Jerkass Woobie / Web Original

A-E

• Bitey of Brackenwood is a complete ass, going out of his way to ruin the day for Brackenwood's other creatures. It is eventually revealed that he acts out of jealousy. He can't stand seeing other creatures happy with their kin, and being the Last of His Kind compounds this jealousy.
• Light in Death Note: The Abridged Series (kpts4tv). Sure he's a Serial Killer (who in this universe is killing off celebrities instead of criminals) but he's also being molested by Shinigami and the man he's fallen in love with just wants to see him executed. His Freak Out after L dies cements his Woobie status.
  • Mello is a strong candidate as well. That poor psycho had to grow up with Near! And he gets killed over a stupid misunderstanding.
  • Poor Mikami. The writer really has it in for him. [1]
  • L is ever a Grade A Jerkass but still being being Buried Alive / resurrected just to die again was not cool. Actually that was (probably) Beyond Birthday who had stolen L's identity so that also qualifies him for this trope. L himself still qualifies seeing as the real L was being kept alive in Light's basement / lovenest for the last five years. (Probably.)
• Captain Hammer, by the end of Dr. Horrible's Sing-Along Blog. He's a Jerk Jock who bullies the Villain Protagonist For the Evulz, and is only a hero because it's easier and it gets him laid. Then, at the end, we find out that, in his entire life, he's never before felt pain, and when he does, his response is to cry for his mother and run away.
  • The aforementioned Villain Protagonist - Doctor Horrible himself - counts as well. Too nervous around the women he's attracted to to tell her that he likes her, gets brutally beaten up by Captain Hammer repeatedly, but he is still a Card-Carrying Villain (not to mention his feelings for Penny can be interpreted in a less sympathetic way).
• Dragon Ball Z Abridged has a lot of jerks, but there's some that people can feel sorry for:
  • Vegeta's a horrible man to be sure, but the sheer amount of abuse he gets put through in the name of comedy earns him a few sympathy points.
  • In the Ginyu Force. They all are mercenaries who gleefully work for Freeza and do his dirty work. However…
    • Burter is revealed to be deeply insecure, believing that he has absolutely nothing that makes him unique, and just wants to be special. He claims that he's the fastest in the universe because without it, he's just "that big blue snake guy". Becomes sadder when we learn that this is why Ginyu had him on the team: a tall blue guy to balance out Jeice's short red guy.
    • Jeice becomes this after the death of his best friend Burter.
    • Guldo is looked down on by everybody and, unlike the two former, doesn't even have a friend to show him support.
  • Krillin acts insensitively towards a lot of people, but that's because the world is constantly out to get him.
  • Then there's Piccolo, who acts cold and aloof but is so insecure and desperate for friends that you kind of feel bad for him. Of course, he has Nail, but he doesn't do anything to help in the most dire of situations.
  • Cooler, who's shown to be more responsible, powerful and much less needlessly homicidal than his younger brother, yet aside from his minions is rarely given the respect he deserves, be it from the main characters or his own family. Even Goku expresses pity for him.
  • Raditz if you think about it. His father paid little to no attention, his planet was destroyed and he was treated with ridicule by his fellow remaining Saiyans, Nappa and Vegeta, due to him only being as powerful as a Saibaman. Even after he dies he still doesn't get any respect.
    Raditz: I… hate… all of you.
  • Dende. He tells Freeza the heroes are from Earth for a petty reason, turns out to be as narcissitic as Guru (Super Kami Dende) and can be a vengeful one but you can't help but feel bad for the kid who lost his family once and then got kidnapped by Goku, separating him again from his family.
  • If you aren't completely turned off by Satan's It's All About Me attitude, you may feel a little sympathy for him in a Jerkass Woobie kind of way. If Cell really was accidentally telling the truth during his brief "The Reason You Suck" Speech, Mark "Hercule" Satan used to be a homeless man who started his carrier in Bum Fights. He still managed to become a famous star nonetheless. Now, he may be an Attention Whore, but he's also Lonely at the Top and the only person who may genuinely still love him is his daughter. Then comes the Foregone Conclusion of his "fight" with Cell, and the outcome is way more graphic than in canon.
    Cell: "Do you have any actual friends? Any relationships at all that aren't about your money or your position?"
    Mr. Satan: (weakly) "I have a daughter…"
• Tommy from the Dream SMP is loud, crass, self-centered and often steals or griefs other people's belongings for fun when he has nothing else to do. He's also been involved in multiple wars at age sixteen, has his most prized possessions constantly dangled in front of his face or used as bargaining chips, been exiled from his own nation by a dictator, been forced to watch Wilbur, his surrogate brother and role model, enter an extreme mental spiral and blow up the nation they founded together before being stabbed to death by his father at his own request, been exiled again by his best friend after pressure from Dream, been manipulated and gaslit to the point of suicidality by Dream, returned to his home to find that everyone except Tubbo either does not care about him or actively hates him, then watched as his nation was destroyed again by Dream, his former ally Technoblade, and his surrogate father Philza, this time beyond repair. He was then dragged out into the wilderness with Tubbo to fight Dream, lost horribly, and almost had to watch Tubbo die in front of his eyes. Then, after finally getting a break for a few weeks, Tommy gets trapped in prison with Dream for a full week, only for Sam to come back after the week is up to tell him he has to stay there longer. When Tommy angrily tells Dream that he doesn't believe he actually has the power to revive people, Dream beats him to death, then brings him back to life just to prove that he can, inadvertently trapping Tommy in a dark, soundless void with only Wilbur and Schlatt for company for what, to him, felt like two months. Tommy might not be the nicest person, but the kid's time on the server has just been one long Trauma Conga Line.
• David of Economy Watch is traumatized and has had a difficult past, hence why he disguises his pain with jokes and a bit of an asshole personality.
• Tom of Echo Chamber. While Tom is an ass to everyone and his excuse for being so is...weak, when he actually admits why he struggles, he shows a scared side. Especially obvious in "Romantic False Lead", when Tom's reasons for loving Porn Girl is that she doesn't threaten, scare, or hurt him.

F-H

• Both Zaboo and Bladezz from The Guild. The first is a Stalker with a Crush who's just so naive and well-meaning that Codex can't figure out whether she wants to ignominiously boot him out of her life or hug him. The second is a troll and a bit of a Jerkass, but he spends much of season 3 having incredibly nasty stuff happen to him.
  • Also, Tink, although she's more Jerkass than Woobie.
  • Zaboo is creepy and horrible with people, yeah, but he doesn't qualify as a jerkass. Even when he does rude things, it's always done with the best intentions and a loving heart. He's just...super creepy. (And a complete Woobie.)
• Efeddre of Guts and Sass: An Anti-Epic has a Dark and Troubled Past where he was captured and tortured for nine years. He regularly verbally abuses the people who rescued him, but few feel like they can smack him because it's only been a year since he was rescued.
• The Green Goblin from I'm a Marvel... And I'm a DC. The poor guy is always getting beaten up (even though this is Played for Laughs) and the object of his affection is hopelessly devoted to her abusive boyfriend (the Joker). Of course, he does treat his son like garbage.

I-K

• Jiz's interpretation of Kimber. She's an annoying racist who is okay with Jiz's psychotic tendencies and even coherces a dry-ckeaning lady to be their new Aja, but she's bullied by her own sister and friends for being gay (said sister regularly has sex with women, mind you).
• Jackie from the Jerry series. In the original short, she steals from the protagonist twice. In her own short, she cheats on her boyfriend, beats the shit out of several people, and maces a guy for giving her a flower because he was ugly. And, she gets kicked out of their house, has her suitcase stolen, gets sexually assaulted, gets mugged, becomes a stripper, breaks her ankle, gets sexually assaulted by her doctor, does heroin, etc. The whole thing karmically balances pretty well.

L-O

• Tim in Marble Hornets initially comes across this way. Later on, however, the series makes sure to point out that Jay kinda earned the reactions he got, causing Tim to end up as a straight-up vanilla Woobie instead.
• Matthew Santoro:
  • It's pretty mean of Eugene to threaten Matt with a lightsaber, but he doesn't deserve being looked down upon by Matt, all for his nerdiness.
  • Hugo. It's downright evil of him to knock Matt unconscious, but he doesn't deserve being judged just for being crazy.
• The Mentally Advanced Series version of Twilight, doesn't exactly have things much better. She is a bigoted, cynical, alcoholic, jerk, who often treats her adopted brother Spike like her own personnel slave and often treats her "friends" with a mixture of contempt and annoyance, often not even trying to actually bond with them, as she's supposed. But, she was also raised by Celestia and spent her childhood going through everything from having her prized stuffed bumblebee torn open to being forced to dissect a dog, because she told Celestia she wanted a puppy. This is not only implied to be what molded her into the pony she is today, but has also left her so emotionally scared that she has a complete mental breakdown anytime she even thinks she might of let Celestia down and at one point breaks down crying after recounting the stories behind the above experiences, before asking her friends if they have any whiskey.. or paint thinner. And that's not even getting into the fact that she is the only sane mare in a land full of jerk asses and at times seems to be the only one that even slightly cares about making better future.
• The Neopets character Sophie the Swamp Witch is a grumpy Solitary Sorceress, ready to cast spells on any who dare enter her shack and bother her. Her backstory explains why she is the way she is. When she was a little girl, her brother unwittingly brought a curse upon their hometown, which caused all the inhabitants (except her) to mutate into horrific monsters. She was forced to flee into the woods to escape an angry mob, was separated from her family, and lived in isolation for years afterward, all the while desperately trying to come up with a way to break the curse of the town.
• The Nostalgia Critic. He acts like a brat, often goes annoyingly screechy when pissy, and fights with everyone. But he suffers so much from the movies he watches, gets walked all over at least once by everyone on the site, and is a good guy at heart. Exaggerated in fanfiction where he's the fandom bike, and they tend to do their very best to break him by humiliating him as much as they can.
  • The critic himself pointed this out in his editorial "Why is Loki so Hot?", in which he looks up this article to prove a point about Loki of the The Avengers' appeal. Much to his dismay, he found an entry for himself in the trope.
  • Perhaps fittingly, The Nostalgia Chick too. She's not too fond of empathy, treats BFF Nella like crap (even though Nella is a Butt-Monkey professionally, it still counts), and her reasons for trying to kill the Critic in Kickassia were purely for her own gain and had nothing to do with the others. However, she has awful self-esteem, had a shitty childhood, and there's been a few times where you can tell that she really does love her best friend.
  • Ask That Guy with the Glasses is obviously more evil than those two for reasons you can find pretty much everywhere, but he had a terrible childhood, is violently fucked up, and you kind have to feel sorry for him when he breaks down in tears for no reason. Then it gets worse when he takes his medicine, and becomes the hysterical but skin-crawlingly creepy persona. It's the better alternative than the horrible, miserable wreck of a man he'd be otherwise.
  • Upon return, and becoming an Ensemble Cast, other characters fit the trope as well; Hyper's a Tragic Villain stalker, Malice kills people for petty reasons but was sexually abused, and Evilina is daughter of the devil but Critic makes her cry from punching her in the back of the head.

P-S

• If you stretch the definition of "woobie" quite a bit, and keep in mind that "jerkass" is a gross understatement, SCP-682 could be interpreted as one.
  • Quite a few specimens fall into this and other Woobie categories... To the point that it's been put up on the "Cliches to avoid unless you SERIOUSLY know what you're doing" list. Especially if "but is really a sad person inside coping by being overly cheery" is their only flaw.
  • Adding to that, its arguable both The SCPF and GOC quality. Despite the human rights violations that both The Foundation and the GOC have and their trigger-happiness when it comes to containment and destruction respectively, both organisations have been through a lot. Between losing agents in droves, having their near limitless budgets stretched to the breaking point and the horrific circumstances that may have lead to their creations (not to mention just being in the SCP-verse) the only things scarier then them is the suffering inflicted onto them.
• Bob from Supermarioglitchy4's Super Mario 64 Bloopers may be a selfish asshole who often causes problems the others have to fix and his friends treat him like crap for this reason. But the only reason he behaves this way is because he's extremely lonely and has never felt loved.
• Bowser Junior from SuperMarioLogan Sure, he's a bratty jerkass, But his mom abandoned him, his dad acts like he never existed and loves a TV show more than him. Junior was also traumatized at military school and he sounded like he wanted to commit suicide. Bare in mind, in the series chronology, Junior is 7 years old when this all happens!! Poor Kid......
  • From his debut in "Mario The Babysitter!" onwards, Jeffy was always a rude Insufferable Imbecile who would generally annoy Mario and make his life harder, wasn't above cussing out him and Rosalina and never obeys orders. Not to mention the infamous "Jeffy's Bad Word" where he gets Mario humiliated and tortures far worse then before. Then, "Jeffy's Parents!" and "Jeffy's Sister Returns!" reveals that his childhood was terrible; he grew up with an abusive, alcoholic prostitute Gonk of a mother whose treatment of him could give Bowser's own treatment of Junior a run for its' money, who later ditched him at Mario's apartment after being fed up with him, and only agreed to take him back when his value (as in, the amount of money he'd get) was proven . Said mother also cost his sister Feebee's life by taking her helmet for an ashtray, and he had to watch his sister die in front of him. In fact, when his mom first showed up, Jeffy was terrified, begging Mario not let her take him back. With a life like this, it's no wonder why Jeffy became what he is today.
• Kirito from Sword Art Online Abridged is the best player in the game and loves to gloat about it, considers himself Surrounded by Idiots and isn't shy about telling people how stupid they are, skipped out on a boss fight against Sheeptar the Sheep King (in which twelve people died) so he could power-level his Alchemy, got involved in a murder investigation purely to prove he was right about a game mechanic, and was once able to get a group of killers-for-hire to back off by giving them business advice. He's also deeply scarred from the death of his first friend, and her last words ("It's not your fault") acts as a trigger for both a Heroic BSoD and his Chronic Hero Syndrome.

T-W

• Tales of MU is narrated by one of these, especially with regards to the prejudice and bigotry of which she is routinely the victim, but which she also routinely exhibits to others. To be fair, much of this was taught to her as she grew up by her Knight Templar grandmother. But between the Mechans, the Arkhanites, Winnie, and just about anyone who disagrees with her, she gives as good as she gets on the Jerkass front.
• Toki, she started out as this in Time Heals No Wounds II, before her redemption and change of heart. To further drive the point home, she wasn't always like that and was rather sweet, however, deep within the pain from being abused and then neglected (on top of that almost dying of cancer, after it was allowed to reach later stages) eventually poisoned her, allowing her personality to be tainted and turning her into the mentally ill intimidating wreck that she is, making sure no one could ever hurt her again and that she would be one to hurt, in control, and to be betray, just like it had happened to her. The quote below is just a summmary:

  Brownie: Toki was once a sweet shy innocent girl who only wanted to be loved, according to Jinx and Spin, but the birth of Frailine turned her shallow, cold, cruel, dominating, calculating, and worst of all, sadistic.

• From Ultra Fast Pony, Rainbow Dash. She has an obnoxious personality and likes to gloat about breaking other ponies' stuff. ("Like, OMC, I totally wrecked your house, and I'm not even gonna apologize!") She's also treated like crap by the other ponies, who are very far from being saints themselves, and she is an orphan with a Hilariously Abusive Childhood, and she wants a real family more than anything else. Other characters even note that they're (briefly) torn over how to feel towards Dash:
  Rainbow Dash: I just want to be loved for once at the gala.
  The Choir: No pony likes Rainbow Dash / Because she is annoying / But now I kind of pity her / No wait, the feeling has passed.
  • Twilight is an arrogant Know-Nothing Know-It-All jerkass, who looks down on other ponies, who she considers ignorant and abuses her adopted son/slave Spike. But, she also has the unfortunate "honor" of being mentored by Celestia, who is very heavily implied to have molested her and later banishes her to a town full of ponies who hate her to the point of having no problem casually insulting her to her face, despite the fact that she saved the world and them multiple times for jack-squat in return and to top it off, she often has to be the only sane mare in world full of crazy jerks.
  Twilight: Can I please go one day without any of you guys giving me a migraine? (Rainbow Dash crashes through her home and accidentally wrecks the place) Ok! Five minutes, can I at least have that much?
• Bitch of Worm has a Hair-Trigger Temper and has maimed and even killed people, but she had an extremely harsh upbringing; her Traumatic Superpower Awakening happened when her emotionally abusive foster mother tried to drown her dog. On top of that, her powers make her unable to interpret human social cues, which left her with No Social Skills. Her Interlude makes it clear that she's very lonely, but doesn't know how to relate to people and acts aggressively because she can't tell whether or not they're mocking her.

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