Aaron's son]].
* ''Manga/KenichiTheMightiestDisciple'': [[spoiler:Hayato Furinji sees his inability to prevent [[BigBad his son]]'s FaceHeelTurn as this]].
* ''Manga/KotouraSan'':
** This is how Manabe thought at the end of episode 3, [[spoiler:after Haruka vanished because she thought [[ItsAllMyFault it's all her fault]] that he was attacked]].
** And more importantly, Haruka causing her own mother Kumiko to hate and abandon her pretty much defines who she is today.
** The Head Priest feels that his inability to help Haruka after Kumiko abandoned her was his greatest failure, and vows to bring them back together someday.
** The final episode reveals that [[spoiler:Kumiko actually [[MyGodWhatHaveIDone considers her abandonment of Haruka as this]], calling herself weak for running away from her daughter's problems instead of helping her]].
* ''Manga/TheLegendOfKoizumi'': UsefulNotes/ThePope turns out to have unknowingly [[spoiler:snuck Hitler out of Germany back in '45]]. He has, for reasons that should be blindingly obvious, regretted it ever since he learned what he had done.
* ''Franchise/LyricalNanoha'':
** In ''Anime/MagicalGirlLyricalNanohaAs'', Admiral Graham blames himself for Admiral Clyde's death, as he was forced to destroy the Hestia with Clyde onboard, at Clyde's insistence, rather than let the Book of Darkness take over the ship and use the [[WaveMotionGun Arc-en-ciel]] on the other ships.
** Vita is haunted by an incident between ''[[Anime/MagicalGirlLyricalNanohaAs A's]]'' and ''[[Anime/MagicalGirlLyricalNanohaStrikers StrikerS]]'' in which, [[http://mangadoom.co/Magical-Girl-Lyrical-Nanoha-StrikerS/2/10/ while the two were on a mission together, Nanoha was taken by surprise, injured and nearly crippled]], partly the result of her having [[HeroicRROD overextended herself]]. Vita then dedicates herself to protecting Nanoha about as much as she is dedicated to protecting Hayate.
--->'''Vita:''' I was with her when we left... I should have noticed before anyone else. That day... that memory... I'll never let it happen again.
** Minor character Vice also has one of these: he used to be a sniper of [[ImprobableAimingSkills quite a bit of skill]], but he now pilots helicopters. Why? Because several years back, his little sister was involved in a hostage situation. He tried to shoot her kidnapper but missed... and [[EyeScream hit her in the eye]]. Though she survived (and doesn't hold him responsible, recognizing it as an accident), he cannot forgive himself and resolved to give up sniping.
** At some time between ''Audioplay/StrikersSoundStageX'' and ''[[Manga/MagicalRecordLyricalNanohaForce Force]]'', Subaru was involved in fighting a fire, but despite her efforts, there were many deaths. She then took a leave of absence to train, resolving to become strong and fast enough to save everyone.
** In the backstory of ''[[Manga/MagicalGirlLyricalNanohaVivid ViVid]]'', Claus G.S. Ingvalt's failure to stop Olivie's sacrifice haunted him so much that it got passed down to his descendants via GeneticMemory.
** In ''Anime/VividStrike'', Fuka considers [[WeUsedToBeFriends the loss of her friendship with Rinne]] to be this. For Rinne, it was [[NeverGotToSayGoodbye her inability to be with her grandfather when he died]] and [[NoHoldsBarredBeatdown what she did in retaliation]] to those responsible for keeping her from being with him.
* In ''Manga/MagicKnightRayearth'', [[spoiler:being unable to save Princess Emeraude]] is considered this for Hikaru, Umi, and Fuu. Mostly because they powered through the entire adventure, thinking it was completely straightforward and never thought twice about questioning their mission. It's so bad that, in the anime, Hikaru accidentally creates her own EvilTwin.
* In ''Manga/MahouSenseiNegima'', Setsuna's FailureKnight nature has its roots in an incident where she tried to save Konoka from drowning, fell in herself, and both were rescued by someone else. As a result, she constantly tries to train harder so it won't happen again. Konoka doesn't hold it against her, as they were both young children when this occurred.
** It happens again later on, with Setsuna developing a major [[HeroicSelfDeprecation inferiority complex]] after [[AttemptedRape nearly being defeated]] by [[PsychoLesbian Tsukuyomi]].
*** Also {{subverted|Trope}} in an awesome way in the same scene; when a very large ball-and-chain comes flying towards them, she [[OffhandBackhand slices it in half and doesn't even notice it...]] because she's beating herself up for getting ''weaker''.
* ''Manga/{{Naruto}}'':
** Not being able to save either Sasuke or Gaara is this to Naruto, especially in the infamous TearJerker where he thinks he is useless for not being able to save either. Thankfully, Gaara gets better, at least in the physical sense. [[spoiler:Sasuke takes until the end of the series, but eventually he comes back too]].
** Jiraiya looks back on his life as a long series of failures, but the one that most stands out is failing to stop Orochimaru's descent into evil.
** Kakashi views most of his life as this: he failed to save Obito and Rin, he couldn't stop Sasuke from betraying Konoha, and he couldn't be Obito's eyes.
*** [[spoiler:With the revelation of Chapter 599, his failure to save Obito and Rin is probably what he considers his absolute ''worst'' failure by far]].
** [[spoiler:Minato blames himself for being unable to recognize Obito as Tobi and preventing the entire plot of ''Naruto'' from happening, even though it wasn't his fault, as stated by Kurama himself. And chances are that even if he had recognized Obito, it wouldn't have changed much -- the Obito he knew was long dead by that point]].
*** [[spoiler:He considers his inability to save Rin and protect Obito from Madara's influence as this]].
** Hiruzen Sarutobi, the Third Hokage, has two (and possibly more, seeing as no one has ever been Hokage longer than him): his inability to stop his student Orochimaru after his fall from grace and descent into insanity and inhumanity, [[spoiler:and the destruction of the Uchiha Clan]].
** The Fourth Kazekage, Rasa, saw Gaara as this, discarding him as a failed experiment. However, when he's revived by the Edo Tensei and sees the great man Gaara has become, he realizes that his ''true'' failure was not being a good father to his youngest son, by robbing him of everything good in his life as a way to test his "worth".
* ''Manga/OnePiece'': A lot of the backstories of characters involve this:
** For Chopper -- not being able to save Dr. Hiriluk.
** For Franky -- failing to save Tom from the World Government.
** For Luffy -- [[spoiler:the defeat that scattered the Straw Hat Pirates at the Sabaody Archipelago]].
** And now [[spoiler:not being able to fully save Ace]] will haunt both Luffy and Jimbei for years to come.
* In the horror manga ''Presents'', Kurumi recalls an incident with a young girl whose parents would give stuffed rabbit toys as a substitute for love. Kurumi takes pity on the girl and, even though she knows better, lies and says each rabbit is stuffed with her parents' love. The next morning, however, they are anything ''but'' loving, and the housekeeper tells the girl the only reason her mother had her was to replace a pet rabbit that died. The girl violently snaps, and later that night she cuts open her parents with a pair of hedge trimmers before tearing the stuffing out of the rabbit toys and stuffing into their dead bodies. It's implied she does the same thing to the housekeeper to "share" her parents' love.
* In ''Anime/PuellaMagiMadokaMagica'', [[spoiler:Homura failing to save Madoka from dying. And she's stuck in a GroundhogDayLoop, so she keeps failing]]. Fun!
* ''Manga/RurouniKenshin'': Kenshin is still wracked with guilt over, among other things, [[spoiler:not being able to protect his first love, Tomoe]]. This is magnified in the manga's Jinchuu arc when he apparently [[spoiler:fails to protect the woman he loves a second time (after Enishi fakes Kaoru's murder)]]. He eventually recovers, though, and finds out she's still alive as a reward.
* ''Anime/StrainStrategicArmoredInfantry'': Sara's post-traumatic stress syndrome is only worsened when [[spoiler:Carris]] dies too.
* In ''Anime/SwordOfTheStranger'', Nanashi has more or less sworn off drawing his sword. What makes this interesting is that his failure is MORAL rather than Physical. [[spoiler:He executed two children, by power of peer pressure. It's hard to disobey orders when surrounded by an army. Part of a military action, it's unclear the exact circumstances but it was likely a coup d'état. Nanashi only draws his sword in the eleventh hour in a last desperate attempt to save Kotaro, who strongly resembles the boy Nanashi executed]]. [[spoiler:By BITING THROUGH THE PEACE KNOT WHILE RUNNING AT FULL SPRINT ACROSS ROOFTOPS IN THE SNOW TO THE CROWNING MUSIC OF AWESOME]].
* ''Webcomic/TowerOfGod'': For Hon Akraptor, his inability to save his daughter is what drives him to climb the Tower.
* In ''Anime/YuGiOhArcV'', Yuzu Hiiragi is hit with this though the early episodes - the You Show School is on the line against LDS with a 3 vs. 3 match and while Yuya wins his match, Yuzu loses hers due to the fact that she's been distracted by the encounters with the mysterious boy who resembles Yuya. When Gongenzaka forces a tie, leading to Yuya and Reiji to have their first match, one that ends with a tie but Yuya takes harshly because Reiji used Pendulum Summon. She feels that, had she not been distracted, this wouldn't have happened.
* ''Anime/YuGiOhGX'': Season 3 has been one big Greatest Failure for Judai, ironically originating from his insecurities about [[TheAce never failing]].
* In ''Manga/YuYuHakusho'', [[spoiler:Younger Toguro]] is a DeathSeeker because he felt he couldn't suffer enough after a demon killed his students.

[[folder:Comic Books]]
* ''ComicBook/AntMan'': The villainous robot Ultron was supposed to be Henry Pym's greatest failure, but it never seemed to take; later, he was given much more depressing sorts of failures to worry about (such as abusing his wife, betraying his teammates, and repeatedly going insane), while Ultron eventually (for a time, anyway) became more of a ludicrous than ominous figure.
** During his tenure on ''Comicbook/TheAvengers'', Creator/KurtBusiek did a good job of finally making Ultron into a credible threat, up to and including having him wipe a country's population off the map. Pym's destroying the primary unit with a metal disruptor, and a subsequent character arc that involved quite literal split personalities were ''supposed'' to finally put Pym's demons to rest and let him start growing as a character again without the existence of Ultron and his other failures to continue hindering him. Yeah... not so much. Later writers actively regressed his sanity, brought back Ultron ''more than once'', and had him replaced by an alien who [[spoiler:tried to kill his ex before Thor accidentally turned her into a dimension, which Pym is obsessively trying to fix at the cost of his relationships with his team and Jocasta]]. As of the most recent Avengers stories, he's possibly even more screwed up now than he was then.
** As revealed after Jan's death in ''ComicBook/SecretInvasion'', Hank considers the worst thing he's ever done to be hitting his wife -- and he admits that, given everything else that's happened, that's saying something.
* ''Franchise/{{Batman}}'':
** Batman himself has blamed himself for a lot of things over the years:
*** Bruce blamed himself for the death of sidekick Jason Todd aka the second Robin. In the animated ''WesternAnimation/BatmanUnderTheRedHood'', he specifically uses the phrase "my greatest failure" in reference to Jason's death. Some versions of Batman's story have him blaming himself for the death of his parents. (In ''Film/BatmanBegins'', Bruce blames himself for the death of his parents, as they encountered Joe Chill after leaving the opera ''Mefistofele'' due to the performers triggering Bruce's fear of bats.)
*** That's not the only form of blaming himself for his parents - in some comics versions, he convinced his mother to wear pearls to the show, and those pearls are the reason they get robbed and shot.
*** He also blames himself for the creation of Comicbook/TheJoker, since he knocked him into the acid; the torture of Stephanie Brown, because he lost control of Gotham during "War Games"; and the death of [[ComicBook/BlueBeetle Ted Kord]] by Max Lord who hijacked Batman's creation, Brother Eye, to find Ted.
*** In some continuities, at least, there's also Harvey Dent, who Batman saw as a friend and ally that could really clean up Gotham in ways he himself could not - until Harvey became Comicbook/TwoFace.
*** For a time, he considered making Jean-Paul Valley Batman this, saying that it was done at a moment of weakness and it was a mistake. Really, this guy has so many of these that he's got a full-blown GuiltComplex.
*** When Jason Todd came back and because ComicBook/ThePunisher-like vigilante "Red Hood", that was another thing that Batman blamed himself for. He found Todd's descent into "lethal justice" so abhorrent that, in the story "Battle for the Cowl", his last will and testament address Jason with "You're broken, and I couldn't fix you. Maybe someone else can." Mind you, [[WellDoneSonGuy that wasn't exactly the best thing to say to him]] and it drove Jason even ''further'' over the edge, something else that Batman would have justifiably blamed himself for if he were still around.
** Commissioner Gordon has his role in the creation of [[EvilCounterpart the original Wrath]]: The same night Bruce's parents were murdered, a rookie Gordon got into a firefight with a couple who'd bought their son along as they committed a crime, which ended with a wounded Gordon killing the parents in self-defense, which in-turn led to the kid becoming the Wrath. ''Batman Confidential'' # 13-16 added to this, revealing that one: the original Wrath's father was among the many {{dirty cop}}s in the GCPD, two: a then-Captain [[ComicBook/BatmanYearOne Gillian Loeb]] covered it up to save his ass and those of the other corrupt officers, and three: Loeb forced Gordon to comply with this and a transfer to Chicago by threatening the kid's life.
** Alfred has always regretted that he didn't do more to help Bruce emotionally work through his parents' deaths, culminating in Bruce becoming Batman. In one particularly poignant scene in ''Dark Victory'', he resolves not to make the same mistake with the recently orphaned Dick Grayson.
* ''ComicBook/BlueDevil'''s greatest failure was making a deal with Neron (DC's ruler of Hell at the time) to gain fame as an actor in exchange for destroying an electrical substation in the desert. This resulted in the death of his best friend Marlene Bloom, whose helicopter crashed because of the blackout. This would come back to bite Blue Devil again years later when Marlene's nephew and Blue Devil's sidekick Eddie Bloomberg/Kid Devil found out after making a deal with Neron for powers. This resulted in Eddie losing his trust in Blue Devil and Eddie eventually losing his soul to Neron once he turned twenty.
* ''ComicBook/{{Chassis}}'': In her first professional race, Chassis [=McBain=] is forced to take evasive action due to a dangerous maneuver by ALEX Prime. In doing so, she collides with 'Rocketman' Rodriquez; forcing him off the track. Rodriquez collides with a pylon and is killed. This event haunts Chassis throughout her career and makes her always help racers in trouble, even if doing so causes her to lose the race.
* ''ComicBook/{{Circles}}'': Paulie's life-threatening mistake, [[spoiler:(accidentally contracting HIV)]], made him change his life around and now he lives as happily and as fully as possible.
* ''ComicBook/DisneyDucksComicUniverse'':
** In ''Comicbook/TheLifeAndTimesOfScroogeMcDuck'', Scrooge once hired a group of thugs to chase away an African tribe and burn down their village in an attempt to claim their land. This was the only time he ever made money dishonestly, and the resulting guilt (and zombie -- as in Bombie the Zombie) has haunted him ever since. He even became a depressed shut-in for the better part of twenty years until his nephews were able to re-ignite his spark, leading to the adventures we all know.
** Parodied in a Carl Barks comic; In one story, Donald Duck, Scrooge, and the nephews learn that Gladstone Gander has ''something'' locked in a safe that he never lets anyone see. They believe it's a charm that is the source of Gladstone's uncanny good fortune, but after much pressure, Gladstone admits its anything but; it's just a nondescript dime, the only salary he has ever earned from working, which he did during an unusually long dry spell in his luck. Gladstone is so smug about his luck providing him with everything that he considers the dime to be a symbol of his MomentOfWeakness and actually breaks down crying bitter tears as he tells the Ducks about it. (Who, BTW, are very close to caving in Gladstone's head at that point.)
* In ''ComicBook/{{Empowered}}'', the death of Mindf*** is this for both Emp herself and Sistah Spooky, both of whom tried, and failed, to save her.
* In the ''ComicBook/FantasticFour'', Reed Richards' own miscalculation and arrogance are what led to the titular team being hit by gamma rays and given superpowers. In the case of Reed, Sue, and Johnny, this is no big deal. But Ben's powers leave him a freakish rock monster and being trapped like that put a huge barrier between the two of them for years, in spite of being best friends. It wouldn't have been so bad if Ben could just change back from being The Thing, but StatusQuoIsGod so any changes back to a human are doomed to be short-lived. The fact that Reed is responsible for his friend's condition and cannot permanently cure him is something that has weighed heavily upon him his entire career. [[spoiler:When the team finds out that their transformation was caused by the ruler of a planet who was scared of their arrival and tried to force them back, Ben goes on a RoaringRampageOfRevenge because he realized that he'd blamed the wrong guy all along. Even when Ben finally buries the hatchet with Reed, Reed himself refuses to let it go privately and resolves to protect his family better.]]
** Also from the ComicBook/FantasticFour is the supervillain Doctor Doom. Doom built a machine that would allow him to communicate with the spirit of his dead mother and was told beforehand by Richards that it would critically fail. But when he ignored this, that's exactly what wound up happening and left his face scarred. [[NeverMyFault Years later he still can't accept that it was his fault it happened]], and [[DisproportionateRetribution devotes his life to killing Richards after convincing himself he must have tampered with the machine]].
*** The very different reactions of two characters who had initially been NotSoDifferent to their respective greatest failures exemplify the fundamental difference between them: Reed acquires a long-lingering GuiltComplex and dedicates himself to WithGreatPowerComesGreatResponsibility, which frequently torments him with ItsAllMyFault. Doom descends into a spiral of GreenEyedMonster and {{Revenge}}, unrelenting in his insistence that it's NeverMyFault.
*** DisproportionateRetribution indeed. In the original telling at least (Lord knows how many retcons may have flip-flopped since then) Doom didn't create the mask to hide a hideously mauled hamburger-face; he did it because the explosion left a ''thin, barely noticeable'' mar on his supposedly "perfect" facade. A man that vain, you could almost understand making some sort of covering... unfortunately in his haste, he didn't wait for the mask to cool before putting it on, which (DependingOnTheWriter) either DID hideously scar his face, or ''permanently bonded the mask to his skin''. He might not admit the accident itself, but he DOES (very rarely) admit to the fact that putting the mask on so fast wasn't his smartest idea.
*** Actually all this was based on John Byrne's retcon of the Lee/Kirby origin, based on an idea by Kirby that either Creator/StanLee had discarded or Creator/JackKirby only had it after the original version was published in ''Fantastic Four Annual'' #2 (1964). There, Doom's head is completely bound up and hidden beneath bandages and in the caption Stan Lee unequivocally states: "As for Victor Von Doom... his face was hopelessly disfigured!" Also on the page after that, even though the mask is not completely cooled when it is put on Doom's face, it is cool enough for the monk to hold it in his bare hands (you can easily discern his fingernails, etc.) By the evidence of that Annual, all the mask likely did was singe Victor's eyebrows.
*** In a ShockingSwerve, it now turns out that Doom's disfigurement is actually Ben's greatest failure. After years, he admitted that he had purposefully sabotaged Victor's machine after seeing how badly he treated Reed, and thus was presumably the one responsible for his transformation into Doctor Doom. During ''Comicbook/AgeOfUltron'', Ben claims he's wrestled with the guilt for years but is too terrified to tell anyone what he did.
* The plot of the comic series ''ComicBook/{{Fell}}'' is essentially watching Detective Fell right after his greatest failure, one that resulted in his banishment to his city's {{Shadowland}}, a [[UrbanSegregation ridiculously poor and crime-ridden slum]]. Most of the comic so far revolves around whether the already overly intense Fell, ([[TheProfiler who may be a little too good at getting inside the head of psychos]]) [[BreakTheHaughty will snap in his exile]], get killed, or come out of it redeemed.
* From ''Franchise/TheFlash''
** The third Flash's ally-turned-enemy, Zoom (Hunter Zolomon), acknowledged this in a twisted way. He felt that Wally required a tragic failure to be a great superhero -- even if Zoom had to make one for him. He later made good on his promise by causing the Flash's wife to miscarry the couple's unborn twins, right in front of the hero's eyes. The twins were later restored to life by the miracle of TimeTravel, but the Flash still blames himself for Hunter becoming a villain in the first place, as Hunter had asked him to use time-travel to "fix" his past, which Wally declined.
** A future version of Barry Allen (the second Flash) regretted getting Wally West II killed, and it sent him over the edge. He time-travels backwards through time, murdering his villains along the way, and arrives in the present to prevent ''any'' criminals from committing any crimes, whether they've done them yet or not.
* From ''Franchise/GreenLantern'':
** Hal Jordan, UsefulNotes/{{the Silver Age|of Comic Books}} Green Lantern, was away in space when his home city of Coast City was destroyed. He went crazy and became a villain, Parallax, dedicated to undoing the destruction through gaining cosmic power, time travel, or just rebooting the universe itself. (It was [[RetCon later revealed]] that the great failure had let an ancient evil trapped in the Central Power Battery of the Green Lantern Corps get a foothold on his mind.)
** Additionally, John Stewart, UsefulNotes/{{the Bronze Age|OfComicBooks}} Franchise/GreenLantern, had this moment with the [[EarthShatteringKaboom destruction of the planet Xanshi]], being way too overconfident with his power, apparently [[WhatAnIdiot forgetting]] the [[AchillesHeel weakness to yellow]], as the bomber painted the planet-killing bomb yellow. This depressed him so much that he contemplated suicide. (The ComicBook/MartianManhunter thankfully prevented that, through ReversePsychology). The end result was a guilt that would haunt him forever, and the creation of Fatality, the [[LastofHisKind sole survivor of Xanshi]], who was off-world at the time, who now [[RoaringRampageOfRevenge hunts Green Lanterns as revenge]].
** Another Green Lantern, Kyle Rayner, had his mother die of an unknown fatal disease. Even when Kyle, with God-like power, tries to resurrect her, she asks to be allowed to die. During the "Sinestro Corps War" {{Arc}} [[spoiler: Sinestro reveals to a captive Kyle that her death was the work of a sentient alien virus working for the Sinestro Corps, and was all part of a plan to make him vulnerable to possession by Parallax]].
*** That was Kyle's ''second'' Greatest Failure. The first came early in his career when his girlfriend Alexandra [=DeWitt=] was killed by Major Force in the original StuffedIntoTheFridge incident. Up until then, Kyle thought having a super-powered ring would be fun and a lot of laughs, but when that happened, Kyle grew up pretty fast.
** Green Lantern Tomar-Re's greatest failure was failing to stop Superman's home planet of Krypton exploding. Krypton fell under Tomar-Re's jurisdiction, so he gathered a bunch of Stellarium to absorb the explosion, but got blinded by a solar flare and did not make it in time.
* John Constantine, ''ComicBook/{{Hellblazer}}'', botched a summoning and caused a little girl to be dragged down into Hell. This hung over him for years, until he was able, thanks to some clever manipulation and trickery, to free her soul and the soul of every other child in Hell.
* In the ''Franchise/MarvelUniverse'', ComicBook/CaptainAmerica originally was plagued with guilt about his sidekick, [[ComicBook/BuckyBarnes Bucky]], being killed when he could have spared him by not allowing him to be his sidekick. However, the writers realized how old that got and had Cap's later protégé, Rick Jones, demand he get over it and move on. Furthermore, that guilt was replaced by the writers with Cap troubled by [[BadPresent the state of the nation]], which is at least more sophisticated and flexible a concern to use. Having said that, Bucky's death still influenced his interaction with younger [=superheroes=], notably Franchise/SpiderMan. His guilt came back when it turned out that Bucky survived, only to have been found by the Soviet Union and [[ReforgedIntoAMinion turned into the Winter Soldier]]; an elite assassin responsible for multiple murders. Cap considered this a fate worse than death and did his best to break his mental conditioning. Even afterwards he felt responsible for Bucky's well-being and [[spoiler:put in his will that Tony should do his best to save him after he died]].
** His [[ComicBook/UltimateMarvel Ultimate version]] ends up feeling just as guilty if not more so, due to [[spoiler:telling teenage Peter Parker that he wasn't ready to be a hero, causing him to [[HeroicSacrifice be more heroic than he ever had been before]]. The fallout, coupled with [[WhatTheHellHero a lecture from an angry Aunt May]], made him retire from superheroics altogether]].
** Bucky himself feels that his time as the Winter Soldier can be summed up as this, but the biggest seems to be his killing of the Bucky that replaced him. Not only because he killed the guy, but because, if Bucky had never become Steve's sidekick, then he wouldn't have inspired his replacement to begin with.
* ''ComicBook/{{Nightwing}}'' had a moment revealed following ''ComicBook/ZeroHour''. When he was Robin, it was up to him to rescue Batman and the DA that replaced Harvey Dent when he became Two-Face. When he confronted the aforementioned villain, he was planning to hang both of them for their "crimes". Two-Face attempted to hang the DA and Robin responded by cutting the line with a Batarang. However, he didn't realize that Two-Face's MO applied to everything - he saved the DA from hanging, but couldn't save him from ''drowning''. Batman freed himself and saved the day, but the event haunted Dick until the first time he took up the Mantle of the Bat, finally making the save when confronting Two-Face again.
** Nightwing also feels guilt over not only the crippling of Barbara Gordon but the death of Jason Todd. Both of them stemming from the fact that at the time both events happened Dick and Bruce had a falling out which resulted in Dick leaving Gotham and establishing himself as Nightwing. He has notably taken a [[BigBrotherMentor far more proactive role]] in mentoring subsequent members of the Bat-family (as well as serving as leader of the [[ComicBook/BatmanAndTheOutsiders Outsiders]] and a key ally to the ComicBook/BirdsOfPrey).
* ''ComicBook/ThePunisher'' 's greatest failure was [[DeathByOriginStory the loss of his family]], for which he blames himself as much as the mobsters who gunned them down, believing that he should have been able to protect them. His war against criminals is as much to punish himself as it is to punish them.
** Punisher himself is considered a Greatest Failure by his on-again-off-again ally ComicBook/{{Daredevil}}, who was one of the first heroes the Punisher encountered (after ComicBook/SpiderMan) and who he is closely associated with. Daredevil regrets having been unable to pull Frank back from the brink when they met early in their respective careers and feels obligated to at least try and stop Punisher's endless blood bath.
* ''ComicBook/{{Runaways}}'' has several examples:
** Nico has occasionally been shown to regret her rejection of Karolina's advances. She was also not proud of her decision to sleep with Victor.
** Xavin regrets his[=/=]her role in the war between the Skrulls and the Majesdanians.
** Chase is still haunted by Gert's death and has tried on at least two occasions to undo it. He also used to feel guilty about the time he apparently ran over his uncle, but then his uncle turned up alive a few years later.
** In ''ComicBook/AvengersAcademy'', Klara is shown to blame herself for [[spoiler:Old Lace's]] death, to the point that she's become somewhat more aggressive in protecting her friends.
** [[spoiler:Lillie [=McGurty=] has spent the past 90-plus years regretting her decision not to follow the Runaways into the present. It's unclear whether or not she's also aware of her role in the deaths of most of her friends and the horrible maiming of [[UnluckyChildhoodFriend Tristan]]]].
* In ''ComicBook/TheSandman'', the immortal Hob Gadling will never forgive himself for having made his fortune in the slave trade.
* In the ''ComicBook/SonicTheHedgehog'' comic, it's recently been revealed that Monkey Khan was [[spoiler: taken control of by the Iron Queen and forced to eliminate the Freedom Fighters in the Dragon Kingdom]]. Understandably, he harbors massive guilt toward himself and hatred for [[{{Magitek}} the Iron Queen]], to the point where he was angry at Knothole for holding a celebration when she had taken control of the Eggman Empire.
** Robotnik caused a ''lot'' of this. He caused the accident that resulted in Nate Morgan being exiled from the Overlanders' city, and years later, was saved from the overlanders by Jules and Sir Charles the Hedgehogs. He also banished Kodos to the Zone of Silence, sabotaged Sir Charles' roboticizer (resulting in Jules becoming a robot), took over Mobotropolis from King Acorn...
* ''Franchise/SpiderMan'':
** Spider-Man didn't stop the burglar that would shoot his Uncle Ben (in various tellings, because of spite, laziness, or arrogance); later, he was [[ComicBook/TheNightGwenStacyDied unable to prevent his girlfriend Gwen Stacy from being killed]] by the [[ComicBook/NormanOsborn Green Goblin]]. The latter is not helped by how his using his webbing in an attempt to save her caused her neck to snap from the recoil, a fact Marvel initially attempted to gloss over but has recently admitted (through, among others, ''What If?'' - where he saves her by diving in after her instead - and ''ComicBook/SpiderGirl''). It's made pretty clear that he at the very least thinks this is what happened, as he makes it a point to use multiple weblines when saving people, and Iron Man recalls Peter telling him of the incident.
** Speaking of Spider-Man, for his foe J. Jonah Jameson, it was definitely the Scorpion. Jonah paid private eye [=MacDonald=] Gargan to undergo an experiment that would make him strong enough to subdue and defeat the hero. The scientist conducting the experiment warned both of them that he "didn't know how it will affect your brain" but they went ahead with it anyway; true to the scientist's fears, Gargan was driven insane, becoming more of a threat than Spider-Man could ever become. Jonah has never even tried to blame this on Spider-Man (at least in any convincing way); after the Hobgoblin tried to blackmail Jonah about Gargan, the publisher has taken full responsibility for the villain, and to this day, pays for Gargan's psychiatric treatment out of his own pocket and orchestrates compensations funds to aid victims of the villain's crimes. And to make it worse for Jonah, Gargan hates him even more than he hates Spider-Man for what happened to him.
** In the ''[[ComicBook/UltimateMarvel Ultimate]]'' universe, he considers his treatment of Spider-Man to be his greatest failure. He was visibly distraught when the hero sacrificed his life to stop ComicBook/NormanOsborn, and later admitted that he spent all that time and money essentially hounding a good kid who just wanted to make the world a better place. His guilt over Peter's death is what later motivated him to protect the identity of [[AffirmativeActionLegacy Miles Morales]], the new Spider-Man.
** ComicBook/MaryJaneWatson felt incredibly guilty over having essentially abandoned her sister when their mother died and left her to take care of two children by herself because MJ was afraid of spending the rest of her life sacrificing her own dreams for everyone else like her sister and mother had.
* ''ComicBook/{{Supergirl}}'':
** During a talk with Guy Gardner in ''ComicBook/RedDaughterOfKrypton'', Kara confesses that she feels guilty for Krypton's destruction, even though she intellectually knows there was nothing she could do to save it.
--->'''Supergirl:''' And now Krypton's lost forever. There was nothing I could do to save it, but it feels like I'll be trying to make up for that the rest of my life.
** In ''ComicBook/{{Bizarrogirl}}'', Supergirl blames herself for being incapable of saving her family and her race when ComicBook/NewKrypton got blown up.
* ''Franchise/{{Superman}}'':
** At various points in his history, Superman has had the bottled city of Kandor to deal with.
** Superman also feeling really guilty of being unable to help his childhood friend, Mon-El, conquer his deadly weakness for lead and leave the Phantom Zone where he was cast into at his request as the only way to save his life.
** In ''Comicbook/WarWorld'' Superman blames himself because he has the power to do nearly anything... but saving Krypton or his foster parents. Even when he's got the chance to save them, he failed.
** During UsefulNotes/{{the Silver Age|of Comic Books}} and UsefulNotes/{{the Bronze Age|OfComicBooks}}, Superman's biggest failure was arguably when he destroyed Comicbook/LexLuthor's protoplasmic lifeform that he created as well as causing his hair to fall out when he was trying to rescue Luthor from a lab fire when they were teens. Sure it was an accident and mostly not his fault (Luthor caused the fire and Superboy had no way of knowing what was inside at the time), but it didn't help that before the fire, Superboy jokingly said he could spy on Luthor to find out what he was working on. Luthor wrongly believed Superboy destroyed his experiment out of jealousy and dedicated his life to destroying him and proving he was better. Luthor had the scientific genius to make a cure for Kryptonite as well as unshrink Kandor, so if things had gone differently, Superman would have had a lot fewer problems in his life and an ally against evil as well.
** A painful one for Superman happened just after his resurrection in ''Comicbook/TheDeathOfSuperman''. After the excitement and relief of him returning from the dead, he and Lois raced off to Paris for a getaway to catch up. While he was gone, the Toyman kidnapped a bunch of kids, including the son of co-worker Cat Grant, Adam. Adam attempted to lead the other kids away, but Toyman caught them and slew them all. Superman was so distraught over this, it led to him vowing never to take another vacation again.
** Another one was when one of Luthor's schemes leveled Metropolis to the ground. [[ComicBook/LoisLane Lois]] had to snap him out of it, reminding him that this wasn't [[Franchise/GreenLantern Coast City]] and Metropolis could be rebuilt. It was, [[AWizardDidIt thanks to]] ComicBook/{{Zatanna}}.
* In ''ComicBook/TopTen'', Jeff Smax never really got over his failure to save a little princess from a dragon. Her handprint was permanently burned onto his chest and would serve as a constant reminder of how big a screw up he was. Immediately after it happened, he informed the queen and ran away. Across dimensions. To a world nothing at all like the one he came from. Even changing his name. Only after [[ComicBook/{{Smax}} a necessary return to his homeworld]], where the dragon was slain and the handprint was erased, could he let it go, and only a little.
* Optimus, and later Megatron, both consider the 6 million year Great War this in ''ComicBook/TheTransformersIDW''. Optimus blames himself for not taking a stand against [[FantasticCasteSystem society earlier]]. Megatron for abandoning his ideals and becoming a monster over the course of the war. Many transformers, Autobot and Decepticon, echo these views.
* ''ComicBook/XMen'':
** ComicBook/{{Rogue}} for a long time lived in deep guilt and remorse over what she had done to [[ComicBook/MsMarvel Carol Danvers]]. She was able to finally work past it, especially after Ms. Marvel was reintegrated with the stolen thoughts and memories through AppliedPhlebotinum.
** ''ComicBook/{{X 23}}'' continues to be haunted with guilt and remorse over killing her mother in a trigger scent-fueled rage during her escape from the Facility, to the point that when Logan finally manages to bring her to the Xavier school, Emma Frost tries to drive her away by taunting her with a psychic ghost of her mother's dead body blaming Laura for her death. The illusion is shattered when the "Sarah" calls her "X-23," but it's still enough to drive the [[NotSoStoic normally stoic Laura to tears]].
** ComicBook/{{Gambit}} has the fact that, to repay a debt to Mr. Sinister, he was forced to help gather a group for Sinister to execute a task -- that being Remy got suckered into helping form the Marauders for the fateful massacre of the Morlocks and maiming of Angel in ''Mutant Massacre''.

[[folder:Fan Works]]
* Downplayed in ''Fanfic/AVoiceAmongTheStrangers'': Captain Swift Dawn, one of the Royal Guards assigned to protect Jessica, loses track of her in Baltimare, and she almost gets recaptured by the Flim Flam brothers. He rescues her and ends up [[TakingTheBullet shielding her from a whip]], leaving him with a scar across his muzzle. Jessica later learns that he refused to have it healed so that it would be a constant reminder of his near failure.
* ''Fanfic/AncientSins'': During their fight, Celestia remarks that she had immense pride in Dante when he was younger, but is now ashmed at his fall from grace.
-->'''Celestia''': I remember when you were younger. You had so much potential, but you allowed darkness to wrap around your heart. You were my greatest hope, but you became my biggest regret.
* Asha al'Wahim's ancestor from the ''Franchise/MassEffect''[=/=]''Franchise/AvatarTheLastAirbender'' crossover ''FanFic/AvatarOfVictory'' was actually a pretty good general, until he made a mistake during the First Contact War that got the previous Avatar killed. As such, her entire family is considered jinxed, and she takes it upon herself to [[TheAtoner try and regain some of her family honor]].
* In the ''Franchise/BackToTheFuture'' fanfic ''Fanfic/BackToTheFuturePrequel'', Doc still regrets the day [[spoiler: one of his inventions malfunctioned and crippled Holly Webb]].
* For [[NominalHero Naruto]] in ''[[https://www.fanfiction.net/s/3665921/50/ Black Flames Dance in the Wind: Rise of Naruto]]'' he has two for the price of one. Defeating a powerful demon accidentally caused a horrific attack on Konoha that resulted in scores of deaths, if not hundreds. Then dealing with said attack caused him to forget about Anko who very nearly died before she was found. Worse is that Anko was only still alive due to taking multiple blood pills to replenish her lost blood, so she was conscious for the entire day she was tortured to the point of near-death. Even weeks later, Naruto is clearly tortured by his "abandonment" of Anko, at one point writing "I left her behind" on the written portion of the Chunin Exam.
* ''Fanfic/TheBridge'':
** Godzilla Junior deeply regrets not being able to defeat Destroyah the first time they fought, as that led to his father Godzilla Senior fighting her and his death.
** Back when they were active soldiers, Stalwart Sentry and Fancy Pants [[spoiler:arrived too late to prevent a dragon from killing Starlight and Moonbeam Glimmer's parents and neighbors. Though they were able to save the girls and kill the dragon, the event still haunts them]].
* In the ''Literature/HarryPotter'' story ''Fanfic/CruciamentumEternus'', Lucius fails to stop Voldemort from killing Draco, conducts a HeelFaceTurn, and spends years trying to make up for it.
* In ''Fanfic/TheDearSweetieBelleContinuity: Dear Scootaloo'', Rainbow Dash seems to view failing to save [[spoiler:Applejack's parents]] from the Great Storm as this- at least, when she gets a note worded as such from the one responsible for said storm, she knows what he's talking about.
* In ''Fanfic/EmpathTheLuckiestSmurf'', Papa Smurf sees taking [[spoiler:his only begotten son]] Empath to Psychelia where he was forcibly taken from him by the Psyche Master, and then having to hear [[FakeKillScare the child's "dying" screams]], as this. While it would lead to his wife separating from him and [[HeroicBastard having Brainy]] with another Smurf, it would also lead to his redemption when he became the sole parent of about a hundred orphaned young Smurfs whose parents died in ThePlague that was OnlyFatalToAdults.
* ''Manga/{{Evangelion 303}}'': This is how Asuka sees [[spoiler:the Unit-04's crashing]]. Even though it was not her fault, she considers herself responsible for the failure of the mission and [[spoiler:her best friend's death]].
* In ''Fanfic/FateZeroSanity'', [[LadyOfWar Saber]] has two: Her canon failure to prevent Camelot's fall and [[spoiler: her role in [[WellDoneSonGuy Mordred's]] betrayal, [[IHaveNoSon refusing to acknowledge her as her successor]] due to her bitterness against Morgan le Fay]]. The later is only revealed after she fights [[spoiler: an [[YourMindMakesItReal illusion of Mordred]] created by a trap left by Assassin]].
* In [[https://www.fimfiction.net/story/50850/1/innocence-once-lost/a-new-world Innocence once lost]] Rainbow Dash blames herself for Fluttershy losing a leg during the war. She was showing off dodging enemy fire and forgot Fluttershy was flying behind her, she didn't warn Fluttershy to dodge and one of the projectiles hit her.
* ''Fanfic/LifeInManehattan'': Orange Sherbet sees her failure to be able to properly bond with Applejack during her stay in Manehattan as her biggest failure. [[spoiler: Turns out, Applejack sees walking out on her aunt as hers]].
* ''Fanfic/LovedAndLost'': Due to being banished from Equestria as [[HeroWithBadPublicity hated pariahs]], Princess Celestia, the Mane Five, Shining Armor, and Spike express deep regret over mistreating Twilight and inadvertently causing the Changeling invasion. This motivates them to return to Canterlot so that they can [[MustMakeAmends clear their names and make amends]].
* ''[[FanFic/JusticeLeagueOfEquestria Mare of Steel]]'': Jor-El feels this way about being unable to cure his wife's lung condition. Rainbow Dash feels the same way about being unable to save her sick adoptive father from dying.
* In ''FanFic/MegaManDefenderOfTheHumanRace'', while Duo had failed to stop the Stardroids on occasion before, his greatest moment of doubt came when he watched them destroy a planet in front of his eyes.
* In ''FanFic/MegaManReawakened'', Police Chief Marmalade thinks his biggest failure is voting for Wily to have a bail sum at all.
* In ''[[https://www.fanfiction.net/s/11772125/1/Metroid-Kamen-Rider-Generations-Full-Series Metroid: Kamen Rider Generations]]'', just like in [[Series/KamenRiderGaim Gaim's post-series canon]] (listed below in Live-Action TV) Mitsuzane, for the rest of his life, will never live down the enormity of the sins he committed that culminated with Kouta and Mai's deaths. This portrayal of him is also coupled with [[ByronicHero Byronic traits]] led him to fight alongside Samus in her adventures.
** [[Series/KamenRiderDrive Chase's]] death at the hands of Banno is for Gou. [[spoiler:He got better when Chase is [[BackFromTheDead resurrected]]]].
** The deaths of [[spoiler:Gandrayda, Ghor, and Rundas]] are these for Samus when she mentions the events of ''VideoGame/MetroidPrime3Corruption''.
* ''Fanfic/MyHeroSchoolAdventureIsAllWrongAsExpected'': Hachiman regrets losing contact with [[OnlyFriend Zaimokuza]] after entering high school and never thanking him for letting him copy his HealingFactor Quirk, especially after learning that [[spoiler:Zaimokuza went missing and [[UncertainDoom likely died]] without Hachiman finding out until it was too late]]. This is the reason why he goes out of his way to be nice to Saki Kawasaki, another student who (albeit unwittingly) provided him with a Quirk essential to his heroic lifestyle. This is also why Hachiman is so determined to do everything he can in the U.A. Sports Festival to earn himself a spot on Hiratsuka's investigative team as they look into [[spoiler:Zaimokuza's disappearance]].
* This is the theme of the ''[[WesternAnimation/MyLittlePonyFriendshipIsMagic MLP:FiM]]'' fan-song ''Music/LullabyForAPrincess'', combined with Celestia [[ItsAllMyFault blaming no-one but herself]].
* In one subplot of ''Fanfic/PartingWords'', Applejack gets a very harsh wake-up call when she discovers how her lack of action (and good advice for that matter) with regards to the Cutie Mark Crusaders' bullying problem has essentially caused Applebloom to [[BrokenPedestal lose all faith in her]]. [[MustMakeAmends Learning from this mistake and fixing the damage this has done to their relationship]] becomes one of the focal points in the sequel ''Fanfic/TheGreatAlicornHunt''.
* In ''FanFic/{{Pretender}}'', Robin blames himself for [[spoiler:not saving Emmeryn]] and feeling that he failed as a tactician for not predicting the events that led up it, even telling Chrom to let her die instead of giving up the Fire Emblem.
* In ''FanFic/QueenOfAllOni'', a ''WesternAnimation/JackieChanAdventures'' fanfiction, Uncle views Jade's FaceHeelTurn as this, since he noticed the scar on her chi that allowed the Queen persona to be reawakened, but didn't do anything about it since he didn't feel it was a threat.
* Seen in ''Fanfic/ShepardsRR''. Commander Shepard chose the "[[KillEmAll Destroy]]" ending for Mass Effect 3, and although it saved the galaxy, it killed all the allied geth and his close friend EDI. He almost breaks down when he visits [=EDI's=] spot out of habit and remembers he caused her death, and it becomes a regular source of grief for the rest of the story.
* In the ''FanFic/TamersForeverSeries'', this is how Rika views [[spoiler: being unable to save Takato from dying in front of her]].
** Izzy also feels this way about [[spoiler: being unable to save Mimi from being kidnapped]].
* VideoGame/DragonAgeInquisition's ''FanFic/WalkingInCircles'': Solas, as per canon, considered his act of creating the Veil to be the biggest mistake of his life but by the time canon events start, he also considers what happened to Evelyn to be his ''other'' greatest failure. As he put it, he promised to save her but in the end, it was always her who saves him and she has to suffer for that, yet she has never once blamed or hated him and still chooses to accept him which only further his GuiltComplex.
* Professor Oak's in ''[[https://www.fanfiction.net/s/12840662/1/Shudo-cross-Modern-Ash-The-Professor-Who-Observes-his-Charges Shudo cross Modern Ash: The Professor Who Observes his Charges]]'' is the fact that his son, Gary's father, grew to hate him because the Professor did not know he was conceived. While the Professor did try to reconcile, it did not go well and his son died hating him.
* ''Fanfic/ProdigalSon'': It is not until after one of the children under his supervision dies in the arena during training does Gobber retire from training, passing on that responsibility to Astrid.
* ''Fanfic/WeightOfTheWorld'': Having found a [[spoiler:Silver-Eyed Warrior]] for the first time in decades, Ozpin became foolishly overconfident and reckless in his fight against Salem. [[spoiler:Summer Rose]] paid for his arrogance with her life and Ozpin vowed not to make the same mistakes again.
* [[https://i.redd.it/yhq38d3ui8x11.png This fanart]] makes the case that Superman's greatest failure isn't his inability to redeem Lex Luthor, save Krypton, enlarge Kandor or eradicate crime... but his total and complete failure to protect his family.
* ''Fanfic/ApotheosisMHA'': All Might's is VillainProtagonist Izuku Midoriya's descent into evil. A MomentOfWeakness and a lack of tact led to him crushing the dreams of his greatest fan and turning him into Japan's worst supervillain since All For One. The worst part is that All Might didn't even ''[[ButForMeItWasTuesday remember]]'' Izuku until he became a possible suspect for the titular Apotheosis's civilian identity. His guilt over the situation ultimately becomes a double-edged sword: while it drives him to stop Izuku before finally passing One For All onto a successor, it also prevents him from doing what is necessary to take Izuku down.
* Gligarman in ''Fanfic/PokemonResetBloodlines'' considers his greatest failure having not stopped the children of the criminal Heratia from killing her in front of his eyes. From that day onwards, he vowed to never let anybody die in front of him ever again, not even a criminal he's trying to stop. The next time it happened, he retired from crimefighting for a long time.
* In ''[[https://www.fanfiction.net/s/13224343/13/Metallurgy Metallurgy]]'', All-Might considers the USJ to be his greatest failure as using up most of his time dealing with petty crimes and joyriders beforehand resulted in Izuku losing a hand to Shigaraki.
* ''Fanfic/BloodMoon'': Sokka harbors a considerable degree of self-loathing for his failure to prevent the Fire Nation from capturing Katara.
* ''Fanfic/OneDayAtATime'':
** Damian's death is implied to be this for Jason. Jason was only present in the aftermath of Bruce's and wholly un-involved in the respective incidents that caused the deaths of Dick and Tim due to being busy with other pressing situations when they happened. Cass and him, however, were there when Damian made his HeroicSacrifice, ending in him [[DiedInYourArmsTonight dying in their arms]]. Jason privately admits that out of all his siblings, Damian's death was always the one he regretted the most.
** [[spoiler:The death of Joker III. Jason considers killing the third Joker to be the biggest mistake of his life, because it led to the rise of Joker IV, who ultimately killed Bruce]]. He fully admits that there isn't a day that goes by where he doesn't think about what life would've been like had he never pulled that trigger. It was this event that caused Jason to become more family-oriented and, most noticeably, [[ThouShaltNotKill give up killing]].
** Dick's first great failure during his tenure as Batman were the deaths of Kate Kane and Renee Montoya during the Bat-Family's war with the Court of Owls. It's all but stated that their deaths are what drove Dick to be so obsessed with removing the Court from Gotham.
** Dick's other, more noticeable failure is the deterioration of his relationship with his brother Tim. [[spoiler:In one timeline, this led to Tim making a FaceHeelTurn and traveling back in time to both brainwash the world and personally murder Dick]].
** When [[spoiler:Death of the Endless]] first forged [[spoiler:[[ImmortalBreaker the Balance]]]], the first wielder she chose was a warrior of great renown who she instructed to [[spoiler:kill all immortals]]. He did exactly that -- [[spoiler:and then started murdering innocents to keep seeing her, as he had fallen in love with her. A horrified Death promptly marked his soul when he died so he would be DeaderThanDead and chose the next wielder much more carefully]].
* Integrity's death is this for [[VideoGame/{{Undertale}} Sans]] in ''Fanfic/NotAsSimpleAsAHappyEnding''.
* ''Fanfic/HereThereBeMonsters'': Several millennia later, the wizard ComicBook/{{Shazam}} still considers giving [[ComicBook/BlackAdam Teth-Adam]] powers was his biggest mistake.
-->Even so, he had seemed old when he bequeathed his powers in ancient times to Teth-Adam, which was a great mistake. Then, millenia later, he gave those powers to the three youths, which was anything but a mistake.

[[folder:Films — Animation]]
* Played with in ''WesternAnimation/TheBookOfLife''. Manolo's father tells his son when he is very small that he will grow up to be the greatest of the Sanchezes. But when Manolo [[spoiler: refuses to kill the bull]], he reacts [[IHaveNoSon very badly]]. But when Manolo lives up to his heroic destiny, his father says that Manolo has indeed become the greatest of the Sanchezes.
* In the climax to ''WesternAnimation/DespicableMe'', when Gru is trying to save the girls from Vector, Margo angrily yells at Gru that he had abandoned them before, making her hesitant to jump to him now. Gru admits, with obvious self-loathing, that said abandonment was the worst thing he had ever done. However, he also says that [[MyGreatestSecondChance he'll never do anything like that again]], and he follows through when Vector comes in to try to keep Margo.
* In ''WesternAnimation/FindingNemo'', Marlin holds a great regret of having failed to protect his wife and multiple unborn children from a Barracuda attack, causing him to become overprotective of his only surviving son, Nemo. It's the journey to get him back that allows Marlin to let go of his guilt, having realized that his attempts to protect his son nearly got him killed.
* ''WesternAnimation/Frozen2013'' sees Elsa harbor a great deal of shame for her powers nearly killing her sister on accident when they were children, causing her to become cold and distant from Anna as they got older. [[spoiler: It's thanks to the events of the film that she's able to overcome this and rekindle her relationship with her sister, allowing her to move on with her life free of the guilt.]]
** However, this comes right back around in ''WesternAnimation/FrozenII'' when Elsa and Anna's quests to Northuldra lead them to learn [[spoiler: the journey on which their parents died was because they were attempting to try and learn the cause of Elsa's powers]], causing Elsa to blame herself for what happened to them. [[spoiler: Again, it's the film's events that allow her to move past this regret.]]
* Mr. Incredible in ''WesternAnimation/TheIncredibles'' blames himself for spurning Buddy (later known as Syndrome), his biggest fan. Later, Buddy turns to evil. Subverted as Buddy points out that Mr. Incredible hadn't given him a single thought until he became Syndrome.
* In ''WesternAnimation/MyLittlePonyEquestriaGirlsRainbowRocks'', former BigBad Sunset Shimmer feels this way about her previous actions in [[WesternAnimation/MyLittlePonyEquestriaGirls1 the first movie]]. As an AlphaBitch who ran the school with an iron fist, Sunset's HeelFaceTurn has been met with [[ReformedButRejected rejection by the students of Canterlot High School]]. Even as Sunset tries to improve, her low self-esteem gets [[FlawExploitation exploited to keep her quiet]] after Sunset finds out about the plans of [[EnthrallingSiren the Dazzlings]].
* In ''WesternAnimation/TheMysteriousGeographicExplorationsOfJasperMorello'', Jasper is haunted by a recent airship voyage where a mistake in his calculations led to a collision and a crewman going overboard.

[[folder:Films — Live-Action]]
* In ''Film/{{Alien 3}}'', this is how Clemens got to Fury 161. He was previously a doctor, but he got addicted to morphine in medical school. When an industrial accident caused the deaths of a lot of workers, he was called in. Eleven people died not because of their injuries, but because he was so out of his head that he prescribed the wrong dosage of painkillers. He was jailed for seven years on Fiorina, and his medical license was reduced to a Class C. When the facility was due to be closed down but the inmates didn't want to leave, he elected to stay on as the medical officer. He got seven years for the act, but he considers this a light sentence.
* ''Film/AvengersEndgame'':
** [[spoiler:'''Everyone''' feels this way about Thanos killing half the universe, but Thor has it the worst. At the end of the previous movie, he struck a lethal blow on Thanos. For all intents and purposes he had won, but he decided to gloat instead of finishing Thanos off. This gave Thanos a chance to use the Infinity Stones and kill half the universe. Five years later, Thor is a fat, drunken wreck who does nothing but watch tv and intimidate a teenage gamer online]].
** [[spoiler:Tony has one of his own: his inability to stop Thanos cost [[Franchise/SpiderMan Peter Parker]], the young boy who he had taken under his wing and who became like a surrogate son to him, his life. After returning to Earth, the emotional trauma he suffered from Peter's death, combined with physical weakness upon his return and concern over the family he starts with Pepper in the five years since, leaves him reluctant to help the Avengers again until he resolves to try and bring Peter back.]]
* In ''Film/BatmanVSupermanDawnOfJustice'', before the events of the film, [[Comicbook/{{Superman}} Clark]] has the [[Film/ManOfSteel battle of Metropolis]], blaming himself for not being able to prevent all the death and destruction that Zod and his followers caused, while [[Comicbook/{{Batman}} Bruce]] has both the death of Comicbook/{{Robin}}, murdered sometime before the events of the film by Comicbook/TheJoker and Comicbook/HarleyQuinn, and the destruction of the Wayne Financial building in Metropolis during Zod's attack, which fuels a lot of his [[FantasticRacism hatred]] for Superman. During the film itself, Clark's greatest failure becomes [[spoiler: the destruction of the US Capitol building and the deaths of everyone inside, since he blames himself for not seeing the bomb that caused the destruction (although Comicbook/LoisLane discovers that Comicbook/LexLuthor hid the bomb behind lead, meaning that Clark ''wouldn't'' have spotted it even if he was looking for it)]], while Bruce's becomes allowing his fear and mistrust of Clark to become [[FallenHero hatred and cruelty]], allowing Lex to manipulate him and making him partly responsible for [[spoiler:Clark's death]]. However, Bruce [[MyGreatestSecondChance decides to learn from his mistakes]] and reach out to the other metahumans in friendship, bringing them together as a [[Comicbook/JusticeLeague team]].
* In ''Film/DieHard'', Al Powell admits in the movie that he can't shoot a gun anymore since he shot a kid with a plastic gun. By the end of the movie, however, Al ends up killing TheDragon with a gun.
* In ''Film/TheExpendables'', Tool tells Ross about a time in Bosnia during his mercenary days when he came across a woman about to throw herself off a bridge. He mentions he could have at least ''tried'' to save her, but since he was more concerned with just keeping himself alive until he could be evacuated, he simply turned and walked away, hearing her body hit the water as he left.
-->'''Tool''': She was gone, and after takin' all them lives, here was one that I coulda saved, but I didn't. And what I realized later on was if I'da saved that woman, I mighta saved what was left of my soul.
* ''Film/FearCity'': Matt Rossi is still reeling over the [[CasualtyInTheRing accidental death of one of his opponents]] when he was a boxer.
* In ''Film/FortyTwo'', this is the ''real'' reason why [[spoiler:Branch Rickey tirelessly fights for integrating Jackie Robinson into the Brooklyn Dodgers. Rickey's lifelong love of baseball was spoiled when he was unable to recruit a talented African-American player due to segregation]].
* In ''Film/GangOfRoses'', Rachel cannot forgive herself for the last bank robbery her gang pulled, which resulted in an innocent bystander being killed and her having (literal) blood on her hands.
* In ''Film/TheKarateKid2010'', Mr. Han's car accident [[spoiler: that killed his wife and son]].
* In ''Film/TheKiller'', Ah Jong/Jeffrey Chow felt this way after he accidentally blinded Jenny with a muzzle flash at the nightclub at the beginning of the movie and towards the child who he brought to a hospital after she took a bullet from one of the people out to kill him during the shootout at the beach.
* In ''Film/KingsmanTheSecretService'', Harry failed to properly pat down a mook prisoner to see if he was carrying a grenade, so when the prisoner attempts to blow up himself and the rest of the Kingsmen in the room, Eggsy's father pushed Harry out of the way and jumped on the grenade himself, taking the blast. Made even worse given how he was Harry's protégé.
* ''Film/TheMountie'': During a raid on a Chinese gambling den, Sergeant Grayling accidentally shot and killed a young girl. This causes him to turn to opium, earns him a year in the stockade, and gets him demoted and ReassignedToAntarctica. He treats his transfer as an opportunity to redeem himself.
* ''Film/ThePrivateLifeOfSherlockHolmes'' follows Franchise/SherlockHolmes on a case which he later comes to consider one of his greatest failures.
* Nathan Wallace from ''Film/RepoTheGeneticOpera'' is wracked with guilt over his failure to save his wife, [[MoralityChain Marni]]. It's what caused him to become a Repo Man in the first place.
* Jake Rainer from ''Film/SilentFall'' used to run a group home for autistic children, until a boy under his care committed suicide because Jake pushed him too far in a therapy session. Jake quit working with kids after that.
* ''Film/StarTrekIITheWrathOfKhan'': Kirk's blunder in failing to arm the Enterprise in time resulted in Khan blasting the ship nearly to hell. He came back nicely though...
* In ''Film/StarTrek2009'', Spock-prime's greatest failure was not arriving in time to save the planet Romulus from a supernova blast. This results in a mad man from the future seeking vengeance on The Federation and destroying Spock's home planet, Vulcan.
* ''Franchise/StarWars'':
** There's the stormtrooper in the picture at the top of the page (Those WERE the droids he was looking for). The 2017 book ''Literature/FromACertainPointOfView'' has a story about that stormtrooper, operating number TD-110.
** The gunnery officer on board Darth Vader's ship told the gunner, "Hold your fire, there's no life-forms [on board]" (on the escaping life-pod carrying [=C-3PO=] and [=R2-D2=]); forgetting (a) that droids, not being life-forms, wouldn't show up on a scan for life-forms, and (b) he REALLY should have scanned for droids as well, since the Rebellion has a history of employing droids as agents.
** In ''Film/ReturnOfTheJedi'', when Yoda passes away and becomes one with the Force, he admits his sole regret was not allowing Obi-Wan to tell Luke the truth about his father, understanding from prior consultations with the Force ghost of Qui-Gon Jinn that confessing this regret was the only way he could become one with the Force.
--->'''Luke''': Master Yoda, is Darth Vader my father?\\
'''Yoda''': Rest I need. Yes. Rest.\\
'''Luke''': Yoda, I ''must'' know.\\
'''Yoda''': Your father he is. Told you, didn't he?\\
'''Luke''': Yes.\\
'''Yoda''': Unexpected this is, and unfortunate.\\
'''Luke''': Unfortunate that I know the truth?\\
'''Yoda''': No, unfortunate that you rushed to face him, that incomplete was your training, that not ready for the burden were you. Obi-Wan would have told you long ago, had I let him. Now, a great weakness you carry. Fear for you I do.\\
'''Luke''': I'm sorry.\\
'''Yoda''': Face Vader you must, and "sorry" will not help.
** ''Film/TheLastJedi'' reveals what happened to Luke during the TimeSkip after ''Film/ReturnOfTheJedi''. [[spoiler:Sensing his nephew Ben's dark future, Luke was briefly ready to murder him in his sleep to prevent it from happening. [[MyGodWhatHaveIDone Just as Luke realized what he was doing]], Ben woke up and defended himself. [[SelfFulfillingProphecy As a result]], Ben pledged his loyalty to [[BigBad Snoke]], destroyed Luke's Jedi academy, and [[CreateYourOwnVillain adopted the identity of Kylo Ren]]]].
* The death of Xavier in ''Film/XMenTheLastStand'', which Magneto directly caused by awakening Dark Phoenix.
-->'''Magneto''': Charles Xavier did more for mutants than you'll ever know. My single greatest regret is that he had to die for our dream to live.
* ''Film/Underworld2003'': In the extended cut and novelization of the first film, Michael Corvin had a fiancee named Samantha. They were in a car crash, and because Michael had no idea what he was doing, he was unable to save her from bleeding out. Determined to never let a tragedy like that happen again, Michael became a doctor. At one point, he laments that if he knew then what he knows now, he would have been able to save her.

[[folder:Literature]]
* Jake from ''Literature/{{Animorphs}}'', whenever he recalls the David incident. Also the fact that Jake couldn't save Tobias from being trapped as a hawk. Even moreso, the fact that he couldn't save [[spoiler:Rachel or Tom from dying, not to mention the order to kill seventeen thousand Yeerks. Those two failures become the entire focus of his personality for about five years]].
* ''Literature/TheBartimaeusTrilogy'': Bartimaeus feels the death of his master Ptolemy [[spoiler:in order for Bartimaeus to live]] is this, and his guilt is so bad he wears the face of Ptolemy millennia after the boy's murder.
--> '''Bartimaeus:''' "It's two thousand, one hundred and twenty-nine years since Ptolemy died. He was fourteen. Eight world empires have risen up and fallen away since that day, and I still carry his face."
* ''Literature/{{Beachwalker}}'''s protagonist had one of these in the form of [[spoiler: her mother's death]]. She is determined to keep the past from repeating itself, whatever the cost to herself.
* In Anne [=McCaffery=]'s ''[[Literature/TowerAndTheHive Damia]]'', the title character accidentally fried the mind of [[TheirFirstTime her first lover]]. She considers it this because not only did she never consider keeping her mental guard up while with a far lower [[PowerLevel T-rating]], she ignored Afra's warning to "be careful" out of spite, due to a fight they'd had earlier (After Afra had rebuffed a rather unsubtle attempt at seduction). This helped drive a wedge between herself and Afra that lasted a decade[[note]]Though not only did Afra actually want her, but wanted Damia to see him as himself and not just "Good Ol' family friend Afra", but she thought the whole thing was being driven by her mother, the Rowan.[[/note]] Later books showed that Damia made sure her children knew all about "the facts of life" so they wouldn't go through what she did.
* Near the start of ''Literature/DoctorSleep'' we get a glimpse of Daniel Torrance's adult life, one spent with alcohol and drugs in order to weaken the terrible visions his shining gives him. He eventually reaches the lowest point, however, when he robs a young mother of her money. For the next couple of years, Danny can't forgive himself over this (the visions of the child and mother's deaths don't help), and it causes him to eventually stop drinking and settle in a town for good. [[spoiler:At the end of the book, 15 years later, he eventually decides to come clean and tells his friends about the deed... and is surprised to see that they don't give it much thought (being ex-drunkards like him, they had heard and done things just as bad)]].
* ''Literature/TheDresdenFiles'':
** Harry considers [[spoiler:his lover]]'s half-conversion to a Red Court vampire and his inability to find a cure for her to be his greatest failure, driving him to near-poverty and a long HeroicBSOD shortly after it first happens. Years later, when he [[spoiler:destroys the Red Court at the cost of said lover's life]] and then learns that that act [[spoiler:cured all the other half-turned people]], he says that whatever number of people he saved, it will always be one too few.
** ''Bombshells'' reveals that Molly thinks of [[spoiler:Harry]]'s SuicideByCop this way, because she enabled it. If she'd thought through the consequences of this act, [[spoiler:the Fomor would not have such a stranglehold on Chicago]]. Notably, when [[spoiler:Harry is resurrected]], she becomes fiercely protective of him.
* ''Literature/ForeverGate'': Hoodwink never forgave himself for allowing a rich guy to brainwash his daughter into the ideal HouseWife. It led him to drinking which drove away his wife. Now he throws himself into harm way's way whenever Ari's in danger to make up for it.
* John in ''Literature/TheGrapesOfWrath'' thought his wife had a stomach ache when what she really had was much more serious. He's never forgiven himself, and his every action is driven by a desire to atone.
* From the ''Literature/HarryPotter'' series:
** It's revealed in ''Literature/HarryPotterAndTheDeathlyHallows'' that Dumbledore is wracked with guilt at his failure to [[spoiler:take care of his little sister, whom both of his parents died to protect. He instead chooses to run around with Grindelwald [[FantasticRacism espousing anti-Muggle ideals]]; and she is accidentally killed during a fight they have]]. He learns from the whole thing that he ought not to be trusted with power; and it certainly seems to be his one failure. He straight-up tells Leta Lestrange (who similarly is wracked with self-loathing over [[spoiler: inadvertently causing a sibling’s death]]) in ''Film/FantasticBeastsTheCrimesOfGrindelwald '' that it’s his biggest regret in life.
** It could be argued that Harry's own greatest failure comes in ''Literature/HarryPotterAndTheOrderOfThePhoenix'', when his recklessness ultimately results in [[spoiler:Sirius' death]].
** In ''OOTP'', we get a peek into Snape's "Worst Memory": an incident of bullying against Snape by James Potter and Sirius Black, which culminates in Snape calling Lily Evans a [[FantasticSlur Mudblood]] in anger after she comes to his defense. Later, in ''Deathly Hallows'', we find out ''why'' it's his worst memory: [[spoiler:it ruined his friendship with Lily, the only person he ever loved, and destroyed any chances of him getting together with her. And for even more Snape karma, the person she ultimately ''did'' get together with... was the reformed James Potter, [[TookALevelInKindness who had mellowed out of his bullying tendencies by then, according to Remus Lupin]]]].
** Sirius' own greatest failure: convincing James to let Peter Pettigrew become the Potters' SecretKeeper, not knowing that Peter was a Death Eater.
** Horace Slughorn regards divulging information [[spoiler: about [[SoulJar Horcruxes]] to [[BigBad the then-teenager Tom Riddle Jr., a.k.a. Lord Voldemort]]]] as this, as revealed in ''Literature/HarryPotterAndTheHalfBloodPrince''.
* ''Literature/TheHeroesOfOlympus'':
** The Romans lost their eagle standard in a disastrous campaign in Alaska in the 1980s. They're still sore about it.
** They made up for it with some help.
* Numerous characters, including the titular one from the ''Literature/HonorHarrington'' series, consider the events of Oyster Bay to be this for themselves, as Honor puts it, it was their job to stop things like that, and if they can't, what good are they to their people? To be fair, though, the people who did this had tech that was ''far'' better than even Manticore's, and it was specifically designed for stealth.
* Navidson's greatest failure in ''Literature/HouseOfLeaves'' was his failure to save [[spoiler:Delial]], a little African girl dying of starvation, and taking her picture instead. This would continue to haunt him for years.
* ''Literature/JourneyToChaos'': The death of his first three students has haunted Basilard Bladi for years and defined him as a person ever since.
* ''Literature/LookingForAlaska'''s titular character [[spoiler:blames herself for her mother's death when she was a little kid, as she was too shocked to call an ambulance]]. Later in the novel, most of the principal cast (including the narrator) gets their own greatest failure when [[spoiler:Alaska dies in a drunken car accident halfway through the novel]]. The kicker? [[spoiler:The reason she was driving in the first place was that she realized she forgot it was the day her mother died and was trying to visit her mother's grave]].
* North from ''Literature/OfFearAndFaith''. At first this is just implied to be the case with him, as he tells August he only has a single regret. Later on we see what this regret is during a flashback. [[spoiler: When North was a child, he let his three-year-old sister go outside by herself while he was supposed to be watching her. By the time their parents got home (which was about five or ten minutes later), the girl had disappeared without a trace and was assumed dead, and [[ILetGwenStacyDie North has carried guilt over that mistake ever since then]]]].
* ''Literature/ProphetsHouse'' has Sir Magnus, who lost a critical battle during a war between his patron House and its enemies. He's also TheAtoner.
* Lord Wyldon of ''Literature/ProtectorOfTheSmall'' realizes he's screwed up ''horribly'' as the training master for would-be Tortallan knights when two of them fail the Chamber of the Ordeal in one year [[spoiler:with Joren dying and Vinson being revealed as a rapist]]. One of the jobs of a training master is to make sure unworthy pages shape up or get shipped out before they get ''near'' the Ordeal, and while the squires' knight-masters didn't save them either, Wyldon blames himself for letting themselves run wild as bullies because of the "traditional" hazing. It's compounded when he knows that people will probably speak of Keladry as his greatest student when he spent most of her first two years trying to make her leave, so he resigns his post as training master and goes back to being a regular knight despite Kel trying to persuade him otherwise.
* In the ''Literature/RangersApprentice'' book ''The Lost Stories'', it's revealed that Halt's greatest failure is [[spoiler:accidentally causing Will's mother's death]]. Thankfully, nobody blames him for it.
* In the ''{{Literature/Redwall}}'' novel ''Martin the Warrior'', when [[spoiler:the title character's girlfriend is killed fighting alongside him in battle]] he blames himself and goes into self-imposed exile, setting up the events of ''Mossflower'' to which that book was a prequel.
* Jemidon from ''Secret of the Sixth Magic'' by Creator/LyndonHardy is haunted by the memory of his dead little sister, who wouldn't have died if the gold coin his parents gave him to pay for his test as a would-be thaumatuge had been spent on medicine instead. He failed the test, and both he and his parents blame him for her death [[spoiler:... which is ''insane'', because he was only ten when his folks urged him to get tested, and they're the ones who'd set ambition for one child above the life of another]].
* Twenty years before the events of ''Literature/TheSharingKnife'' books, as he faced the creatures of a powerful [[EldritchAbomination Malice]] during what became known as the Battle of Wolf Ridge; Patrol Leader Dag Wolverine lost all but three of his joint command, his left hand, his ''wife'', and [[ArsonMurderAndJaywalking the ridge in question]] in the space of an hour[[note]](the successful delaying action aspect that facilitated the death of the Malice in question was cold comfort)[[/note]]. Heroic Songs and Epic Poems have been composed since, and Patroller Dag [[TheMaidenNameDebate Redwing]] tends to slip out the back when the younger generation of Lakewalkers start in on them.
* ''Literature/SherlockHolmes'':
** Holmes often dwells on his defeat at the hands of Irene Adler in ''A Scandal In Bohemia'', although [[WorthyOpponent he holds no real grudge against her]]. Ironically, the tale of one of Holmes' greatest failures is what first popularized him. While the first Holmes story was ''A Study in Scarlet'', the character and his world didn't hit the big time until ''A Scandal in Bohemia'' proved to be a runaway success.
** As quoted above, ''The Yellow Face'' is a case where his theory about the cause of certain mysterious events proves to be wrong. Yes, even Sherlock Holmes makes mistakes. Within the work, it's more of a [[DownplayedTrope Downplayed]] example, as the situation resolved itself well (unlike many cases of MyGreatestFailure), and the worst harm was to Holmes' pride.
** Creator/AgathaChristie did a hilarious subversion of the trope, and a very obvious TakeThat against the original Sherlock Holmes example just above. Literature/HerculePoirot, the brilliant if egotist detective, retells, at [[TheWatson Hasting's]] insistence, the story of his only failed case, which had involved a chocolate box. He then tells him to whisper "chocolate box" to him whenever he gets too pompous, adding, "I, who have undoubtedly the finest brain in Europe at present, can afford to be magnanimous." Hastings then immediately says "chocolate box." Poirot doesn't get the joke. At all.
* ''Literature/SisterhoodSeries'' by Creator/FernMichaels: Played with rather strangely with Henry "Hank" Jellicoe. ''Game Over'' indicates that there is one topic that he refuses to discuss, to the point that it is not even stated ''what'' the topic is. ''Deja Vu'' reveals that the topic is his wife Louise. She and her daughter left him and went under Witness Protection a ''long'' time ago, and he, with all his power, has ''never'' been able to find her. However, he had treated her like she didn't exist and was just a servant. He took phone calls on his illegal dealings, and he did it right in front of her! She kept a diary of his dealings that apparently ended up in the hands of the UsefulNotes/{{CIA}}, and he, with all his knowledge, has never been able to confirm the story. He wants to find her... and then kill her for having the nerve to go against him and leave him! Even villains can have a My Greatest Failure.
* ''Literature/SpaceMarineBattles''' Damnos arc has two people with this problem.
** In ''Fall of Damnos'', Scipio keeps flashing back to an attack of Nurglite cultists, when he failed to stop [[spoiler:the daemon from possessing Chaplain Orad, thus holding himself responsible for deaths of two of his squadmates]]. This leads him to become a perfectionist [[UpToEleven by Space Marine standards]], and when more squadmates die to the Necrons he's having trouble accepting it truly isn't his fault this time.
** In ''Veil of Darkness'', Sicarius considers Damnos his greatest failure and is fairly confident that he'll be severely punished for losing the planet. Understandable, considering it's his first time that he ever lost as a Captain.
* ''Franchise/StarWarsLegends'':
** ''Literature/XWingSeries'':
*** Sniper-turned-pilot Myn Donos led the shiny new Talon Squadron into a trap, and only he and his astromech survived, through sheer luck. He's the poster child for HeroicBSOD and [[DefrostingIceQueen Defrosting Ice]] [[ColdSniper Sniper]], blaming himself. Interestingly, while he isn't explicitly blamed by others, his instructor wonders if he is such a bad teacher that he can't teach squadrons the quick thinking and flexibility it takes to survive an ambush.
*** Donos was inducted into Wraith Squadron, known for being populated by people on their LastSecondChance. Another Wraith, Castin Donn, was a slicer in a Rebel cell on Coruscant. When they received the broadcast of the [[Film/ReturnOfTheJedi second Death Star exploding]] and the Emperor dying, he hacked public viewscreens to display it, since there was no way the citizens would see it without the filter of Imperial propaganda otherwise. Crowds went nuts, riots and wild celebrations ran through the streets, and in one plaza a huge statue of the Emperor was torn down... and then the stormtroopers came and fired into the crowd, killing many of them. Castin holds himself at least partially responsible.
*** Dia Passik faces her greatest failure in ''Iron Fist'', where she is forced to shoot [[spoiler:Castin]] during a botched infiltration job. (He was ''probably'' already dead.) She comes out of the experience both disgusted by her seeming failure and frightened of her own ruthlessness. However, her companions and superiors praise her actions, telling her that by [[IDidWhatIHadToDo doing what she had to do]], she saved the rest of the team and their whole operation.
*** Kell Tainer has his problems with anxiety and cowardice during missions in ''Wraith Squadron'', which he considers his own major failing, although he eventually deals with them. Given how much of a DysfunctionJunction the Wraiths are, it's not surprising these are handed out pretty liberally.
** Grand Admiral Thrawn of ''Literature/TheThrawnTrilogy'' pulls off his tactical genius through the psychological insights into alien enemies he gains from studying their art. Just once, he failed to gain any insight--and he keeps the original piece of art to remind him. By the time of the trilogy he thinks he's finally starting to understand... not that it will be any help in the future. He'd had to [[EarthShatteringKaboom destroy the planet]]. Pity.
** Darth Vader is both Emperor Palpatine's greatest triumph ''and'' greatest failure, as he muses upon in ''Literature/DarkLordTheRiseOfDarthVader''. He'd spent years moulding Anakin into the perfect Sith, only to have it all go to waste on Mustafar. He even considers just killing Vader, but decides against it since even in his crippled state Anakin is still obscenely powerful and there's no telling how long he'd have to wait until another strong Force user came along.
*** Should have looked on [[VideoGame/TheForceUnleashed Kashyyyk]].
* ''Literature/TheStormlightArchive'': Dalinar was passed out drunk while his brother fought and lost against an assassin. Years later, he still hasn't forgiven himself. [[spoiler:It's not until the Assassin in White comes for him that he finally forgives himself; he realizes at that time that even if he'd been there to defend Gavilar, Szeth would have killed him without breaking a sweat]].
** Also from Stormlight, Kaladin has a ''lot'' of these. Thanks to his HeroComplex, every time he loses someone, this happens, the first of which being [[spoiler:his little brother Tien, who got killed in front of Kaladin after being sent to the front lines to act as bait]]
* In ''[[Literature/EddieLaCrosse The Sword-Edged Blonde]]'', Eddie is haunted by... well, several things, but the biggest is the time he let his girlfriend (a princess, no less) be attacked and killed by a band of thugs. Most people think his failure was just not being able to protect her, but it turns out his culpability was greater than that — Eddie [[spoiler:was actually the one who escalated the confrontation to violence, out of pride and desire to impress his girlfriend]].
* ''LightNovel/TheUnexploredSummonBloodSign'': Kyousuke is driven to save people because he sees himself as bearing half the responsibility for [[CrapsackWorld the current state of the world]]. The exact reasons for this are outlined in the first book, and further elaborated on the fifth. [[spoiler:In the past, he summoned [[TopGod the White Queen]] into the world, and she fell in love with him at first sight. After interacting with her, he decided to try and use her power to help solve the problems in the world. However, others tried to gain control of the White Queen, enraging her and causing her to kill many people. The loss of so major important leaders resulted in the chaotic state of the present world. On top of that, the White Queen is now driven to make him love her again, [[{{Yandere}} at any cost]]]].
* Dimitri Belikov from ''Literature/VampireAcademy'' feels a lot of guilt over not being able to save his friend, the Zeklos lord he'd been assigned to guard, from a Strigoi attack. It's part of the reason he likes going to mass in the Academy chapel.
* Miles Vorkosigan of the ''Literature/VorkosiganSaga'' became fixated on the death of Sergeant Beatrice at Dagoola IV, [[spoiler:but moved on from this when Ekaterin, who would eventually become his wife, pointed out to him that saving her would have resulted in both their deaths]].

[[folder:Live-Action TV]]
* ''Series/TwentyFour'': Jack's failure to protect [[spoiler:Teri]] from the inherent dangers of his profession.
* On ''Series/{{The 100}}'', it's hard to say ''which'' is Bellamy's greatest failure: letting his sister get discovered by the Ark, indirectly causing the deaths of 300 people, or overlooking a supply of guns and bullets that could have protected his people from the Grounders. They all have a pretty big impact on him and drive his transformation into a more responsible and altruistic character.
* ''Series/{{Angel}}'':
** Wesley Wyndam-Pryce committed his greatest failure when he falsely abducted Angel's only child in order to save both from demise. The prophecy which led Wes to believe this was altered, however, and was never meant to come true.
** Charles Gunn's greatest failure was when he made a deal with Dr. Sparrow to make his legal upgrade permanent in exchange for signing to release an ancient curio stuck in customs. This results in the death of [[spoiler:Fred]] and the resurrection of the demon Illyria. Gunn becomes so guilt-ridden that he offers to take Lindsey's place in a hell dimension to get information to stop the Senior Partners.
** Allen Francis Doyle refusing to lend aid to a group of pacifist Brachen demons who were trying to escape The Scourge. Later that night, Doyle experienced his very first vision — that of the entire Brachen clan being slaughtered.
* ''Series/BabylonFive'':
** Delenn's greatest ''self-recognized'' failure was [[spoiler: ordering the complete annihilation of the entire human race over an accident that killed her teacher]]. Despite what they claim, Minbari are extremely compulsive and bloodthirsty.
** Londo Mollari had two greatest failures:
*** [[spoiler: Giving a family heirloom to his mistress (the only person he ever really loved) to wear, making her an easy target for Morden to find and murder]].
*** Getting involved with Morden and his "associates" in the first place, thus kick-starting the entire Shadow war. Londo's life was one long string of incredibly bad choices, motivated by self-interest and fear. By the time he discovered he was on the wrong path and began walking the right path, it was far too late for him to save himself.
** G'kar had at least one greatest failure: Torturing Londo and submitting him to literal MindRape to discover how completely Londo fistfucked the Narn people with the Shadows' help. It took Kosh's intervention to show G'kar that he would eventually fall as low as Londo had, before setting G'kar back [[HeelFaceTurn on the path to redemption]].
** The Soul Hunter in the first season was tasked with retrieving the soul of Dukhat when he was killed during the first contact with Earth, but the Minbari prevented him from accomplishing that, which damaged his already fragile state of mind. After that, he decided he would no longer wait for death, he would simply take worthy souls by force.
* ''Series/TheBoys2019'': Dr. Vogelbaum thinks of Homelander as this for him, saying he should have raised him with affection, not like a test subject in his lab, so that he might have been different.
* ''Series/ElCaso'': Policeman-turned-journalist Jesús Expósito never caught the man who murdered his girlfriend and other four girls, which still haunts him.
* ''Series/DoctorWho'':
** The Doctor felt great guilt over not having the guts to assassinate Davros, creator of the Daleks, when he had the chance. He also tends to feel this whenever he ''fails'' to stop the Daleks, since [[JokerImmunity they always come back]].
** [[spoiler:Adric's death.]] Really, the loss of ''any'' companion usually wound the Doctor deeply and has them beating themselves up for a good while afterwards.
** He's also convinced that he ruins his companions' lives. When the TARDIS voice interface takes his form in [[Recap/DoctorWhoS32E8LetsKillHitler "Let's Kill Hitler"]], he tells it to "give me someone I like." Holograms of Rose, Martha, and Donna are met with a response of "guilt", "also guilt", and "more guilt." He finally settles on the image of little Amelia, "before everything went wrong."
** In between the original and new series, the Time Lords and Daleks fought a war that annihilated both sides. The Doctor's greatest failure is letting his people die and [[SurvivorGuilt surviving]] [[LastOfHisKind himself]].
*** It is revealed in [[Recap/DoctorWhoS30E17E18TheEndOfTime "The End of Time"]], the Tenth Doctor's GrandFinale, that the Doctor really had no choice whatsoever. [[spoiler:The war had brought out the worst in the Time Lords and had made them into {{Omnicidal Maniac}}s as bad as the Daleks, and they were going to destroy all of time and space while cheating death by [[AscendToAHigherPlaneOfExistence becoming beings of pure consciousness]]. So the Doctor chose to lock them and the Daleks and everything else involved in the war outside of normal time and space where they would annihilate themselves while keeping the universe safe.]]
** In the Series 7 finale, [[Recap/DoctorWhoS33E13TheNameOfTheDoctor "The Name of the Doctor"]], it is revealed that [[spoiler: a previously unknown regeneration of the Doctor committed an act so heinous that it went against everything the Doctor stands for. The act was so horrible that the other regenerations ''refuse to even acknowledge his existence'' and he isn't believed to be worthy of the name Doctor. ''However'', this same "Doctor" claims IDidWhatIHadToDo, "without choice, in the name of peace and sanity." Eleven counters "But not in the name of the Doctor." The 50th Anniversary special, "The Day of the Doctor" revealed the act in question was this regeneration of the Doctor was the one who ended the aforementioned Time War]].
--->'''The Doctor:''' My name — my ''real'' name — that is not the point. The name I chose is the Doctor. It's like a promise you make. [[spoiler:He's the one who broke the promise.]]
** After the 50th-anniversary special [[spoiler:has him '''''saving''''' Gallifrey in the war, rather than destroying it]], the Doctor believes he's "achieved" this in both the opening and closing stories of Series 9. In [[Recap/DoctorWHoS35E1TheMagiciansApprentice "The Magician's Apprentice"]]/[[Recap/DoctorWhoS35E2TheWitchsFamiliar "The Witch's Familiar"]], he comes to believe he is responsible for [[spoiler:setting Davros on the path that led him to create the Daleks]], but in fact [[spoiler:he's actually the reason Daleks understand the idea of mercy]]. In [[Recap/DoctorWhoS35E10FaceTheRaven "Face the Raven"]]/[[Recap/DoctorWhoS35E11HeavenSent "Heaven Sent"]]/[[Recap/DoctorWHoS35E12HellBent "Hell Bent"]], he blames himself for Clara [[spoiler:being KilledOffForReal in a SenselessSacrifice]] due to his "bad", unchecked influence on her tragically dovetailing with the fallout of several recent choices he's made. This temporarily turns him into a WoobieDestroyerOfWorlds, almost ''destroying all of space and time'' in an attempt to undo this tragedy. His return to sanity requires realizing that, among other things, it isn't his fault and thus '''''not''''' an example of this trope.
* One of the defining moments for ''{{Series/Firefly}}'s'' lead character, Malcolm Reynolds, was the complete, total, and utter defeat he suffered at the Battle of Serenity Valley. By the time the battle was over, he had lost his faith and had been turned from a chipper, patriotic, and energetic soldier into the tired, cynical bastard he is in the series.
* Henry Morgan of ''Series/{{Forever}}'' planned to free slaves on a slave transport ship when he was shot and killed ([[ResurrectiveImmortality he got better]]) before fully carrying it out. The ship was subsequently lost at sea and he believes that his immortality is a punishment for his responsibility in the deaths of those three-hundred people. [[spoiler: He later meets a descendant of one of the slaves: turns out that, upon being shot, he had dropped the key to the slave pen within reach of one of the slaves, enabling them to rise up, take the ship, and sail it to North America where they could live as free people]]. Also, Henry abandons medicine after [[spoiler:he makes the choice to run away instead of trying to save a man who has been shot, as he himself has been shot and is dying. He chooses his own safety (i.e. so no one sees him die and vanish) over a man's life, thus violating the oath he took as a doctor. He never forgives himself for this and doesn't believe he's worthy of being one]].
* Sandra from ''Series/ForThePeople'' sees her loss in the Pilot this, as she failed to protect a young man from being found guilty of terrorism even though he was clearly a victim of entrapment.
* ''Series/GameOfThrones'':
** For Catelyn Stark, it was saving Littlefinger from Brandon Stark, though it's downplayed as she never does find out how instrumental Littlefinger was in instigating [[spoiler: Ned's death.]]
** Davos's reaction to his son's death in the wildfire explosion at Blackwater has shades of this trope.
** Brienne perceives her failure to protect Renly from a magical HumanoidAbomination as this.
** Jon Snow does not take his inability to save all the Wildlings at Hardhome well, not at ''all''.
** The almost total destruction of the Targaryan dynasty under Barristan's watch drives him to seek redemption by serving Daenerys.
* In ''Series/HerculesTheLegendaryJourneys'', the first episode had Hera murder Herc's wife and children. While Hercules initially lashes out by destroying Hera's temples and turns away a man looking for his help against the She-Demon, he eventually realizes that revenge isn't the answer. (The episode wasn't titled "The Wrong Path" for nothing.) After killing the She-Demon and saving her victims, Hercules vows to honor his family's memory by WalkingTheEarth and performing heroic deeds.
* In ''Series/HomicideLifeOnTheStreet'', Detective Bayliss is haunted by his failure to solve his very first case, the murder of a little girl called Adena Watson. Although he makes numerous efforts to put it behind him, and later develops from the rookie he was when he caught the case to a competent, seasoned homicide investigator, his obsession persists throughout the entire series, even after it seems that the girl's family have moved on.\\
\\
The case is based on the real-life unsolved murder of Latonya Kim Wallace, the "Angel of Reservoir Hill", the investigation into which is covered in the book upon which the series is based. As noted in the book, the real-life detective in charge of the investigation grew fixated on the case, but the epilogue stated that at the time of writing he was beginning to accept it and move on.
* ''Series/{{House}}'': House declines to fire Thirteen after a careless mistake resulted in a patient's death, knowing that it would be this trope for her, and she would be that much more careful.
* ''Series/{{JAG}}'': For Admiral Chegwidden it is not having been with his daughter Francesca (who grew up in Italy with her mother and stepfather), during her childhood and adolescence.
* Characters motivated by this do occasionally pop up in ''Franchise/KamenRider''.
** ''Series/KamenRiderDouble'': Shotaro Hidari blames himself for the death of his boss, Sokichi Narumi, primarily because he ignored Sokichi's orders on a particularly dangerous job, which lead to guards chasing them and gunning Sokichi down. As a result of this and Sokichi's FamousLastWords, Shotaro lives his life trying to achieve the "hard-boiled detective" ideal his boss embodied.
** ''Series/KamenRiderGaim'': Once he finds out about it, [[spoiler:killing Yuuya]] is this for Kouta. Likewise, his buddy Mitsuzane treats [[spoiler:his ChronicBackstabbingDisorder]] as this when he finds out that trusting the wrong people while hurting the ones who would legit help him ended up with [[spoiler:Mai and Kouta being killed by his actions, indirectly ''and'' directly]]. They both became TheAtoner and it would take a while for them to get over it.
** ''Series/KamenRiderDrive:'' Shinnosuke feels like he is to blame for the GameBreakingInjury of his partner as he accidentally shot at a gas valve that blew up and wound up hurting his partner. It's made worse because around that time, the entire world was going through a [[TimeStandsStill global slow down]], so he got to see everything unfold in slow motion, [[AndIMustScream unable to do anything but watch]].
** ''Series/KamenRiderExAid'': Failure to save a patient suffering from [[EverythingFades Game]] [[TheVirus Disease]] haunts Hiiro Kagami and Taiga Hanaya for most of the story. The former blames himself for causing her infection and the latter for not treating it in time. Moving on required them to understand and stop blaming both themselves and each other.
* In ''Series/{{Leverage}}'', Nate Ford's son died because the insurance company he worked for refused to pay for lifesaving treatment. And, just to [[KickTheDog twist the knife]], when he [[StartOfDarkness turns to crime]] he becomes a multi-millionaire almost immediately.
* ''Series/TheMentalist''[='=]s Patrick Jane taunted serial killer Red John on live TV. Red John retaliated by murdering the two most important people in his life; his wife and daughter. Although he rarely speaks of it, it's clear when he does that this tortures him daily.
* The title character of ''Series/{{Merlin|2008}}'' is an IronWoobie turned UpToEleven. But when he fails to heal the king and quite possibly turns Arthur away from magic forever, he very nearly crosses the DespairEventHorizon and only stops because he's reminded that Arthur will need his support as king.
* Detective ''Series/{{Monk}}'' has solved every case he has come across. However, he's been stuck for a long time on that little case of his wife Trudy being blown up by a car bomb. He also blames himself, as he believes it was him being a police detective that made her a target. [[spoiler:In fact, her murder had nothing to do with him and everything to do with a daughter she had out of wedlock with an influential judge before meeting Monk, who was running for a higher office and wanted to remove any trace of his infidelity. The worst thing is, Monk had the answer all this time in the form of a videotape that his wife left him as a gift, except he couldn't bring himself to open the gift until the series finale]].
* ''Series/MotherlandFortSalem'': Bridey is haunted by her inability to save her sister from a deadly attack.
* Rumplestiltskin in ''Series/OnceUponATime'' only broke one promise, the one he made with [[spoiler: his son Baelfire]]. He was given the chance to [[spoiler: live with his son in another world without magic to free him from the power of the Dark One]], but was unable to [[spoiler: let go of his power and lost his son as a result]]. He set out making the Dark Curse so he could find a way to fix this.
** Jiminy Cricket saw what happened to [[spoiler: Geppetto's parents]] as this for him. He sets himself as TheAtoner to repent.
* ''Series/ParksAndRecreation'': A rare example from a comedy series, Ben Wyatt bankrupted his hometown when he was elected mayor at age 18. In present-day he's incredibly cynical, cautious, and spent his career working as a state auditor to make up for his past mistakes and save other towns from collapsing like his did. At one point he openly admits to Leslie that the event ruined his life and he'd love to run for office again someday but has to prove he's responsible now. With Leslie's help he gradually moves past it, but his hometown still hates him and the media frequently rip him apart over the debacle.
* ''Series/PersonOfInterest'':
** Finch was the first person to deem the Numbers as irrelevant in the grand scheme. When he discovered [[spoiler:Nathan had started trying to help them, Finch shut down the backdoor he was using. The next day Nathan was killed and Finch was horrified to discover Nathan had been listed as a Number]]. This was what convinced him to protect the Numbers and led him to Reese.
** Reese broke up with his girlfriend Jessica when he decided to reenlist following 9/11. Years later he has become a government assassin while Jessica married a man who turned out to be violently abusive. She calls Reese for help and he tells her that he will come as soon as he can. Unfortunately, right after the phone call he is sent on a mission to China and by the time he gets back to the US, the ex-girlfriend has been murdered by the abusive husband. Reese gets revenge on the husband and then reaches a DespairEventHorizon and becomes a homeless bum on the streets of New York. Finch finds him there and offers to save people in situations like the one that killed Jessica.
* ''Franchise/PowerRangers'':
** ''Series/MightyMorphinPowerRangers'': Failing to retrieve the Green Candle in season one, thus saving Tommy from losing his powers, was shown to have haunted Jason for a long time, to the point where he even makes reference to it in ''Zeo''.
** [[Series/PowerRangersInSpace Andros]]. [[HurtingHero Dear Lord, Andros]]. First, he loses his sister as a child [[spoiler:and she grows up to become one of the {{Big Bad}}s]], then his best friend Zhane is nearly killed during a battle and Andros puts him in cryogenic stasis to keep him alive. [[spoiler:They both get better]].
* ''Series/{{School|2013}}'':
** Go Namsoon [[spoiler: he breaks his former best friend Heungsoo's leg, while he and the rest of his gang were beating Heungsoo up as part of the process and punishment for him leaving. Heungsoo had been told by his coach that if he had serious aspirations of playing football professionally he couldn't be part of the gang any longer, but this injury meant he could no longer play]]. After this Namsoon experiences HeroicBSOD and spends a year eating, sleeping and crying.
** Kang Sechan [[spoiler: His student commits suicide because he doesn't set aside the time to talk to her when he comes to him]]. This causes him to give up teaching in school for fear of failing another student.
* The ''Series/{{Sherlock}}'' episode "The Six Thatchers" ends [[spoiler: with a take on "Norbury", but instead of the location where he made a stupid mistake that ultimately didn't matter, it's the name of the criminal he allowed to kill Mary Watson because he was showing off]].
* ''Series/{{Sliders}}'':
** Arturo considered his work on traveling to parallel universes his greatest failure until Quinn Mallory discovered how to do it.
** Quinn himself for the group's travels. In the PilotMovie, he wanted to show off his discovery to Wade and Arturo, but he didn't fully understand it. He accidentally uses too much power, which causes the vortex to suck in the three of them and Rembrandt (who was just driving by). On the next world, they're forced to slide early, which erases their home Earth's coordinates and leaves them lost in the multiverse. Quinn can only blame himself and is determined to get the others home no matter what. His guilt is compounded in Season 3 when Arturo is killed TakingTheBullet for him.
* In ''Series/{{Smallville}}'', [[{{Superman}} Clark Kent]] has had several, including when he reversed time (a one-use-only deal) to save Lana's life, only for his dad to suffer a heart attack and die at the end of the day. Also, John Corben/Metallo blames him for his turn to evil, because when Clark saved a bus from crashing, a passenger from that bus went on and murdered Corben's sister the next day. But in his opinion, his greatest failure is probably in the season eight finale [[spoiler:when a complex chain of actions lead to the death of Jimmy]].
* ''Series/TheSpy'': Israeli spymaster Dan Peleg has never gotten over allowing an extremely talented field agent to get assigned to deep cover because he knew the man was too eager to please and would take excessive risks. The agent was almost immediately captured and killed. Peleg is motivated to not let history repeat itself when dealing with a similarly enthusiastic Eli Cohen.
* ''Franchise/{{Stargate|Verse}}'':
** ''Series/StargateSG1'':
*** Lt. Col. Cameron Mitchell's is when he bombed a truck he thought was carrying enemy soldiers, but was instead carrying civilians.
*** Jack O'Neill's is the fact that his son shot himself with Jack's gun.
** ''Series/StargateAtlantis''. Rodney [=McKay's=] unintended destruction of a solar system (well, five-sixths) is brought up occasionally by Sheppard, though usually as a joke, seeing as the system was uninhabited.
* ''Series/StarTrekTheOriginalSeries'':
** Captain Kirk failed to restrain his friend Commander Mitchell when he began exhibiting God-like powers, although he was warned by Mr. Spock. It wasn't until Mitchell killed a crewman and set about destroying the Enterprise that Kirk took action.
** And prior to that, he was haunted for over a decade by the deaths of over 200 crewmen (including his CO) because he thought his hesitation in firing on the MonsterOfTheWeek allowed it to attack. It was only when he saw it would have made no difference that he accepted his choice.
** Beyond Kirk, Commodore Decker in "The Doomsday Machine" is pushed beyond the DespairEventHorizon when he watches in horror as the planetoid he evacuated his crew to is destroyed by the titular device, killing everyone. He's DrivenToSuicide by the result.
* ''Series/StarTrekTheNextGeneration'':
** Subverted in the episode "Tapestry", where what Picard thought was his worst failure was picking a fight as a cadet and getting an artificial heart due to getting his real one stabbed. As Q showed, that incident made Picard what he is.
** In "The Bonding" the non-corporeal Koinonians chose not to interfere when their physical counterparts began a war that ultimately destroyed them. They view their failure to prevent this as a great shame.
** In "Family", Picard perceives being unable to stop the Borg from using him as part of their invasion in "The Best of Both Worlds" as his greatest failure.
** Lwaxana Troi is shown to be going to great lengths to cover up what she sees as her greatest failure in the episode "Dark Page." [[spoiler: She blames herself for the accidental drowning of her first-born daughter & Deanna's older sister]].
* ''Series/StarTrekDeepSpaceNine''
** In the episode "Things Past", Odo's friends witness his greatest failing as a security officer during the Cardassian occupation of Bajor: in the interest of keeping order, he condemned three innocent Bajorans for attempting to assassinate Gul Dukat based on circumstantial evidence. He eventually recognized his mistake and has tried to do better ever since.
*** At some points, he seems to suggest that working for the Cardassians in general was this to him.
** Worf has his own: as a child, not realizing how much more powerful Klingons are than humans, he killed another child during a game of soccer. He's held himself back from full enthusiasm over anything ever since.
* ''Series/StarTrekVoyager'': Chakotay failed to catch (and ended up falling in love with) the Cardassian spy Seska in his Maquis cell, which came back to haunt him when she betrayed the series' titular ship and its crew to the evil Kazon. To add insult to injury, he also failed to catch the ''Federation'' spy Tuvok, compounding the guilt over Seska's betrayal. He only (sorta) recovered when he realized that ''neither'' spy realized the other was in the cell, making the incident not (entirely) his fault.
-->'''Chakotay''' (to Tuvok): "She was working for them, you were working for her... was ''anyone'' on my ship working for ''me???''"
* ''Series/StarTrekPicard'': Hugh is responsible for the well-being of the former Borg drones on the Artifact, so when about a dozen of them are gunned down by Narissa and her guards, he feels guilty that he was unable to shield them from the cruelty of the Romulan Free State.
-->'''Hugh''': I've failed them all.
* ''Franchise/SuperSentai'':
*** ''Series/HyakujuuSentaiGaoranger vs Super Sentai'' has one given for 4 of the 5 returning heroes, told in order to motivate the Gaorangers back to form.
** ''Series/GoGoSentaiBoukenger'': Satoru Akashi has the time his friends died in a cave-in, never once losing faith that he would save them.
** Similar to the aforementioned''Manga/OnePiece'', some of the heroes in ''Series/KaizokuSentaiGokaiger'' have this.
*** Captain Marvelous has his failure to prevent [[EvilCounterpart Basco]] from dismantling the Red Pirates from within, leading to the [[spoiler: (apparent)]] death of [[BigGood AkaRed]].
*** Joe Gibken has the fact that his best friend was captured and ReforgedIntoAMinion on his mind for most of the series. [[spoiler: He gets over it after a conversation with [[Series/ChoujuuSentaiLiveman Yellow Lion]], who went through a similar experience.]]
* ''Series/{{Supernatural}}'':
** Dean is unable to keep Sam safe and protected, with Sam eventually being killed. Dean then breaks the first seal, which ultimately leads to the apocalypse.
** Sam fails to save Jessica. Later he drinks demon blood and allows himself to be manipulated by Ruby, which leads to the breaking of the last seal, the start of the apocalypse, and the release of Lucifer. In Season 8, Sam fails to close the Gates of Hell.
** Castiel kills thousands of his brethren and assumes to role of God after consuming the souls of purgatory. He later is manipulated by Metatron to banish all the angels from heaven.
* ''Series/{{Torchwood}}''. Jack's inability to [[spoiler:find (or redeem) Grey]].
** Jack. [[spoiler:"Day Four" with Ianto's death]]. This, in combination with [[spoiler:his decision in "Day Five" to save the day by killing his grandson (although this doesn't count as a failure, despite [[TearJerker how tragic it was]])]] was enough to convince him that [[spoiler:he had to completely leave the Earth, despite Gwen's best efforts]].
* ''Series/TheTwilightZone1959'': In "[[Recap/TheTwilightZoneS3E67TheArrival The Arrival]]", the disappearance of Flight 107 is the only case that the FAA investigator Grant Sheckly was never able to solve in 22 years on the job. He was so [[TraumaInducedAmnesia traumatized by his failure that he repressed his memory of the case]].
* ''Series/TheTwilightZone2002'': In "Azoth the Avenger is a Friend of Mine", the title character reveals that in his youth, he fled a demonic attack that killed his whole family. His shame over his action continues to motivate him.
* ''Franchise/UltraSeries''
** ''Series/UltramanMebius'': Ultraman Hikari's failure to protect the planet Aarb from [[VillainousGlutton Bogal]], which was what drove him to become the vengeance-hungry warrior Hunter Knight Tsurugi.
*** Mebius has one connected to his human form, Mirai. [[spoiler:When he first arrived at Earth, he spotted a spaceship being sucked into a wormhole, but failed to get the ship and its pilot out before the wormhole closed. Thus, [[DeadPersonImpersonation he chooses to take on the form of the pilot]] to give himself a reason to improve as a hero.]]
** ''Series/UltramanX'': The title hero's failure was causing the Ultra Flare incident by [[HurlItIntoTheSun throwing]] [[spoiler:Greeza]] [[HurlItIntoTheSun into the Sun]] at the start of the series, since it caused giant monsters to appear all over Earth, creating worldwide destruction and costing the lives of his human host Daichi's parents.
* In the UK version of ''Series/TheVoice'', [[Music/TheBlackEyedPeas Will.i.am.]] (one of the coaches for the UK series) called himself an idiot for not hitting his button during seventeen-year-old self-trained opera prodigy Shansel Husayin's note-perfect performance of "Nessum Dorma", and profusely apologized to her for not doing so, stating that he realized too late that she was an opportunity to "reinvent pop radio." As late as a mid-2013 interview, he's apparently ''still'' kicking himself in the butt for letting her slip through his fingers.
* In ''Series/{{Warehouse 13}}'', Myka is wracked with guilt over the death of her partner and lover, while she was in charge of the mission. For Pete, it's the death of his firefighter dad in the line of duty, when Pete decided not to tell him that he had one of his bad feelings. One episode serves to get both characters to come to terms with their respective guilts and realize they're not at fault. Myka's partner disobeyed her orders and got himself killed, while Pete's dad would've done his job no matter what his son said. Everything H.G. Wells does is because of the death of her daughter during a home invasion a century ago, while she was out of town.
* ''Series/TheXFiles'': Fox Mulder is plagued by guilt over not protecting his younger sister, Samantha, from [[AlienAbduction abduction]] when they were children, despite the fact that it involved circumstances well beyond his control. His parents don't help assuage his guilt over it; at one point a clone claiming to be his sister is killed, and his father is upset and tells Mulder that ''he'' has to tell his mother that he lost his sister... again. As a result, he becomes obsessed with protecting Scully, especially after her abduction in season two. He ditches her several times, to her annoyance, and at times demands she stay out of a case for fear of her life. And woe is you if you're the one [[BerserkButton who hurts Scully]].

[[folder:Podcasts]]
* Taako of ''Podcast/TheAdventureZoneBalance'' [[spoiler: screwed up a transmutation spell during his cooking show that resulted in everyone who ate the samples of what he made getting poisoned and dying on the spot. Retroactively subverted when he learns, years later, that his jealous roadie Sazed had actually poisoned the food with arsenic.]]
** Magnus also [[spoiler: deeply regrets his failure to protect Raven's Roost from Governor Kalen.]]
** Lucretia sees [[spoiler: her time in Wonderland]] as this.

[[folder:Roleplay]]
* ''RolePlay/YuGiOhEastAcademy'': While he tries to deny it, Marcus clearly feels horrible about [[spoiler: the death of Sylvestre]].
* In ''Roleplay/SurvivalOfTheFittest'', Adam Dodd doesn't only have one of these, but two. The first of these is allowing himself to become separated from the other members of his group - among them his girlfriend and other close buddies of his. [[spoiler:They all proceed to be killed, and in one case, raped]]. Adam blames himself for this. His second stems from an incident where his (mentally unstable) brother attacked him. Adam regrets throughout version 1 his failure to forgive his older brother [[spoiler:until one of the very last scenes of the V1 endgame]].

[[folder:Tabletop Games]]
* In ''TabletopGame/{{Exalted}}'', this is how Green Sun Princes become Green Sun Princes. They're on the edge of a heroic, epic act that would grant them Solar Exaltation... but then they choke, and then, in their moment of weakness, despair, and regret, the [[EldritchAbomination Yozis]] are there to offer them the DealWithTheDevil that grants them the Infernal Exaltation.
* For decades in ''TabletopGame/ForgottenRealms'', [[Literature/TheLegendOfDrizzt Drizzt Do'Urden]] had kept a vow to [[ApeShallNeverKillApe never kill another dark elf]]. However, he couldn't keep it forever, and in order to escape, he had to kill one of his kin. He was guilt-wracked for this... but, in a possible subversion, not for long, as he realized it was a hypocritical vow, given that he had often seen the necessity of killing orcs, humans, goblins, duergar, wererats, and others who actually tended to be less AlwaysChaoticEvil than his own people. In addition, the primary reason he had been able to keep that vow for so long was that he had been able to ''avoid'' other members of his race for most of that time, and being able to keep a vow because you never end up in a situation where breaking it is possible doesn't mean all that much.
* In the ''TabletopGame/{{Warhammer 40000}}'' universe, the vast Imperium of Man has its own greatest failure during the end of the Great Crusade. During the beginning, it was believed that there was nothing science and reason couldn't conquer. [[EldritchAbomination And then they met Chaos...]]. Horus rebelled, the Emperor was placed upon the Golden Throne, and suddenly the Imperium became very suspicious of itself. [[KillItWithFire So new measures were taken to make sure such heresy never happened again]].
** Another 40K example is Sarpedon of the Soul Drinkers, who nearly led his Chapter into the clutches of the Dark Gods... and has ''eight legs'' to remind him of the danger of Chaos.
** This is nothing compared to the Eldar race's greatest failure, which resulted in: 1) the destruction of their galaxy-spanning empire and the deaths of billions (if not ''trillions'') of their race; 2) the fragmenting of the race into [[TheStoic repressed ivory-tower ascetics]], [[NatureHero nature-attuned tribal agrarians]], and [[AxeCrazy blood-thirsty torture-obsessed sociopaths]]; and 3) '''the creation of one of the most powerful, and [[{{Squick}} seriously messed-up]] Chaos gods'''.
** [[EvilSorcerer Ahzek]] [[TheArchmage Ahriman]] feels a lot of guilt for accidentally transforming most of the Literature/ThousandSons into suits of AnimatedArmor when he cast the Rubric and spends a lot of time trying to restore their humanity. The novel ''Ahriman: Unchanged'' reveals that he’s repressing an even deeper sense of guilt for failing to save his brother Ohrmuzd from dying of the [[BodyHorror flesh-change]].
[[/folder]]

[[folder:Theatre]]
* In the ''Theatre/MrsHawking'' play series: In part four, ''Gilded Cages'', it is suggested that for Mrs. Hawking this is [[spoiler: her very first attempt at superheroing, when she tried to help her maid Malaika steal food for her starving village in Singapore. Their attempts resulted in failure, Malaika losing her job and imprisoned, and herself forced to marry in exchange for her father providing relief to the village.]]
[[/folder]]

[[folder:Toys]]
* Lesovikk in Toys/{{Bionicle}} once briefly hesitated in a fight against a group of Zyglak, costing him his entire Toa Team, and driving him into a millennia-spanning HeroicBSOD and WalkingTheEarth for ages.
[[/folder]]

[[folder:Video Games]]
* Pick a Creator/BioWare game, and chances are you'll hear one of these from at least one of your party members. Chances are, you'll end up with them when they attempt to correct said failures, too. A more comprehensive list:
** In ''Franchise/MassEffect'', Garrus was rather angry about an organ farmer that C-Sec's regulations prevented him from stopping. His personal mission in that game is to hunt down and kill the organ farmer.
*** In ''VideoGame/MassEffect2'', you recruit Garrus from the battlefield in which most of his team was slaughtered. His loyalty mission is to hunt down the man that sold them out.
** Also in ''VideoGame/MassEffect2'' is Thane's regret that he left his son behind following his vengeance on his wife's murderers. His loyalty mission is to keep Kolyat, the son in question, from following in his footsteps.
** While Samara cannot be blamed for having daughters who are Ardat-Yakshi, Asari with a rare genetic disease that makes them addicted to murdering people by draining their life energy, she later makes it her life's mission to hunt down and destroy Morinth, the daughter who ran to preserve her freedom rather than join her sisters in isolation at a remote monastery where they learn to suppress their urges and are far removed from any temptations.
** In ''VideoGame/MassEffect3'', being forced to leave Earth in the midst of a Reaper invasion is this for Shepard [[spoiler:until the fall of Thessia where s/he hits his/her lowest point, blaming him/herself for not getting the right info and for the fall of the asari homeworld]].
** In the same game, [[spoiler: if Shepard tries to convince Mordin to fake curing the genophage, Mordin will finally break down and confess that he views his works to negate the slow krogan development of immunity to it as this. He spent the previous game and his earlier interactions in this one denying that he felt any guilt over it, though]].
** Joker reveals in ''3'' that he considers the destruction of the original Normandy to be his. Not the destruction itself, but his initial refusal to leave the doomed ship directly resulted in Shepard's original death. He has never quite gotten the guilt from it and, after Shepard's resuscitation, goes above and beyond to keep the Commander both physically and mentally safe to make up for it.
** In ''VideoGame/JadeEmpire'', [[TheAtoner Sagacious Zu]] regrets his failure to save Master Li's family from the Emperor's vengeance. You learn later that [[spoiler: Master Li's daughter is still alive, and she happens to be right in your party]].
** In ''VideoGame/DragonAgeOrigins'', Wynne was assigned to mentor a young elven mage during her younger days, and he ended up fleeing the Circle and getting killed by the Templars. [[spoiler: In her personal quest you learn that he actually escaped and Wynne was told he had died to mess with her, and the two get to meet again]].
** Sten considers losing his sword to be his greatest failure. Swords are [[SeriousBusiness very important]] to the Qunari.
** Oghren also blames himself for his entire clan dying and his wife Branka going insane, believing that had he been a better husband she may have not gone on her mad quest for the Anvil of the Void and dragged their clan into their gruesome fate.
** In ''VideoGame/DragonAgeInquisition'', Thom Rainier ordered his men to assassinate a rival Lord. He realized that the target's wife and children were present when he heard the children singing, but didn't call off the attack, resulting in the entire family being killed. He then let his men take the fall and fled. Eventually, [[spoiler:he was recruited for the Wardens by a Warden named Blackwall, [[DeadPersonImpersonation whose identity Rainier assumed after Blackwall died saving him]]]].
** In ''VideoGame/KnightsOfTheOldRepublic'', Carth considers his failure to stop Admiral Karath from turning on the Republic to be his greatest failure; about three-quarters of the way through the game he gets to kill the Admiral.
** In ''VideoGame/NeverwinterNights'', the confused angsty mess of a person that is Aribeth considers her fiancee's unjustified execution at the end of chapter 1 to be her failure.
* ''Franchise/AceAttorney'':
** [[spoiler: Godot/Diego Armando]] projects this onto Phoenix Wright in ''Trials and Tribulations'', feeling that [[spoiler: the death of Mia]] is ''Phoenix's'' greatest failure. It's a cover for blaming himself.
** Detective Badd of ''Investigations'' wears a [[BadassLongcoat bullet-riddled trenchcoat]] to remind himself of his failure to protect Cece Yew from being murdered by a smuggling ring before she could testify. This also led him to [[spoiler: become part of the Yatagarasu]].
* According to [[http://shop.nationalgeographic.com/ngs/product/books/kids-books-and-atlases/animals-and-nature/national-geographic-angry-birds this]] ''VideoGame/AngryBirds'' book by Magazine/NationalGeographic, the [[SmartBomb Mighty Eagle]]'s backstory was that he went into a self-imposed exile after letting the pigs steal the eggs under his watch. His only friends who visit him regularly are the Blues, who feed him cans of sardines and have him tell them stories.
* ''VideoGame/BravelyDefault'': [[spoiler: Ringabel remembers his greatest failure once he regains all his memories... In truth, he is an Alternis Dim from another world, and he failed to save his world's Edea from the true villain Airy. When said villain calls him out on his inability to act in the face of her power back then, the former dark knight cannot defend himself. However, in the credits of the GoldenEnding, Ringabel gets the chance to SetRightWhatOnceWentWrong, proudly proclaiming his original name as he defends Edea]].
* Sarge, from ''VideoGame/ChibiRobo'', blames himself for the loss of Memphis, one of his subordinates. After some of his men abandon the group, and you give him Memphis's dog tags, his [[DrillSergeantNasty tough act comes to a head]], and he loses it. [[spoiler:"YOU'RE NOT FIT TO BE FREE RANGERS! ... And I'm not fit to lead you..." But tears of sorrow quickly turn to tears of triumph as his remaining men come to his aid. "YOU'RE HARD BOILED!"]]
* The beginning of ''VideoGame/TheCloserGameOfTheYearEdition'' has the titular character give up a home run to Carlos "The Machine" Rodriguez near the tail end of Game 6 of the World Series, dashing the New York Yankees' hopes of securing the championship trophy before Game 7 could exist (they were in the lead 3-2 before the incident). This weighs heavily on the Closer, and the rest of the game is an epic journey to redeem his image and expand his pitching repertoire in what little time he has before the final game.
* Deckard Cain of the ''VideoGame/{{Diablo}}'' series has much to regret, as shown in his dialogue in ''VideoGame/DiabloIII'':
-->'''Deckard Cain:''' I am the last of the Horadrim. I couldn't always claim this. In fact, if I had turned to the Horadric teachings sooner, Diablo could have been stopped before his reign of terror began.
-->'''Player:''' You cannot believe this.
-->'''Deckard Cain:''' When the first signs appeared, I did nothing. I had shrugged the old tales off like they were so much fantasy, and Tristram -- no, the world -- has paid dearly for my arrogance.
* In ''Franchise/TheElderScrolls'' series' primary CreationMyth, this is the case for Auri-El, the [[OurElvesAreDifferent Aldmeri]] [[NobleBirdOfPrey eagle]] version of Akatosh, the [[DragonsAreDivine draconic]] God of Time and [[TopGod chief deity]] of the Aedric pantheon. In his only known moment of weakness, he agreed to help [[TheMaker Lorkhan]] create Mundus (the mortal plane) in exchange for the privilege of being its king. However, Auri-El was disgusted with what they had created and insisted that everything was permanently spoiled, and all they would be able to do would be to teach the elves to suffer with dignity. He went to war with and vanquished Lorkhan, then [[AscendToAHigherPlaneOfExistence ascended to heaven]] in full observance of his followers so that they might learn the steps needed to escape the mortal plane.
* With you playing as EvilGenius, in, well, ''VideoGame/EvilGenius'', you get to inflict one of these on one of the [[HeroAntagonist Super Agents of the Forces of Justice]] in order to be permanently rid of him -- specifically, A.N.V.I.L.'s ArrogantKungFuGuy Jet Chan. [[spoiler:He's gone so long without losing a fight that it's gone to his head, something which his old master will tell you when you interrogate him. You can then set up a one-on-one match between Jet and one of your own martial artists while also drugging his sushi prior to said match; when he loses he will be so ashamed he will retreat into the mountains and meditate upon his loss, never to bother you and your secret island base again.]]
* In ''VideoGame/FinalFantasyVII'', Cloud feels regret over several failures. His [[spoiler: failure to become a SOLDIER, the death of Zack who died trying to protect him, and blaming himself for not being strong enough to protect his childhood friend, Tifa, when she falls into a ravine and slips into a coma (also didn't help that Tifa's father blamed Cloud for Tifa's injury)]] leads to Cloud suffering from psychological disorders like TraumaInducedAmnesia and SplitPersonality. He also regrets failing to prevent [[ILetGwenStacyDie the death]] of [[spoiler: Aeris]], which motivates Cloud to take down Sephiroth.
** In the prequel ''VideoGame/CrisisCore'', Zack's failure in capturing Genesis and preventing the [[spoiler:death of Angeal]] also fall into this category.
* In ''VideoGame/FinalFantasyXIV'', the Crystal Braves is this for Alphinaud; [[spoiler:Alphinaud had intended for the Crystal Braves to be the saviors of Eorzea, but his hubris caused him to miss the smaller details and not realize the Monetarists for Ul'dah had gotten their hands on them via funding. This allowed the scheming Teledji Adeledji to seemingly assassinate Ul'dah's Sultana Nanamo Ul Namo and frame the Scions of the Seventh Dawn for it.]]
* The events of the original God of War trilogy, his DealWithTheDevil with Ares and the deaths of his wife and daughter by his hands are these for an OlderAndWiser Kratos in ''VideoGame/GodOfWarPS4''.
* In ''VideoGame/TheHalloweenHack'', [[spoiler: Dr. Andonuts]] blames himself for [[spoiler: the deaths of his wife and the Chosen Four]].
* ''Franchise/{{Halo}}'':
** In the [[AllThereInTheManual backstory]] for ''VideoGame/HaloReach'': both Carter and Kat consider the same event, the death of their squadmate Thom, to be Their Greatest Failure. Kat planned the operation he was killed on, while Carter blames his "inadequate team preparation." However, to quote their commanding officer:
---> "''Eventually I hope to be able to get it through their thick [[SuperSoldier Spartan]] skulls that Thom is dead because he chose to pursue a group of enemy combatants ON HIS OWN rather than wait for backup''."
*** For the record, [[HeroicSacrifice they're all wrong]].
** The backstory, particularly ''Literature/TheForerunnerSaga'', shows that the Didact seems to consider his ''life'' to be this trope. Particularly his hand in nearly wiping out humanity over a misunderstanding, losing every one of his children in the effort, being defeated by the Builders in his efforts to prevent and safeguard against the inevitable return of the Flood, and [[spoiler:getting marooned in Flood-infected territory by the Master Builder without completing the potentially galaxy-saving mission he was sent on by his wife, where he ends up transforming into a genocidal madman, forcing his own wife to seal him away]]. To top it off, [[spoiler:even the sane copy of himself imprinted upon Bornstellar gets forced to commit galactic genocide in order to defeat the Flood, via the same drastic methods the original Didact fought against in his aforementioned failure with the Builders, killing his wife in the process]]. This guy just couldn't catch a break (except for that thousand-year coma he was forced to go into after the again-aforementioned struggle against the Builders [[spoiler:and the 100,000+ year exile his wife put him into]]).
* Ethan Mars from ''VideoGame/HeavyRain'' believes that his son Jason's death was his fault, and seems to suffer some degree of PTSD as a result.
* ''VideoGame/InazumaEleven'': Goenji Shuuya (Axel Blaze) blames himself for [[IllGirl his sister's serious accident]] a year before the game's event because playing a national soccer tournament [[spoiler: against Teikoku lures bad guys into harming his family and]] put his sister into a coma, but is snapped out of a Wangst state by TheHero's {{Hot Blooded}}ness. Then he is determined to win a Football Frontier tournament for his sister.
* If we allow ''VideoGame/JoJosBizarreAdventureAllStarBattle'' a bit of canonicity, specifically its post-fight comments, [[spoiler:Fugo never forgave himself for not getting on the boat with the rest of Buccellati's group]].
* ''Franchise/KingdomHearts'' has Riku. He is so ashamed of allowing his heart to be consumed by darkness that he spends an entire game avoiding Sora and reluctant to return home [[spoiler:even after Xehanort's shadow is removed and his form returned]]. Then, in a journey through dreams, he notes that the results of his failure (namely, having his body stolen by Ansem) just keeps coming back to haunt him.
--> '''Riku:''' I gave in to the darkness once. And ever since, it's haunted me in some form or another. The Heartless of the man who stole my body, a puppet replica of the shadows within my heart, and now I'm facing myself.
* ''VideoGame/LightningReturnsFinalFantasyXIII'': Snow and Noel feel this way regarding [[spoiler: their inability to prevent Serah's death]].
* In ''VideoGame/MetroidOtherM'', Samus's falling out with Adam is implied to be a result of her greatest failure. The incident in question turns out to be [[spoiler:trying to get Adam to change his mind about leaving his brother Ian on a ship that is about to explode, making an already hard decision even harder]].
* In the ''[[VideoGame/SamAndMaxFreelancePolice Sam & Max]]'' game ''[[VideoGame/SamAndMaxTheDevilsPlayhouse The City that Dares Not Sleep]]'', [[spoiler: Sam's greatest failure is not being able to rescue Max from "The Final Imperative;" Max was KilledOffForReal, and most of the game's ending scene follows Sam's guilt and grief over Max's death. He seems to get over it by ''VideoGame/PokerNight2'' and doesn't mind that the Max with him now is from an AlternateUniverse, where Sam is the one who died]].
* In ''VideoGame/MetalGearSolid4GunsOfThePatriots'' [[spoiler: Big Boss]] views the killing of his mentor and friend who taught him everything he ever knew as a soldier and then going on to fight for causes that she never would have believed in as his greatest failure. He goes so far as to claim after that point he was already dead emotionally. At the end of Metal Gear Solid 4 as he stands above her grave, [[spoiler: Big Boss]] proclaims to his son that if their roles had been reversed, he probably wouldn't have made the same mistakes and that he still has a chance to do things better than he ever had.
* In ''VideoGame/{{Okami}}'', when [[spoiler: Waka tried to save the Celestials using the Ark Of Yamato]], he didn't realise that [[spoiler:Yami]] was on board, leading to the [[spoiler: Celestials]] getting slaughtered. It also led to a horde of demons being [[spoiler:unleashed in Nippon]].
* In ''VideoGame/{{Persona 3}} FES'', one of the things The Answer deals with is [[RobotGirl Aigis's]] Greatest Failure. That is, [[spoiler: her inability to prevent the Protagonist's death despite her promise to protect him]].
* General Azimuth in ''VideoGame/RatchetAndClankFutureACrackInTime''. A plot point in ''VideoGame/RatchetAndClankFutureToolsOfDestruction'' was that BigBad Tachyon took over because he had access to Lombax technology. ''Azimuth'' was the one who granted him access, as he believed Tachyon would help improve them to better the galaxy. The result was that the Lombax people had to take refuge in an alternate dimension, with Azimuth being left behind as punishment. To this end, Azimuth hoped to use The Great Clock to SetRightWhatOnceWentWrong... no matter what the cost.
-->'''Ratchet:''' Why aren't you with the other Lombaxes?
-->'''Azimuth:''' ''Because I failed them!'' I... I failed them...
* According to the [[http://www.seriouszone.com/ssgold/festory.php original backstory]], ''VideoGame/SeriousSam'' was the captain of the starship that drew Mental's attention to humanity and he threw himself headlong, even suicidally, into the fighting to try and atone.
* In ''VideoGame/SpiritsOfAnglerwoodForest'', [[spoiler: Ezra]] feels extremely guilty for cursing his family since he feels it robbed him and Phoebe of a normal life. So guilty, in fact, that he [[spoiler: goes deep into the woods alone to put a stop to it]]. [[FromBadToWorse It doesn't work]].
* Asbel of ''VideoGame/TalesOfGraces'' considers his biggest failure to be his inability to protect his friends during the Prologue sequence, which leads to [[spoiler: Sophie's HeroicSacrifice (though she gets better in a few years)]]. This kickstarts the basis for his entire [[DeclarationOfProtection character arc]].
* In ''VideoGame/TalesOfSymphonia'', Lloyd and Genis are most troubled by the mutation and death of their friend Marble after Lloyd had been caught sneaking into the ranch to visit her with Genis, which also led to an attack on Iselia. It's made worse when her granddaughter Chocolat refuses to be rescued after learning this.
** Sheena is also burdened by her failure to make a pact with Volt, even though she was unable to understand what he was saying and (unbeknownst to her at the time), he no longer wanted to make a pact.
** Kratos has at least ''two'' of these, both spoilery: [[spoiler:his inability to prevent Mithos from falling into despair after Martel's death, and being forced to kill his wife after she was turned into a monster. No wonder he's a DeathSeeker]].
** Regal considers [[spoiler: Alicia's death]] to be this, to the point he [[HonorBeforeReason refuses to remove his handcuffs because they are a symbol of his crime]].
* In ''VideoGame/TalesOfTheAbyss'', Jade's backstory includes having accidentally killed his teacher with experimental magic as a child. He's mostly gotten past it now, but it drove him to extreme lengths trying to make a ReplacementGoldfish for about ten years until Peony knocked some sense into him.
** The magic he developed in this time -- [[spoiler: fomicry, used for making clones called "replicas"]] -- is what kicks off the whole plot, [[spoiler: allows the main character, a replica, to exist]], and forms the basis for the [[BigBad Big Bad's]] plan. In a way, ''Tales Of The Abyss'' overall is Jade Curtiss' greatest failure. He is very aware of this.
--->'''Jade''': I wish I could go back in time and [[spoiler: kill myself as a newborn]].
* In ''VideoGame/TearsToTiara2'' Enneads and Monomachus, first leaders of LaResistance and then of Hispania and Hamil's advisers have the same two events. First, [[ILetGwenStacyDie they had failed to protect Hamil's father and their old commander Hasdrubal]]. Second, they had both failed to see through Hamil's ObfuscatingStupidity to help him as he does his best to lessen the burden of the people of Hispania under the oppression of TheEmpire and only thought of rebellion, going as far as planning to use Hamil as a puppet.
* ''VideoGame/WorldInConflict'': For Colonel Sawyer, it was the use of the tactical nuclear warhead during the battle of Cascade Falls. Later, he throws caution to the winds and pushes his forces into high-casualty head-on assaults to ensure using another one never becomes necessary.
--> Sawyer: I won't let this become another failure, like Cascade Falls.
--> Webb: But... we didn't fail at Cascade Falls, sir.
--> Sawyer: When I have to sacrifice a company of my men and drop a nuke on my own country, I'LL CALL IT A GOD-DAMNED FAILURE!
* Real-life example with Blizzard concerning their on-going development of ''VideoGame/WorldOfWarcraft'' where they flat-out stated during a Blizzcon interview that their biggest regret for the franchise was not creating Azjol-Nerub into a world zone during the ''Wrath of the Lich King'' era.
** Grom Hellscream came to view his decision to seal the pact between the orcs and demons as this, even choosing to hide his involvement from Thrall.
** Thrall sees making Garrosh Hellscream the Horde Warchief as one of his greatest failures, because he felt he had to look after Grom's son and it killed his best friend and many others, including causing one of his friends to hate him and go OmnicidalManiac. It kind of WAS Thrall's greatest failure...
* [[TheHero Rean Schwarzer]] in ''VideoGame/TheLegendOfHeroesTrailsOfColdSteel II'' believes that his greatest failure was him not bringing back Crow to Thors school as Crow dies in Rean's arms at the end of the main storyline of ''Cold Steel II''. And in ''Cold Steel III'', [[spoiler:letting Millium die right in front of his eyes is another moment of failure for him.]]
* In ''VideoGame/MegaMan11'' it's revealed that Dr. Light feels this way about Dr. Wily. Though their friendship was already strained by that point, the straw that broke the camel's back was Light speaking out against Wily's Double Gear System and convincing the department to choose his research into robots with independent thought instead. This finally broke their friendship once and for all and also managed to be Wily's StartOfDarkness, which Light still regrets to this day:
--> '''Dr. Light:''' Wily never forgave me. And his views have grown ever more extreme since then... How ironic. That my efforts to quench Wily's hotheadedness before it led him astray... only ended up fueling the fire. If only I'd shown him there was a way to work together... instead of just telling him that he was wrong, maybe we'd still be friends.
* ''VideoGame/RedDeadRedemption2'': [[spoiler:Accidentally beating the sick-and-dying family man Thomas Downes to death over a debt is this for Arthur, for different reasons depending on his honor; at high honor, it's for finally making him realize just how often (and how badly) he's ruined innocent lives, with the Downes family just being the biggest and most obvious. At low honor, it's because it's how Arthur [[YourDaysAreNumbered contracts tuberculosis]], signing his death warrant. Made clearest by the following sidequests revolving around the Downeses, as well as the speech (both honor variants) he gives [[LoanShark Leopold Strauss]] upon kicking him out of camp after finishing the Debtor missions.]]
* In ''VideoGame/FateGrandOrder'': [[spoiler: Avicebron]] feels immense shame and guilt for his actions in [[spoiler: [[LightNovel/FateApocrypha the Greater Grail War]]]] - specifically [[spoiler: [[TreacheryIsASpecialKindOfEvil betraying his master]] [[WouldHurtAChild Roche]], and [[PoweredByAForsakenChild using him as a core for his Golem, Adam]]]] - to the point where he considers it the worst thing he's ever done, and badly wants to [[TheAtoner atone]]. Unusually for this trope [[spoiler: Avicebron]] only hazily remembers the actual crime, since he's a Servant, and Servants aren't supposed to retain memories between Grail Wars, but the fact he remembers it ''at all'' just emphasizes how bad it actually was: his crime was so severe, it permanently damaged his Saint Graph and followed him into the Throne Of Heroes - his crime was actually horrible enough to ''mar his very legend as a hero''. [[spoiler: He finds some degree of redemption by making a HeroicSacrifice: turning ''himself'' into Adam's core, and handing control over to the player so they can save the world with it]].
[[/folder]]

[[folder:Visual Novels]]
* Many of the prized possessions in ''VisualNovel/FleuretBlanc'' are, in fact, reminders of these. You usually only discover this after winning them and reading either the item description or Squeaker's commentary.
** Le Neuvieme's grimoire is a reminder of [[spoiler:how he disappointed his family by straying from the family profession, and the obligations he still holds]].
** Amara's metronome is a reminder of a time she failed to uphold her ideal of perfection and damaged the metronome during fencing practice.
** Junior's stuffed animal is a reminder of a childhood embarrassment in which she discovered that for all her technical prowess and determination, there are some skills she is not capable of.
* Ed from ''VisualNovel/{{Policenauts}}'' can't use a gun anymore because of [[spoiler: shooting Marc's father in front of Marc, who was revealed to be Ridley, Tony's brother. However, he does use a gun when he [[BigDamnHeroes saves Jonathan from being shot by Gates]]]].
* ''VisualNovel/{{Grisaia No Kajitsu}}'': Amane and Sachi are living with this kind of regret:
** Amane: [[spoiler: When her entire class got stranded in a ravine after an accident, things went to hell, the situation escalated until the survivors resorted to eating their dead classmates, something Amane and her best friend Kazuki not participated in; in fact, Amane didn't even now they were doing that. When she and Kazuki try to escape, the crazed survivors try to chase them down and Amane is forced to leave Kazuki behind. She feels personally responsible for Kazuki's death, living the rest of her life believing she does not deserve happiness.]]
** Sachi: [[spoiler: After her previously caring parents grow distant to her, being buried by work, Sachi doubles her effort both in school and home the earn their attention, but with little success. An entire year of neglect later on her 10th birthday, her parents seemingly come around suddenly, which angers Sachi and she runs away. Just when her parents find her at the local playground, they are run over by a truck right in front of Sachi's eyes. She convinces that it was her fault, for not being reasonable, and toughing out the neglect, this belief leads to severe mental issues for her.]]
* ''VisualNovel/MonsterProm'': In a secret route, [[OurVampiresAreDifferent Liam]] reveals that he has two: [[spoiler: getting [[TheNthDoctor the second Hope]] killed, which led to his fractured relationship with the Coven, and choosing [[Series/BuffyTheVampireSlayer Angelus]] as his villain name]].
[[/folder]]

[[folder:Webcomics]]
* A villainous example in ''Webcomic/DanAndMabsFurryAdventures'': Dark Pegasus made a plan to take over the kingdom of H-Ann, a country renowned for its stable defenses and the protection of their citizens. However, he ''rushed'' his plans, and when it all backfired on him, he started making less and less stable ones. At the point of the comic, he's returned from the dead multiple times (and it's implied that he CameBackWrong), and his family are more than a bit concerned about how lopsided those plans have become.
* ''Webcomic/ElGoonishShive'':
** Grace cowered as Damien went on a killing spree breaking her and her brothers out of the lab that created them. Grace later finds out that she was created to fight Damien, and her guilt over failing to act the first time overcomes her pacifistic tendencies and drives her [[UnstoppableRage berserk]] when Damien threatens to kill Nanase and Ellen. Despite saving her friends' lives and freeing her brothers by defeating Damien, she feels even ''more'' guilty for losing control and then failing to keep him from committing suicide. This hat trick of perceived failure leads her to swear off using her shapeshifting powers until her sister and grandfather convince her to stop blaming herself.
** Mr. Raven holds himself responsible for Tedd's mother having divorced his father and not having any further contact with her son. It's not entirely clear what happened, but from his reactions, it seems that Raven's zeal for fighting evil went a bit too far and pushed Mrs. Verres down a self-destructive path.
* ''Webcomic/{{Homestuck}}'':
** Even after [[ArcNumber 413]] years, WV still won't let himself forget that he failed to prevent [[spoiler:Jack from murdering his army]].
** Equius still regrets failing to protect [[spoiler:Nepeta. When he and Nepeta find themselves fused to other characters as sprites, he apologizes to her, admitting that his refusal to do anything against Gamzee due to the blood cast was the wrong idea]].
** Kanaya regrets her failure to protect [[spoiler:the Matriorb]].
* ''Webcomic/MagicalTwelfthGraders'': Namgung blames himself for Gyeowul's death, and wishes more than anything that he can fix it--but the wish that the pin grants can't be used to revive the dead. [[spoiler:He can, however, use it to turn back time, but he can't turn it back to before the moment where she died. He's still tried a dozen times]].
* ''Webcomic/TheOrderOfTheStick'':
** Vaarsuvius is a highly intelligent elven wizard with a large ego. This sets them up for a fall on two occasions:
*** Their ego takes a severe beating when they're unable to defeat a highly spell-resistant death knight, fail to prevent the hobgoblins from overrunning the breach at Azure City and winning the battle (including having fleeing allied soldiers ''beg'' V to help them and one of them cursing the elf's "useless goddamn magic" with her dying breath after V is unable to help them due to having run out of spells), and then spends months trying to overcome the effects of an anti-scrying abjuration without luck, in a situation when the fate of the world practically hinges on the elf's success. The long-term consequences for Vaarsuvius remain yet to be revealed, but in the short term, they certainly include {{Past Experience Nightmare}}s, every symptom in the book for Post Traumatic Stress Disorder, and easy temptation to a FaceHeelTurn when their self-perceived lack of ability puts their family in danger. Based on [[http://www.giantitp.com/comics/oots0715.html this strip]], it looks like V isn't going to live down that FaceHeelTurn, either.
*** After that is the realization that the Familicide spell V used during said FaceHeelTurn [[spoiler: wound up being responsible for the death of a staggering number of innocent people]].
** Elan gets a bit of this when the half-orc Therkla is killed trying to protect him. She's poisoned, and Elan lacked the Bard spell that would have cured her. It affects Elan enough that when he reunites with Haley, he reveals that he took "Neutralize Poison" at his next level up.
* ''WebComic/StandStillStaySilent'': When he was thirteen, Lalli's MathematiciansAnswer in a scout report caused a group of soldiers from his military base to venture into a dangerous area and four people to be killed. The number was considered low in regards to the attack's violence. His older cousin reprimanded him quite harshly about it, and during the scolding implied that a single mistake from their grandmother was the reason they had left their old home to live on that military base five years before that event. In the present day, it causes Lalli to prefer fixing a mistake in finding a path while half-asleep to leaving it hanging and forcing the rest of the crew to backtrack. When he couldn't find a safe path to a new campsite, he put himself into a PowerStrainBlackout to create one via clearing a tunnel full of [[PlagueZombie troll]] pods.
* In ''Webcomic/WeakHero'', Alex holds himself responsible for Ben's arm injury, as not only was Ben protecting him, but it was Alex getting involved with the wrong crowd that led to them both being at the construction site in the first place. Even though Ben constantly tells him not to blame himself, Alex can't help but do so.
[[/folder]]

[[folder:Web Original]]
* ''{{WebVideo/Gameboys}}'' - Cairo, when he ran away in fear when he was outed to his family. His father got sick of COVID-19 while looking for him, and eventually passes away. His older brother London is upset with him over this. The two siblings get better, though.
* In ''Literature/GreekNinja'', Sasha fails to save her sensei during the invasion of Ariadnio.
* Agent Carolina from Machinima/RedVsBlue is this in SO many spades over her previous [[CompetitionFreak overly-competitive]] nature to please her disconnected father so long ago, where she had a great many opportunities to drive off her self-destructive path of proving herself to Project Freelancer, with the Project itself destroying the other Freelancers' lives over time during its ruinous slog of development of its AI Fragments during the years of its activity. she definitely feels multiple ripples of this '''BIG time''' after many of her former comrades died, earning the eternal vengeance of an [[PlayingWithFire inferno-obsessed]] [[PyroManiac pyromaniac]] and seemingly forgets a time she accidentally killed a '''very''' dear friend of a Simulation Trooper, thus having him vengefully haunt her later on in the future and giving her a VERY '''[[WaxMuseumMorgue horrific]]''' view of what happened to the other surviving agents leftover from the disbanded Project Freelancer. She especially gives [[spoiler: a past version of herself a '''very scathing''' "talk" involving her aforementioned self-destructive victory-obsessed-self, essentially [[IHatePastMe hating on her past-self a very great deal.]] ]]
* ''Literature/WhateleyUniverse'': Captain Patriot of SPECTRUM once talked a young mutant into surrendering to the MCO: the kid promptly disappeared and was never seen again, and the MCO still steadfastly denies he even existed. He will go rogue before he lets the MCO get their hands on Stacey and makes sure they know it.
* ''WebAnimation/{{RWBY}}'': Jaune Arc is hit hard with that. He blames his own weakness and inability to stop [[StarCrossedLovers Pyrrha]] from fight Cinder as the reason why his partner and best friend dies. Not be able to recognize that Pyrrha was actually in love for him made that worse to Jaune. It takes until Volume 6 to Jaune forgives himself, but he still misses her and mourns her absence. Part of his current armor and weapons are made to honor Pyrrha's memory.
[[/folder]]


[[folder:Western Animation]]
* ''WesternAnimation/DuckTales2017'':
** Della Duck and the ''Spear of Selene'' was this to Scrooge. He had a made a special surprise for his niece Della to celebrate the birth of her children; a rocket known as the ''Spear of Selene''. No one knew about it because Scrooge told no one about this secret little project he had in the works. Unfortunately, Della had this knack for digging into things she's not supposed to be digging into, and to make matter worse, the rocket wasn't even properly tested. Della hijacked the rocket and took it for a ride in orbit, one which seemingly proved to be her last. Scrooge tried to guide Della through the cosmic storm, only for lightning to hit the ''Spear of Selene'', causing the rocket to lose contact with Scrooge and [[spoiler: ironically force Della to crash on the moon]]. Scrooge was willing to go as far as to bankrupt himself, trying to find her somewhere lost in outer space only for the same event to likely befall his crew. The search for Della wound up costing him millions, if not ''billions'', of dollars and because it was proving fruitless, he was ultimately forced to cancel the search for Della by his staff. Until the events of ''Woo-oo!'', Scrooge had more or less become a shut-in and had never spoken to his family after what happened to Della.
* Lao Shi, Jake's grandfather and trainer in ''WesternAnimation/AmericanDragonJakeLong'', became much more focused and wise when he nearly got killed by [[BigBad the Dark Dragon]].
* ''WesternAnimation/AvatarTheLastAirbender'':
** Aang's loss to Azula in the second season finale, resulting in not only the loss of the entire Earth Kingdom but Aang's death as well. Cue Aang stealing Zuko's "I must restore my honor" speech when he gets better. He expresses a similar regret over running away, feeling that he's responsible for the escalation of the war and the destruction of the Air Nomads.
** Aang's predecessor, Avatar Roku, had several opportunities to stop his best friend Fire Lord Sozin from starting the hundred-year war in the first place. Sozin expresses to Roku that maybe he should TakeOverTheWorld to share the "greatness" of the Fire nation? Roku, without even, you know, ''explaining'' to Sozin just ''why'' this would be a terrible idea, just blows him off and says forget it. Sozin sets up colonies in the Earth Kingdom? Roku fights him off but doesn't kill him, incarcerate him, warn the Earth Kingdom and the Water Tribes of his leanings, or anything beyond telling Sozin "never try this again or else". Is there any surprise at Sozin's dick move in [[spoiler:letting him die from the poisonous gases of that volcanic eruption so he can be out of the way and Sozin can start his invasion]]? Naturally, [[spoiler:in Roku's afterlife and the twilight of Sozin's life]], both regret what happened.
** A side-story, shown as motion comics, gives Avatars Kyoshi and Kuruk one of these. Kyoshi formed the [[SecretPolice Dai Li]], which went on to assist an EvilChancellor from turning Ba Sing Se into a totalitarian city-state that carried after [[MagnificentBastard Azula]] conquered it. Kuruk wasn't a good Avatar, spending most of his time [[CompensatingForSomething impressing people with his bending prowess]]. But when he found a wife and started shaping up, [[EldritchAbomination Koh the Face-Stealer]] snatched her, possibly to punish him.
** For Uncle Iroh, it's his failed siege of Ba Sing Se during his time as a Fire Nation general. It's hinted many times that the failure isn't because of the military disgrace, but because he ''lost his son'' in the battle.
** For the first two seasons, Zuko believes his greatest failure was talking out of turn and showing weakness to his father. After he makes a HeelFaceTurn, it shifts to his betrayal of his uncle.
* Azmuth from ''Franchise/Ben10'' has two past actions that turned him into TheAtoner he is today:
** The first was when he created [[CoolSword Ascalon]], a powerful sword that could tap into the fundamental forces of the universe itself. When news of this sword broke out, an Incursean warrior stole it with hopes of using it to end the CivilWar happening on his world. Unfortunately, Ascalon was too powerful, and the warrior destroyed the world he had been trying to protect (and as another consequence, [[ArsonMurderAndJaywalking Azmuth's girlfriend left him]]).
** The second was when he unintentionally created [[AxCrazy Malware]], an incomplete and corrupted Galvanic Mechamorph that was created when Azmuth turned off the Helix (the device that created the Galvanic Mechamorphs) while it was still working on Malware. While Azmuth did try to heal him, Malware's corrupt code turned him against his creator and made vengeance against Azmuth his defining purpose.
* Number 5 of ''WesternAnimation/CodenameKidsNextDoor'' blames herself for some NoodleIncident where the Delightful Children made Number 1 bald and sees an opportunity to save a random girl from the Delightful Children as MyGreatestSecondChance.
* On ''WesternAnimation/DangerRangers'', Rusty Ringtail is this for Burble. He's a child skater who doesn't follow safety rules and Burble failed to stop his antics before.
* In the ''WesternAnimation/MightyMax'' cartoon, Norman considers his father's death at the hands of Spike to be his greatest failure. As he says, if he had been just a little faster retrieving his father's axe, "he'd still be alive today."
* Princess Celestia from ''WesternAnimation/MyLittlePonyFriendshipIsMagic'' seems to feel this way about being forced to imprison her own little sister, Luna, in the moon when Luna became [[MadGod Nightmare Moon]]. Luna, after being redeemed, seems to feel this about becoming Nightmare Moon in the first place. At one point of "Luna Eclipsed", she's seen looking forlornly at the statue of her evil self and has become TheAtoner. [[spoiler:"Do Princesses Dream of Magic Sheep" reveals that she created a nightmare-making entity to forever plague her dreams of the things she did as Nightmare Moon. Unfortunately, her guilt ended up making the entity grow strong enough to infiltrate the dreams of other ponies (i.e. ''all'' of Ponyville), with its intentions to escape into the waking realm and turn it into a dark reality. With the help of the Mane Six, Luna was finally able to let go of her guilt, enabling her to rest in peace, literally]].
** Celestia's also has Sunset Shimmer's eventual fall from grace...despite being a PhysicalGoddess, Celestia is as fallible as anyone.
* ''WesternAnimation/OKKOLetsBeHeroes'': "Let's Take a Moment" finally reveals the whole story behind the [[NoodleIncident "sandwich incident"]] that happened between Mr. Gar and K.O.'s mom Carol: [[spoiler: Back when they were El Bow and Silver Spark, working for P.O.I.N.T., Gar had a crush on Carol, who unfortunately for him was dating fellow hero Laserblast at the time. While on a stake-out, Gar tried to confess his feelings using a sandwich as a metaphor, which distracted Carol from going to back-up Laserblast, leading to a disastrous explosion that led to his mysterious disappearance. Not only did Carol blame Gar in the heat of the moment for distracting her, but Gar [[ItsAllMyFault blamed himself]] and resigned from P.O.I.N.T. He has been haunted by that event ever since, especially since he never got over his crush on Carol. After the events of "Let's Take a Moment", however, Mr. Gar finally seems to be moving past it.]]
* ''WesternAnimation/SheRaAndThePrincessesOfPower'':
** Angella deeply regrets ordering the battle in which her husband died [[spoiler:or, rather, was captured and sent to Beast Island]]. It causes her to be somewhat overprotective to her daughter, Glimmer, although they eventually work their way past it.
** Adora has a tendency to [[ItsAllMyFault blame herself for everything that goes wrong]], no matter how tenuous the logical connection, but [[spoiler:Angella's HeroicSacrifice]] clearly weighs heavily on her for the fourth season. [[spoiler:When Glimmer blames her for Angella's death during an argument, Adora's eyes fill with tears, and Glimmer definitely realises that she's crossed a line.]]
** [[spoiler:When Scorpia gets the chance to process the portal incident, she comes to view failing to act when Catra betrayed Entrapta as her worst action. It prompts her to pull a HeelFaceTurn, quit the Horde and defect to the Princess Alliance in the hope of getting them to rescue her best friend.]]
** [[spoiler:It looks like this is going to be how Glimmer views trying to tap the Heart of Etheria, and thereby nearly destroying the world, in the wake of the fourth season finale. Even while it's going on, she claws herself to her feet in a frantic attempt to fix it.]]
* In ''WesternAnimation/StevenUniverse'' Steven considers his inability to talk down [[spoiler: Jasper, Bismuth, and Eyeball]] and their subsequent fates to be his biggest failure, which he finally confronts his feelings towards in "Mindful Education".
* In ''WesternAnimation/TeenTitans'', Robin considers Red X to be this, not only because the plan didn't work, but because it caused him to lose the trust of the rest of the team, and he was lucky he got it back. This is made only worse when someone steals the equipment and becomes the villain again. Nothing can convince him that it isn't anyone's fault but his own (and he has a point).
* ''Franchise/{{Transformers}}'':
** ''WesternAnimation/TransformersAnimated'':
*** Optimus's greatest regret is [[spoiler:the incident on Archa Seven that he thought cost Elita-1 her life. It only worsened when he found out what ''really'' happened to Elita]].
*** Ratchet has two regrets from the Great War. He regrets erasing Arcee's memory, at her request, to prevent her intel from falling into Decepticon hands, especially since she became completely amnestic as a result. Second, he feels that he failed as a mentor to Omega Supreme.
*** Prowl blames himself for not being present when his master and dojo were destroyed by Decepticons during the war. This was made worse because he tried to use a protoform to revive his master who came back to life and immediately rebuffed him for using a new life to revive an old one before relinquishing his spark. This resulted in Prowl becoming even more of a loner and failing to fully grasp his master's teachings until years later when he met Optimus's crew and came to Earth.
** ''WesternAnimation/TransformersPrime'':
*** Arcee takes the deaths of her partners Tailgate and Cliffjumper very personally. Whenever either of them comes up in conversation, her normally assertive confident personality slips into [[BerserkButton rage]], and the possibility of it happening ''again'' turns her into a nervous self-doubting train wreck of a person.
*** Ratchet greatly regrets not being able to save Bumblebee's voicebox even though he saved his life during the Great War. [[spoiler:His guilt was finally put to rest when Bumblebee regained his voice after falling into the Decepticons' cybermatter during the FinalBattle. What made it better was that it was Rachet's synthetic energon formula that helped create the cybermatter]].
---->'''Optimus Prime''': It would seem the old field medic made good after all.
** In the third season of ''WesternAnimation/TheTransformers'', Optimus Prime's successor, Rodimus Prime (formerly Hot Rod) doubted his abilities to fill Optimus's shoes, in part because during Optimus's last stand, Hot Rod tried to join the battle and help, only to wind up being used as a hostage/shield by enemy leader Megatron--had Hot Rod not stepped in, Prime may have survived. Visiting Prime on his deathbed, Rodimus asked for forgiveness... But Prime slipped away before he could forgive Rodimus.[[note]]Although he did [[spoiler: promote Rodimus to Prime through the Matrix, so that probably implies forgiveness]].[[/note]]
** ''WesternAnimation/TransformersCyberverse'' gives Optimus Prime two. He feels that he didn't do enough to stop Megatron before he was too far gone. He also regrets his decision to send the Allspark away from Cybertron to keep it out of Decepticon hands. The plan works, but he did not realize that the relic's absence would cause the planet to sicken and die.
* For Splinter in ''[[WesternAnimation/TeenageMutantNinjaTurtles2012 Teenage Mutant Ninja Turtles (2012)]]'', it was the act of allowing [[spoiler: his temper to get the better of him when Oroku Saki insulted him in front of Tang Shen. The resulting attack intensified the rivalry between Oroku Saki and Hamato Yoshi (as Splinter was previously known as), eventually leading to Tang Shen's death, and Yoshi/Splinter's daughter being kidnapped]]. This is why when it comes to [[HairTriggerTemper Raphael's]] temper, Splinter treats it as SeriousBusiness.
* Subverted in, of all places, ''WesternAnimation/{{Ultimate Spider-Man}}''. A new villain Nightmare uses his powers to transport the team into dream worlds where he makes them confront their greatest fears. Spider-Man is forced to come face-to-face with his murdered Uncle Ben... and strikes up a pleasant conversation with him. Nightmare is shocked that Peter isn't grieving and Peter tells him why it's not working. Yes, Peter regrets what happened to Uncle Ben, but he turned that tragedy into something good by becoming Spider-Man, a hero. So if he expects a guilt trip to keep him from kicking his butt, he's got the wrong person.
[[/folder]]

[[folder:Web Videos]]
* ''{{WebVideos/Gameboys}}'' - Cairo, when he ran away in fear when he was outed to his family. His father got sick of COVID-19 while looking for him, and eventually passes away. His older brother London is upset with him over this. The two siblings get better, though.

[[/folder]]

* In ''WesternAnimation/MyLittlePonyEquestriaGirlsRainbowRocks'', former BigBad Sunset Shimmer feels this way about her previous actions in [[WesternAnimation/MyLittlePonyEquestriaGirls1 the first movie]]. As an AlphaBitch who ran the school with an iron fist, Sunset's HeelFaceTurn has been met with [[ReformedButRejected rejection by the students of Canterlot High School]]. Even as Sunset tries to improve, her low self-esteem gets [[FlawExploitation exploited to keep her quiet]] after Sunset finds out about the plans of [[EnthrallingSiren the Dazzlings]].

* Mr. Incredible in ''WesternAnimation/TheIncredibles'' blames himself for spurning Buddy (later known as Syndrome), his biggest fan. Later, Buddy turns to evil. Subverted as Buddy points out that Mr. Incredible hadn't given him a single thought until he became Syndrome.

* ''ComicBook/SpiderMan'' didn't stop the burglar that would shoot his Uncle Ben (in various tellings, because of spite, laziness, or arrogance); later, he was [[ILetGwenStacyDie unable to prevent his girlfriend Gwen Stacy from being killed]] by the [[ComicBook/NormanOsborn Green Goblin]]. The latter is not helped by how his using his webbing in an attempt to save her caused her neck to snap from the recoil, a fact Marvel initially attempted to gloss over but has recently admitted (through, among others, ''What If?'' - where he saves her by diving in after her instead - and ''ComicBook/SpiderGirl''). It's made pretty clear that he at the very least thinks this is what happened, as he makes it a point to use multiple weblines when saving people, and Iron Man recalls Peter telling him of the incident.

* In the ''Franchise/BackToTheFuture'' fanfic ''FanFic/BackToTheFuturePrequel'', Doc still regrets the day [[spoiler: one of his inventions malfunctioned and crippled Holly Webb]].

* Integrity's death is this for [[Characters/UndertaleSans Sans]] in ''Fanfic/NotAsSimpleAsAHappyEnding''.

* In ''Franchise/TheElderScrolls'' series' primary CreationMyth, this is the case for Auri-El, the [[OurElvesAreBetter Aldmeri]] [[NobleBirdOfPrey eagle]] version of Akatosh, the [[DragonsAreDivine draconic]] God of Time and [[TopGod chief deity]] of the Aedric pantheon. In his only known moment of weakness, he agreed to help [[TheMaker Lorkhan]] create Mundus (the mortal plane) in exchange for the privilege of being its king. However, Auri-El was disgusted with what they had created and insisted that everything was permanently spoiled, and all they would be able to do would be to teach the elves to suffer with dignity. He went to war with and vanquished Lorkhan, then [[AscendToAHigherPlaneOfExistence ascended to heaven]] in full observance of his followers so that they might learn the steps needed to escape the mortal plane.

[[quoteright:300:[[Franchise/StarWars https://static.tvtropes.org/pmwiki/pub/images/stormtrooper_failure_2150.jpg]]]]

[[folder:Web Comics]]

* In ''Webcomic/ElGoonishShive'', Grace cowered as Damien went on a killing spree breaking her and her brothers out of the lab that created them. Grace later finds out that she was created to fight Damien, and her guilt over failing to act the first time overcomes her pacifistic tendencies and drives her [[UnstoppableRage berserk]] when Damien threatens to kill Nanase and Ellen. Despite saving her friends' lives and freeing her brothers by defeating Damien, she feels even ''more'' guilty for losing control and then failing to keep him from committing suicide. This hat trick of perceived failure leads her to swear off using her shapeshifting powers until her sister and grandfather convince her to stop blaming herself.
** Mr. Raven from the same series holds himself responsible for Tedd's mother having divorced his father and not having any further contact with her son. It's not entirely clear what happened, but from his reactions, it seems that Raven's zeal for fighting evil went a bit too far and pushed Mrs. Verres down a self-destructive path.
* ''{{Webcomic/Homestuck}}'': Even after [[ArcNumber 413]] years, WV still won't let himself forget that [[spoiler: he failed to prevent Jack from murdering his army]].
** Equius still regrets [[spoiler: failing to protect Nepeta. When he and Nepeta find themselves fused to other characters as sprites, he apologizes to her, admitting that his refusal to do anything against Gamzee due to the blood cast was the wrong idea]].
** Kanaya regrets [[spoiler: her failure to protect the Matriorb]].
* ''Webcomic/MagicalTwelfthGraders'': Namgung blames himself for Gyeowul's death, and wishes more than anything that he can fix it--but the wish that the pin grants can't be used to revive the dead. [[spoiler:He can, however, use it to turn back time, but he can't turn it back to before the moment where she died. He's still tried a dozen times]].
* Vaarsuvius from ''Webcomic/TheOrderOfTheStick'' is a highly intelligent elven wizard with a large ego. That ego takes a severe beating when the elf is unable to defeat a highly spell-resistant death knight, fails to prevent the hobgoblins from overrunning the breach at Azure City and winning the battle (including having fleeing allied soldiers ''beg'' him/her to help them and one of them cursing the elf's "useless goddamn magic" with her dying breath after V is unable to help them due to having run out of spells), and then spends months trying to overcome the effects of an anti-scrying abjuration without luck, in a situation when the fate of the world practically hinges on the elf's success. The long-term consequences for Vaarsuvius remain yet to be revealed, but in the short term, they certainly include {{Past Experience Nightmare}}s, every symptom in the book for Post Traumatic Stress Disorder, and easy temptation to a FaceHeelTurn when his/her self-perceived lack of ability puts his family in danger.
** And based on [[http://www.giantitp.com/comics/oots0715.html this strip]], it looks like V isn't going to live down that FaceHeelTurn, either.
** Supplanted now by the realization that the Familicide spell (s)he used during said FaceHeelTurn [[spoiler: wound up being responsible for the death of a staggering number of innocent people]].
** Elan gets a bit of this when the half-orc Therkla is killed trying to protect him. She's poisoned, and Elan lacked the Bard spell that would have cured her. It affects Elan enough that when he reunites with Haley, he reveals that he took "Neutralize Poison" at his next level up.
* ''WebComic/StandStillStaySilent'': When he was thirteen, Lalli's MathematiciansAnswer in a scout report caused a group of soldiers from his military base to venture into a dangerous area and four people to be killed. The number was considered low in regards to the attack's violence. His older cousin reprimanded him quite harshly about it, and during the scolding implied that a single mistake from their grandmother was the reason they had left their old home to live on that military base five years before that event. In the present day, it causes Lalli to prefer fixing a mistake in finding a path while half-asleep to leaving it hanging and forcing the rest of the crew to backtrack. When he couldn't find a safe path to a new campsite, he put himself into a PowerStrainBlackout to create one via clearing a tunnel full of [[PlagueZombie troll]] pods.

* With you playing as EvilGenius, in, well, ''VideoGame/EvilGenius'', you get to inflict one of these on one of the [[HeroAntagonist Super Agents of the Forces of Justice]] in order to be permanently rid of him -- specifically, A.N.V.I.L.'s ArrogantKungFuGuy Jet Chan. [[spoiler:He's gone so long without losing a martial arts fight that it's gone to his head, something which his old master will tell you when you capture and interrogate him. You can then set up a one-on-one match between him and one of your own martial artists while also drugging his sushi prior to said match; when he loses he will be so ashamed he will retreat into the mountains and meditate upon his loss, never to both you and your secret island base again.]]

** There's the stormtrooper in the picture at the top of the page (Those WERE the droids he was looking for). The 2017 book ''Literature/FromACertainPointOfView'' has a story about that stormtrooper.

'''Luke''': I'm sorry.

** Principal Asano turns out to have his ruthlessness rooted in a failure as well. [[spoiler:He used to be a kind-hearted and caring teacher much like Koro-sensei, but then one of his former students committed suicide in high school. He blamed himself for not preparing the boy for life properly, and his current brutal teaching techniques are the result of him trying to emphasize strength of will in his pupils, even if he has to resort to using ThePowerOfHate as a motivator.]]

** Major Armstrong, Colonel Mustang, Riza Hawkeye and several other veterans of Ishval have deep regret and seek to atone for the massacre.

** ''Anime/MobileSuitGundamSEED'': Kira Yamato has two of these. The first time being the failure of saving a shuttle full of fleeing civillians, one of them being a little girl he recently befriended. The second time was when he failed to save [[spoiler:Flay Allster, his first love]].

*** Athrun also seems to feel this way towards Shinn in the later half of ''[[Anime/MobileSuitGundamSEEDDestiny Destiny]]'' because he couldn't help him see through Durandal and Rey's manipulations.

* Tomiko from ''Manga/IsKichijojiTheOnlyPlaceToLive'' leaves the family dog indoors on a hot summer day, forgetting the air conditioner was on a timer. By the time she gets back, the poor thing has collapsed from heat stroke and dies shortly after. It haunts her even years later.

** In ''Anime/MagicalGirlLyricalNanohaAs'', Admiral Graham blames himself for Admiral Clyde's death, as he was forced to destroy the Hestia with Clyde on board, at Clyde's insistence, rather than let the Book of Darkness take over the ship and use the [[WaveMotionGun Arc-en-ciel]] on the other ships.

** Minor character Vice also has one of these: he used to be a sniper of [[ImprobableAimingSkills quite a bit of skill]], but he now pilots helicopters. Why? Because several years back, his little sister was involved in a hostage situation. He tried to shoot her kidnapper but missed... and [[EyeScream hit her in the eye]]. Though she survived (and doesn't hold him responsible, recognizing it as an accident), he cannot forgive himself, and resolved to give up sniping.

* In ''Manga/MagicKnightRayearth'', [[spoiler:being unable to save Princess Emeraude]] is considered this for Hikaru, Umi and Fuu. Mostly because they powered through the entire adventure, thinking it was completely straightforward and never thought twice about questioning their mission. It's so bad that, in the anime, Hikaru accidentally creates her own EvilTwin.

* In the horror manga ''Presents'', Kurumi recalls an incident with a young girl whose parents would give stuffed rabbit toys as a substitute for love. Kurumi takes pity on the girl and, even though she knows better, lies and says each rabbit is stuffed with her parents' love. The next morning, however, they are anything ''but'' loving, and the housekeeper tells the girl the only reason her mother had her was to replace a pet rabbit that died. The girl violently snaps, and later that night she cuts open her parents with a pair of hedge trimmers before tearing the stuffing out of the rabbit toys and stuffing into their dead bodies. It's implied she does the same thing to the housekeeper to "share" her parents love.

* In ''Anime/SwordOfTheStranger'', Nanashi has more or less sworn off drawing his sword. What makes this interesting is that his failure is MORAL rather then Physical. [[spoiler:He executed two children, by power of peer pressure. It's hard to disobey orders when surrounded by an army. Part of a military action, it's unclear the exact circumstances but it was likely a coup d'état. Nanashi only draws his sword in the eleventh hour in a last desperate attempt to save Kotaro, who strongly resembles the boy Nanashi executed]]. [[spoiler:By BITING THROUGH THE PEACE KNOT WHILE RUNNING AT FULL SPRINT ACROSS ROOFTOPS IN THE SNOW TO THE CROWNING MUSIC OF AWESOME]].

* In ''Anime/YuGiOhArcV'', Yuzu Hiiragi is hit with this though the early episodes - the You Show School is on the line against LDS with a 3 vs. 3 match and while Yuya wins his match, Yuzu loses hers due to the fact that she's been distracted by the encounters with the mysterious boy who resembles Yuya. When Gongenzaka forces a tie, leading to Yuya and Reiji to have their first match, one that ends with a tie but Yuya takes harshly because Reiji used Pendulum Summon. She feels that, had she not been distracted, this wouldn't of happened.

** During his tenure on ''Comicbook/TheAvengers'', Creator/KurtBusiek did a good job of finally making Ultron into a credible threat, up to and including having him wipe a country's population off the map. Pym's destroying the primary unit with a metal disruptor, and a subsequent character arc that involved quite literal split personalities, were ''supposed'' to finally put Pym's demons to rest and let him start growing as a character again without the existence of Ultron and his other failures to continue hindering him. Yeah... not so much. Later writers actively regressed his sanity, brought back Ultron ''more than once'', and had him replaced by an alien who [[spoiler:tried to kill his ex before Thor accidentally turned her into a dimension, which Pym is obsessively trying to fix at the cost of his relationships with his team and Jocasta]]. As of the most recent Avengers stories, he's possibly even more screwed up now than he was then.

* ''ComicBook/{{Chassis}}'': In her first professional race, Chassis [=McBain=] is forced to take evasive action due to a dangerous maneuver by ALEX Prime. In doing so, she collides with 'Rocketman' Rodriquez; forcing him off the track. Rodriquez collides with a pylon and is killed. This event haunts Chassis throughout her career, and makes her always help racers in trouble, even if doing so causes her to lose the race.

** Parodied in a Carl Barks comic; In one story, Donald Duck, Scrooge, and the nephews learn that Gladstone Gander has ''something'' locked in a safe that he never lets anyone see. They believe it's a charm that is the source of Gladstone's uncanny good fortune, but after much pressure, Gladstone admits its anything but; it's just a nondescript dime, the only salary he has ever earned from working, which he did during an unusually long dry spell in his luck. Gladstone is so smug about his luck providing him with everything that he considers the dime to be a symbol of his MomentOfWeakness, and actually breaks down crying bitter tears as he tells the Ducks about it. (Who, BTW, are very close to caving in Gladstone's head at that point.)

* In the ''ComicBook/FantasticFour'', Reed Richards' own miscalculation and arrogance are what led to the titular team being hit by gamma rays and given superpowers. In the case of Reed, Sue, and Johnny, this is no big deal. But Ben's powers leave him a freakish rock monster, and being trapped like that put a huge barrier between the two of them for years, in spite of being best friends. It wouldn't have been so bad if Ben could just change back from being The Thing, but StatusQuoIsGod so any changes back to a human are doomed to be short-lived. The fact that Reed is responsible for his friend's condition and cannot permanently cure him is something that has weighed heavily upon him his entire career. [[spoiler:When the team finds out that their transformation was caused by the ruler of a planet who was scared of their arrival and tried to force them back, Ben goes on a RoaringRampageOfRevenge because he realized that he'd blamed the wrong guy all along. Even when Ben finally buries the hatchet with Reed, Reed himself refuses to let it go privately and resolves to protect his family better.]]
** Also from the ComicBook/FantasticFour is the supervillain Doctor Doom. Doom built a machine that would allow him to communicate with the spirit of his dead mother, and was told beforehand by Richards that it would critically fail. But when he ignored this, that's exactly what wound up happening and left his face scarred. [[NeverMyFault Years later he still can't accept that it was his fault it happened]], and [[DisproportionateRetribution devotes his life to killing Richards after convincing himself he must have tampered with the machine]].

*** Actually all this was based on John Byrne's retcon of the Lee/Kirby origin, based on an idea by Kirby that either Creator/StanLee had discarded or Creator/JackKirby only had it after the original version was published in ''Fantastic Four Annual'' #2 (1964). There, Doom's head is completely bound up and hidden beneath bandages and in the caption Stan Lee unequivocally states: "As for Victor Von Doom... his face was hopelessly disfigured!" Also on the page after that, even though the mask is not completely cooled when it is put on Doom's face, it is cool enough for the monk to hold it in his bare hands (you can easily discern his fingernails etc.) By the evidence of that Annual, all the mask likely did was singe Victor's eyebrows.
*** In a ShockingSwerve, it now turns out that Doom's disfigurement is actually Ben's greatest failure. After years, he admitted that he had purposefully sabotaged Victor's machine after seeing how badly he treated Reed, and thus was presumably the one responsible for his transformation into Doctor Doom. During ''Comicbook/AgeOfUltron'', Ben claims he's wrestled with the guilt for years, but is too terrified to tell anyone what he did.
* The plot of the comic series ''ComicBook/{{Fell}}'' is essentially watching Detective Fell right after his greatest failure, one that resulted in his banishment to his city's {{Shadowland}}, a [[UrbanSegregation ridiculously poor and crime-riden slum]]. Most of the comic so far revolves around whether the already overly intense Fell, ([[TheProfiler who may be a little too good at getting inside the head of psychos]]) [[BreakTheHaughty will snap in his exile]], get killed, or come out of it redeemed.

** Another Green Lantern, Kyle Rayner, had his mother die of an unknown fatal disease. Even when Kyle, with God-like power, tries to resurrect her, she asks to be allowed to die. During the "Sinestro Corps War" {{Arc}} [[spoiler: Sinestro reveals to a captive Kyle that her death was the work of an sentient alien virus working for the Sinestro Corps, and was all part of a plan to make him vulnerable to possession by Parallax]].

* ''ComicBook/{{Nightwing}}'' had a moment revealed following ''ComicBook/ZeroHour''. When he was Robin, it was up to him to rescue Batman and the DA that replaced Harvey Dent when he became Two-Face. When he confronted the aforementioned villain, he was planning to hang the both of them for their "crimes". Two-Face attempted to hang the DA and Robin responded by cutting the line with a Batarang. However, he didn't realize that Two-Face's MO applied to everything - he saved the DA from hanging, but couldn't save him from ''drowning''. Batman freed himself and saved the day, but the event haunted Dick until the first time he took up the Mantle of the Bat, finally making the save when confronting Two-Face again.
** Nightwing also feels guilt over not only the crippling of Barbara Gordon, but the death of Jason Todd. Both of them stemming from the fact that at the time both events happened Dick and Bruce had a falling out which resulted in Dick leaving Gotham and establishing himself as Nightwing. He has notably taken a [[BigBrotherMentor far more proactive role]] in mentoring subsequent members of the Bat-family (as well as serving as leader of the [[ComicBook/BatmanAndTheOutsiders Outsiders]] and a key ally to the ComicBook/BirdsOfPrey).
* ''ComicBook/ThePunisher'' 's greatest failure was [[DeathByOriginStory the loss of his family]], for which he blames himself as much as the mobsters who gunned them down, beliving that he should have been able to protect them. His war against criminals is as much to punish himself as it is to punish them.
** Punisher himself is considered a Greatest Failure by his on-again-off-again ally ComicBook/{{Daredevil}}, who was one of the first heroes the Punisher encountered (after ComicBook/SpiderMan) and who he is closely associated with. Daredevil regrets having been unable to pull Frank back from the brink when they met early in their respective careers, and feels obligated to at least try and stop Punisher's endless blood bath.

** Chase is still haunted by Gert's death, and has tried on at least two occasions to undo it. He also used to feel guilty about the time he apparently ran over his uncle, but then his uncle turned up alive a few years later.

** In ''Comicbook/WarWorld'' Superman blames himself because he has power to do nearly anything... but saving Krypton or his foster parents. Even when he's got the chance to save them, he failed.
** During UsefulNotes/{{the Silver Age|of Comic Books}} and UsefulNotes/{{the Bronze Age|OfComicBooks}}, Superman's biggest failure was arguably when he destroyed Comicbook/LexLuthor's protoplasmic lifeform that he created as well as causing his hair to fall out when he was trying to rescue Luthor from a lab fire when they were teens. Sure it was an accident and mostly not his fault (Luthor caused the fire and Superboy had no way of knowing what was inside at the time), but it didn't help that before the fire, Superboy jokingly said he could spy on Luthor to find out what he was working on. Luthor wrongly believed Superboy destroyed his experiment out of jealousy and dedicated his life to destroying him and proving he was better. Luthor had the scientific genius to make a cure for Kryptonite as well as unshrink Kandor, so if things had gone differently, Superman would have had a lot less problems in his life and an ally against evil as well.
** A painful one for Superman happened just after his resurrection in ''Comicbook/TheDeathOfSuperman''. After the excitement and relief of him returning from the dead, he and Lois raced off to Paris for a getaway to catch up. While he was gone, the Toyman kidnapped a bunch of kids, including the son of co-worker Cat Grant, Adam. Adam attempted to lead the other kids away, but Toyman caught them and slew them all. Superman was so distraught over this, it lead to him vowing never to take another vacation again.

* In ''ComicBook/TopTen'', Jeff Smax never really got over his failure to save a little princess from a dragon. Her handprint was permanently burned onto his chest, and would serve as a constant reminder of how big a screw up he was. Immediately after it happened, he informed the queen, and ran away. Across dimensions. To a world nothing at all like the one he came from. Even changing his name. Only after [[ComicBook/{{Smax}} a necessary return to his homeworld]], where the dragon was slayed and the handprint was erased, could he let it go, and only a little.

** ComicBook/{{Gambit}} has the fact that, to repay a debt to Mr. Sinister, he was forced to help gather a group for Sinister to execute a task--that being Remy got suckered into helping form the Marauders for the fateful massacre of the Morlocks and maiming of Angel in ''Mutant Massacre''.

* For [[NominalHero Naruto]] in ''[[https://www.fanfiction.net/s/3665921/50/ Black Flames Dance in the Wind: Rise of Naruto]]'' he has two for the price of one. Defeating a powerful demon accidentally caused a horrific attack on Konoha that resulted in scores of deaths, if not hundreds. Then dealing with said attack caused him to forget about Anko who very nearly died before she was found. Worse is that Anko was only still alive due to taking multiple blood pills to replenish her lost blood, so she was conscious for the entire day she was tortured to the point of near death. Even weeks later, Naruto is clearly tortured by his "abandonment" of Anko, at one point writing "I left her behind" on the written portion of the Chunin Exam.

* VideoGame/DragonAgeInquisition's ''FanFic/WalkingInCircles'': Solas, as per canon, considered his act of creating the Veil to be the biggest mistake of his life but by the time canon events start, he also considers what happened to Evelyn to be his ''other'' greatest failure. As he put it, he promised to save her but in the end, it was always her who saves him and she has to suffer for that, yet she has never once blamed or hated him and still choose to accept him which only further his GuiltComplex.

* In ''Film/BatmanVSupermanDawnOfJustice'', before the events of the film, [[Comicbook/{{Superman}} Clark]] has the [[Film/ManOfSteel battle of Metropolis]], blaming himself for not being able to prevent all the death and destruction that Zod and his followers caused, while [[Comicbook/{{Batman}} Bruce]] has both the death of Comicbook/{{Robin}}, murdered sometime before the events of the film by Comicbook/TheJoker and Comicbook/HarleyQuinn, and the destruction of the Wayne Finicial building in Metropolis during Zod's attack, which fuels a lot of his [[FantasticRacism hatred]] for Superman. During the film itself, Clark's greatest failure becomes [[spoiler: the destruction of the US Capitol building and the deaths of everyone inside, since he blames himself for not seeing the bomb that caused the destruction (although Comicbook/LoisLane discovers that Comicbook/LexLuthor hid the bomb behind lead, meaning that Clark ''wouldn't'' have spotted it even if he was looking for it)]], while Bruce's becomes allowing his fear and mistrust of Clark to become [[FallenHero hatred and cruelty]], allowing Lex to manipulate him and making him partly responsible for [[spoiler:Clark's death]]. However, Bruce [[MyGreatestSecondChance decides to learn from his mistakes]] and reach out to the other metahumans in friendship, bringing them together as a [[Comicbook/JusticeLeague team]].

* In ''Film/TheKiller'', Ah Jong/Jeffrey Chow felt this way after he accidentally blinded Jenny with a muzzleflash at the nightclub at the beginning of the movie and towards the child who he brought to a hospital after she took a bullet from one of the people out to kill him during the shootout at the beach.

* ''Film/ThePrivateLifeOfSherlockHolmes'' follows Franchise/SherlockHolmes on a case which he later comes to consider one of his greatest failure.

* ''Film/StarTrekIITheWrathOfKhan'': Kirk's blunder in failing to arm the Enterprise in time resulted in Khan blasting the ship nearly to hell. He came back nicely though....

* Jake from ''Literature/{{Animorphs}}'', whenever he recalls the David incident. Also the fact that Jake couldn't save Tobias from being trapped as a hawk. Even moreso, the fact that he couldn't save [[spoiler:Rachel or Tom from dying, not to mention the order to kill seventeen thousand Yeerks. Those two failures become to the entire focus of his personality for about five years]].

--> '''Bartimaeus:''' "It's two thousand, one hundred and twenty nine years since Ptolemy died. He was fourteen. Eight world empires have risen up and fallen away since that day, and I still carry his face."

* Near the start of ''Literature/DoctorSleep'' we get a glimpse of Daniel Torrance's adult life, one spent with alcohol and drugs in order to weaken the terrible visions his shining gives him. He eventually reaches the lowest point, however, when he robs a young mother of her money. For the next couple years, Danny can't forgive himself over this (the visions of the child and mother's deaths don't help), and it causes him to eventually stop drinking and settle in a town for good. [[spoiler:At the end of the book, 15 years later, he eventually decides to come clean and tells his friends about the deed... and is surprised to see that they don't give it much thought (being ex-drunkards like him, they had heard and done things just as bad)]].

* ''Literature/ForeverGate'': Hoodwink never forgave himself for allowing a rich guy to brainwash his daughter into the ideal HouseWife. It lead him to drinking which drove away his wife. Now he throws himself into harm way's way whenever Ari's in danger to make up for it.

* Numerous characters, including the titular one from the ''Literature/HonorHarrington'' series consider the events of Oyster Bay to be this for themselves, as Honor puts it, it was their job to stop things like that, and if they can't, what good are they to their people? To be fair, though, the people who did this had tech that was ''far'' better than even Manticore's, and it was specifically designed for stealth.

* ''Literature/LookingForAlaska'''s titular character [[spoiler:blames herself for her mother's death when she was a little kid, as she was too shocked to call an ambulance]]. Later in the novel, most of the principle cast (including the narrator) gets their own greatest failure when [[spoiler:Alaska dies in a drunken car accident halfway through the novel]]. The kicker? [[spoiler:The reason she was driving in the first place was because she realized she forgot it was the day her mother died and was trying to visit her mother's grave]].
* North from ''Literature/OfFearAndFaith''. At first this is just implied to be the case with him, as he tells August he only has a single regret. Later on we see what this regret is during a flashback. [[spoiler: When North was a child, he let his three year old sister go outside by herself while he was supposed to be watching her. By the time their parents got home (which was about five or ten minutes later), the girl had disappeared without a trace and was assumed dead, and [[ILetGwenStacyDie North has carried guilt over that mistake ever since then]]]].

* Twenty years before the events of ''Literature/TheSharingKnife'' books, as he faced the creatures of a powerful [[EldritchAbomination Malice]] during what became known as the Battle of Wolf Ridge; Patrol Leader Dag Wolverine lost all but three of his joint command, his left hand, his ''wife'', and [[ArsonMurderAndJaywalking the ridge in question]] in the space of an hour[[note]](the successful delaying action aspect that facilitated the death of the Malice in question was cold comfort)[[/note]]. Heroic Songs and Epic Poems have been composed since, and Patroller Dag [[TheMaidenNameDebate Redwing]] tends to slip out the back when younger generation of Lakewalkers start in on them.

** Creator/AgathaChristie did an hilarious subversion of the trope, and a very obvious TakeThat against the original Sherlock Holmes example just above. Literature/HerculePoirot, the brilliant if egotist detective, retells, at [[TheWatson Hasting's]] insistence, the story of his only failed case, which had involved a chocolate box. He then tells him to whisper "chocolate box" to him whenever he gets too pompous, adding, "I, who have undoubtedly the finest brain in Europe at present, can afford to be magnanimous." Hastings then immediately says "chocolate box." Poirot doesn't get the joke. At all.

** In ''Fall of Damnos'', Scipio keeps flashing back to an attack of Nurglite cultists, when he failed to stop [[spoiler:the daemon from possessing Chaplain Orad, thus holding himsef responsible for deaths of two of his squadmates]]. This leads him to become a perfectionist [[UpToEleven by Space Marine standards]], and when more squadmates die to the Necrons he's having trouble accepting it truly isn't his fault this time.
** In ''Veil of Darkness'', Sicarius considers Damnos his greatest failure and is fairly confident that he'll be severly punished for losing the planet. Understandable, considering its his first time he ever lost as a Captain.

** [[spoiler:Adric's death.]] Really, the loss of ''any'' companion usually wound the Doctor deeply, and has them beating themselves up for a good while afterwards.

** After the 50th anniversary special [[spoiler:has him '''''saving''''' Gallifrey in the war, rather than destroying it]], the Doctor believes he's "achieved" this in both the opening and closing stories of Series 9. In [[Recap/DoctorWHoS35E1TheMagiciansApprentice "The Magician's Apprentice"]]/[[Recap/DoctorWhoS35E2TheWitchsFamiliar "The Witch's Familiar"]], he comes to believe he is responsible for [[spoiler:setting Davros on the path that led him to create the Daleks]], but in fact [[spoiler:he's actually the reason Daleks understand the idea of mercy]]. In [[Recap/DoctorWhoS35E10FaceTheRaven "Face the Raven"]]/[[Recap/DoctorWhoS35E11HeavenSent "Heaven Sent"]]/[[Recap/DoctorWHoS35E12HellBent "Hell Bent"]], he blames himself for Clara [[spoiler:being KilledOffForReal in a SenselessSacrifice]] due to his "bad", unchecked influence on her tragically dovetailing with the fallout of several recent choices he's made. This temporarily turns him into a WoobieDestroyerOfWorlds, almost ''destroying all of space and time'' in an attempt to undo this tragedy. His return to sanity requires realizing that, among other things, it isn't his fault and thus '''''not''''' an example of this trope.

** The almost total destruction of the Targaryan dynasty under Barristan's watch drives him to seek redemption by serving Daenarys.

The case is based on the real life unsolved murder of Latonya Kim Wallace, the "Angel of Reservoir Hill", the investigation into which is covered in the book upon which the series is based. As noted in the book, the real life detective in charge of the investigation grew fixated on the case, but the epilogue stated that at time of writing he was beginning to accept it and move on.

* The title character of ''Series/{{Merlin|2008}}'' is an IronWoobie turned UpToEleven. But when he fails to heal the king and quite possibly turns Arthur away from magic forever, he very nearly crosses the DespairEventHorizon, and only stops because he's reminded that Arthur will need his support as king.

* ''Series/ParksAndRecreation'': A rare example from a comedy series, Ben Wyatt bankrupted his hometown when he was elected mayor at age 18. In present day he's incredibly cynical, cautious and spent his career working as a state auditor to make up for his past mistakes and save other towns from collapsing like his did. At one point he openly admits to Leslie that the event ruined his life and he'd love to run for office again someday but has to prove he's responsible now. With Leslie's help he gradually moves past it, but his hometown still hates him and the media frequently rip him apart over the debacle.

** [[Series/PowerRangersInSpace Andros]]. [[HurtingHero Dear Lord, Andros]]. First he loses his sister as a child [[spoiler:and she grows up to become one of the {{Big Bad}}s]], then his best friend Zhane is nearly killed during a battle and Andros puts him in cryogenic stasis to keep him alive. [[spoiler:They both get better]].

** Go Namsoon [[spoiler: he breaks his former best friend Heungsoo's leg, while him and the the rest of his gang were beating Heungsoo up as part of the process and punishment for him leaving. Heungsoo had been told by his coach that if he had serious aspirations of playing football professionally he couldn't be part of the gang any longer, but this injury meant he could no longer play]]. After this Namsoon experiences HeroicBSOD and spends a year eating, sleeping and crying.

* In ''Series/{{Smallville}}'', [[{{Superman}} Clark Kent]] has had several, including when he reversed time (a one-use only deal) to save Lana's life, only for his dad to suffer a heart attack and die at the end of the day. Also, John Corben/Metallo blames him for his turn to evil, because when Clark saved a bus from crashing, a passenger from that bus went on and murdered Corben's sister the next day. But in his opinion, his greatest failure is probably in the season eight finale [[spoiler:when a complex chain of actions lead to the death of Jimmy]].
* ''Series/TheSpy'': Israeli spymaster Dan Peleg has never gotten over allowing an extremely talented field agent get assigned to deep cover because he knew the man was too eager to please and would take excessive risks. The agent was almost immediately captured and killed. Peleg is motivated to not let history repeat itself when dealing with a similarly enthusiastic Eli Cohen.

** ''Series/StargateAtlantis''. Rodney [=McKay's=] unintended destruction of a solar system (well, five sixths) is brought up occasionally by Sheppard, though usually as a joke, seeing as the system was uninhabited.

** In "Family", Picard percieves being unable to stop the Borg from using him as part of their invasion in "The Best of Both Worlds" as his greatest failure.

** Castiel kills thousands of his brethren and assumes to role of God after consuming the souls of purgatory. He later is manipulated by Metaron to banish all the angels from heaven.

* For decades in ''TabletopGame/ForgottenRealms'', [[Literature/TheLegendOfDrizzt Drizzt Do'Urden]] had kept a vow to [[ApeShallNeverKillApe never kill another dark elf]]. However, he couldn't keep it forever, and in order to escape, had to kill one of his kin. He was guilt-wracked for this... but, in a possible subversion, not for long, as he realized it was a hypocritical vow, given that he had often seen the necessity of killing orcs, humans, goblins, duergar, wererats, and others who actually tended to be less AlwaysChaoticEvil than his own people. In addition, the primary reason he had been able to keep that vow for so long was because he had been able to ''avoid'' other members of his race for most of that time, and being able to keep a vow because you never end up in a situation where breaking it is possible doesn't mean all that much.
* In the ''TabletopGame/{{Warhammer 40000}}'' universe, the vast Imperium of Man has its own greatest failure during the end of the Great Crusade. During the beginning, it was believed that there was nothing science and reason couldn't conquer. [[EldritchAbomination And then they met Chaos...]]. Horus rebelled, the Emperor was place upon the Golden Throne, and suddenly the Imperium became very suspicious of itself. [[KillItWithFire So new measures were taken to make sure such heresy never happened again]].

** This is nothing compared to the Eldar race's greatest failure, which resulted in: 1) the destruction of their galaxy spanning empire, and the deaths of billions (if not ''trillions'') of their race; 2) the fragmenting of the race into [[TheStoic repressed ivory-tower ascetics]], [[NatureHero nature-attuned tribal agrarians]], and [[AxeCrazy blood-thirsty torture-obsessed sociopaths]]; and 3) '''the creation of one of the most powerful, and [[{{Squick}} seriously messed-up]] Chaos gods'''.
** [[EvilSorcerer Ahzek]] [[TheArchmage Ahriman]] feels a lot of guilt for accidentally transforming most of the Literature/ThousandSons into suits of AnimatedArmor when he cast the Rubric, and spends a lot of time trying to restore their humanity. The novel ''Ahriman: Unchanged'' reveals that he’s repressing and even deeper sense of guilt for failing to save his brother Ohrmuzd from dying of the [[BodyHorror flesh-change]].

* Lesovikk in Toys/{{Bionicle}} once briefly hesitated in a fight against a group of Zyglak, costing him his entire Toa Team, and driving him into a millennia spanning HeroicBSOD and WalkingTheEarth for ages.

** While Samara cannot be blamed for having daughters who are Ardat-Yakshi, Asari with a rare genetic disease that makes them addicted to murdering people by draining their life energy, she later makes it her life's mission to hunt down and destroy Morinth, the daughter who ran to preserve her freedom rather than join her sisters in isolation at a remote monastary where they learn to supress their urges and are far removed from any temptations.

* In ''Franchise/TheElderScrolls'' series' primary CreationMyth, this is the case for Auri-El, the [[OurElvesAreBetter Aldmeri]] [[NobleBirdOfPrey eagle]] version of Akatosh, the [[DragonsAreDivine draconic]] God of Time and [[TopGod chief deity]] of the Aedric pantheon. In his only known moment of weakness, he agreed to help [[TheMaker Lorkhan]] create Mundus (the mortal plane) in exchange for the privilege of being its king. However, Auri-El was disgusted with what they had created, and insisted that everything was permanently spoiled, and all they would be able to do would be to teach the elves to suffer with dignity. He went to war with and vanquished Lorkhan, then [[AscendToAHigherPlaneOfExistence ascended to heaven]] in full observance of his followers so that they might learn the steps needed to escape the mortal plane.

** In the prequel ''VideoGame/CrisisCore'', Zack's failure in capturing Genesis and preventing the [[spoiler: death of Angeal]] also fall into this category.

* Ethan Mars from ''VideoGame/HeavyRain'' believes that his his son Jason's death was his fault, and seems to suffer some degree of PTSD as a result.

* In ''VideoGame/{{Okami}}'', when [[spoiler: Waka tried to save the Celestials using the Ark Of Yamato]], he didn't realise that [[spoiler:Yami]] was on board, leading to the [[spoiler: Celestials]] getting slaughtered. It also lead to a horde of demons being [[spoiler:unleashed in Nippon]].

* In ''VideoGame/SpiritsOfAnglerwoodForest'', [[spoiler: Ezra]] feels extremely guilty for cursing his family, since he feels it robbed him and Phoebe of a normal life. So guilty, in fact, that he [[spoiler: goes deep into the woods alone to put a stop to it]]. [[FromBadToWorse It doesn't work]].

* In ''VideoGame/TearsToTiara2'' Enneads and Monomachus, first leaders of LaResistance and then of Hispania and Hamil's advisers have the same two events. First, [[ILetGwenStacyDie they had failed to protect Hamil's father and their old commander Hasdrubal]]. Second, they had both failed to see through Hamil's ObfuscatingStupidity to help him as he does his best to lessen the burden of the people of Hispania under the oppression of TheEmpire, and only thought of rebellion, going as far as planning to use Hamil as puppet.

* Real-life example with Blizzard concerning their on-going development of ''VideoGame/WorldOfWarcraft'' where they flatout stated during a Blizzcon interview that their biggest regret for the franchise was not creating Azjol-Nerub into a world zone during the ''Wrath of the Lich King'' era.

* ''VisualNovel/{{Grisaia No Kajitsu}}'': Amane and Sachi is living with this kind of regret:
** Amane: [[spoiler: When her entire class got stranded in a ravine after an accident, thing went to hell, the situation escalated until the survivors resorted to eating their dead classmates, something Amane and her best friend Kazuki not participated in, in fact Amane didn't even now they were doing that. When she and Kazuki try to escape, the crazed survivors try to chase them down and Amane is forced to leave Kazuki behind. She feels personally responsible for Kazuki's death, living the rest of her life believing she does not deserve happines.]]
** Sachi: [[spoiler: After her previously caring parents grow distant to her, being buried by work, Sachi doubles her effort both in school and home the earn their attention, but with little succes. An entire year of neglect later at her 10th birthday, her parents seemingly come around suddenly, which angers Sachi and she runs away. Just when her parents find her at the local playground, they are ran over by a truck right in front of Sachi's eyes. She convinces that it was her fault, for not being resonable, and thoughing out the neglect, this belief leads to severe mental issues for her.]]

* ''WebComic/StandStillStaySilent'': When he was thirteen, Lalli's MathematiciansAnswer in a scout report caused a group of soldiers from his military base to venture into a dangerous area and four people to be killed. The number was consisdered low in regards to the attack's violence. His older cousin reprimanded him quite harshly about it, and during the scolding implied that a single mistake from their grandmother was the reason they had left their old home to live on that military base five years before that event. In the present day, it causes Lalli to prefer fixing a mistake in finding a path while half asleep to leaving it hanging and forcing the rest of the crew to backtrack. When he couldn't find a safe path to a new campsite, he put himself into a PowerStrainBlackout to create one via clearing a tunnel full of [[PlagueZombie troll]] pods.

* ''Literature/WhateleyUniverse'': Captain Patriot of SPECTRUM once talked a a young mutant into surrendering to the MCO: the kid promptly disappeared and was never seen again, and the MCO still steadfastly denies he even existed. He will go rogue before he lets the MCO get their hands on Stacey and makes sure they know it.
* ''WebAnimation/{{RWBY}}'': Jaune Arc is hitted hard with that. He blames his own weakness and inability to stop [[StarCrossedLovers Pyrrha]] from fight Cinder as the reason why his partner and best friend dies. Not be able to recognize that Pyrrha was actually in love for him made that worse to Jaune. It takes until Volume 6 to Jaune forgives himself, but he still misses her and mourns her absence. Part of his current armor and weapons are made to honor Pyrrha's memory.

** Della Duck and the ''Spear of Selene'' was this to Scrooge. He had a made a special surprise for his niece Della to celebrate the birth of her children; a rocket known as the ''Spear of Selene''. No one knew about it because Scrooge told no one about this secret little project he had in the works. Unfortunately, Della had this knack for digging into things she's not supposed to be digging into, and to make matter worse, the rocket wasn't even properly tested. Della hijacked the rocket and took it for a ride in orbit, one which seemingly proved to be her last. Scrooge tried to guide Della through the cosmic storm, only for lightning to hit the ''Spear of Selene'', causing the rocket to lose contact with Scrooge and [[spoiler: ironically force Della to crash on the moon]]. Scrooge was willing to go as far as to bankrupt himself, trying to find her somewhere lost in outer space only for same event to likely befall his crew. The search for Della wound up costing him millions, if not ''billions'', of dollars and because it was proving fruitless, he was ultimately forced to cancel the search for Della by his staff. Until the events of ''Woo-oo!'', Scrooge had more or less become a shut-in and had never spoke to his family after what happened to Della.

** A side-story, shown as motion comics, gives Avatars Kyoshi and Kuruk one of these. Kyoshi formed the [[SecretPolice Dai Li]], which went on to assist an EvilChancellor from turning Ba Sing Se into a totalitarian city-state which carried after [[MagnificentBastard Azula]] conquered it. Kuruk wasn't a good Avatar, spending most of his time [[CompensatingForSomething impressing people with his bending prowess]]. But when he found a wife and started shaping up, [[EldritchAbomination Koh the Face-Stealer]] snatched her, possibly to punish him.

* ''WesternAnimation/OKKOLetsBeHeroes'': "Let's Take a Moment" finally reveals the whole story behind the [[NoodleIncident "sandwich incident"]] that happened between Mr. Gar and K.O.'s mom Carol: [[spoiler: Back when they were El Bow and Silver Spark, working for P.O.I.N.T., Gar had a crush on Carol, who unfortunately for him was dating fellow hero Laserblast at the time. While on a stake-out, Gar tried to confess his feelings using a sandwich as a metaphor, which distracted Carol from going to back-up Laserblast, leading to a disastrous explosion that lead to his mysterious disappearance. Not only did Carol blame Gar in the heat of the moment for distracting her, but Gar [[ItsAllMyFault blamed himself]] and resigned from P.O.I.N.T. He has been haunted by that event ever since, especially since he never got over his crush on Carol. After the events of "Let's Take a Moment", however, Mr. Gar finally seems to be moving past it.]]

* In ''WesternAnimation/StevenUniverse'' Steven considers his inability to talk down [[spoiler: Jasper, Bismuth and Eyeball]] and their subsequent fates to be his biggest failure, which he finally confronts his feelings towards in "Mindful Education".

* In ''VideoGame/FateGrandOrder'': [[spoiler: Avicebron]] feels immense shame and guilt for his actions in [[spoiler: [[LightNovel/FateApocrypha the Greater Grail War]]]] - specifically [[spoiler: [[TreacheryIsASpecialKindOfEvil betraying his master]] [[WouldHurtAChild Roche]], and [[PoweredByAForsakenChild using him as a core for his Golem, Adam]]]] - to the point where he considers it the worst thing he's ever done, and badly wants to [[TheAtoner atone]]. Unusually for this trope [[spoiler: Avicebron]] only hazily remembers the actual crime, since he's a Servant, and Servant's aren't supposed to retain memories between Grail Wars, but the fact he remembers it ''at all'' just emphasizes how bad it actually was: his crime was so severe, it permanently damaged his Saint Graph and followed him into the Throne Of Heroes - his crime was actually horrible enough to ''mar his very legend as a hero''. [[spoiler: He finds some degree of redemption by making a HeroicSacrifice: turning ''himself'' into Adam's core, and handing control over to the player so they can save the world with it]].

* Agent Carolina from Machinima/RedVsBlue is this in SO many spades over her previous [[CompetitionFreak overly-competitive]] nature to please her disconnected father so long ago, where she had a great many opportunities to drive off her self-destructive path of proving herself to Project Freelancer, with the Project itself destroying the other Freelancers' lives over time during its ruinous slog of development of its AI Fragments during the years of its activity. she definitely feels multiple ripples of this '''BIG time''' after many of her former comrades died, earning the eternal vengeance of an inferno-obsessed pyromaniac and seemingly forgets a time she accidentally killed a '''very''' dear friend of a Simulation Trooper, thus having him vengefully haunt her later on in the future and giving her a VERY '''[[WaxMuseumMorgue horrific]]''' view of what happened to the other surviving agents leftover from the disbanded Project Freelancer. She especially gives [[spoiler: a past version of herself a '''very scathing''' "talk" involving her aforementioned self-destructive victory-obsessed-self, essentially [[IHatePastMe hating on her past-self a very great deal.]] ]]

The FailureKnight has this as part of his backstory to explain why he is so devoted to his new charge. Often produces a combination of BadDreams and AnxietyDreams.

* Vaarsuvius from ''Webcomic/TheOrderOfTheStick'' is a highly intelligent elven wizard with a large ego. That ego takes a severe beating when the elf is unable to defeat a highly spell-resistant death knight, fails to prevent the hobgoblins from overrunning the breach at Azure City and winning the battle (including having fleeing allied soldiers ''beg'' him/her to help them and one of them cursing the elf's "useless goddamn magic" with her dying breath after V is unable to help them due to having run out of spells), and then spends months trying to overcome the effects of an anti-scrying abjuration without luck, in a situation when the fate of the world practically hinges on the elf's success. The long-term consequences for Vaarsuvius remain yet to be revealed, but in the short term, they certainly include BadDreams, every symptom in the book for Post Traumatic Stress Disorder, and easy temptation to a FaceHeelTurn when his/her self-perceived lack of ability puts his family in danger.

* ''Webcomic/TowerOfGod'': For Hon Arkraptor, his inability to save his daughter is what drives him to climb the Tower.