History Main / UnholyMatrimony

** According to Castle Heterodyne, Dagon Heterodyne and the Skull-Queen of Skral were an example, sending attacks as overtures of flirtation.

* Many ''VisualNovel/Danganronpa2GoodbyeDespair'' fans enjoy portraying [[BlueAndOrangeMorality Nagito Komaeda]] and [[UltimateLifeForm Izuru Kamukura]] as having this dynamic during their time as Remnants of Despair, largely due to Nagito's romantic feelings towards Izuru's former self Hajime in canon.

* Many "VisualNovel/Danganronpa2GoodbyeDespair" fans enjoy portraying [[BlueAndOrangeMorality Nagito Komaeda]] and [[UltimateLifeForm Izuru Kamukura]] as having this dynamic during their time as Remnants of Despair, largely due to Nagito's romantic feelings towards Izuru's former self Hajime in canon.

* Many "VisualNovel/Danganronpa" fans enjoy portraying [[BlueAndOrangeMorality Nagito Komaeda]] and [[UltimateLifeForm Izuru Kamukura]] as having this dynamic during their time as Remnants of Despair, largely due to Nagito's romantic feelings towards Izuru's former self Hajime in canon.

* Many "Franchise/Danganronpa" fans enjoy portraying [[BlueAndOrangeMorality Nagito Komaeda]] and [[UltimateLifeForm Izuru Kamukura]] as having this dynamic during their time as Remnants of Despair, largely due to Nagito's romantic feelings towards Izuru's former self Hajime in canon.

* In ''Fanfic/ThoseWhoStandForNothingFallForAnything'' there's Light and L when the two are ("working") together. Also Light and Takada of the variety where ''both'' are faking it for personal gain, although it's suggested that Takada does carry some affection for Light. [[spoiler:Ryuk and L]] have some of this going, too.

* [[MilesGloriosus Trixie]] and [[PrinceCharmless Prince Blueblood]] in story 2 of the ''WesternAnimation/MyLittlePonyFriendshipIsMagic'' fanfic ''Legion of Gloom''. Not only is their dating considered one of the {{Squick}}iest things in the fic ''in-universe'', their marriage ceremony is... well...

* ''Manhua/RavagesOfTime'': Sima Yi finds his match in beautiful, intelligent and equally unscrupulous Shan Wuling (who was originally out to ''replace'' the Sima clan as the political mover and shaker of the realm, and only concedes defeat when he outmaneuvers her).
--> '''Zhang Lei''': A match made in heaven... a dog and his bitch.

But if ''both'' were faking it, expect them to [[RashEquilibrium show their]] [[BeneathTheMask true colors]] at the same time. HilarityEnsues -- and [[ResetButton it's never mentioned ever again]].

** The Chaotic Masters each had a harem, composed of various villains and corrupted heroines all totally dedicated to them, [[EvenEvilHasLovedOnes with the feeling being mutual.]]
** [[spoiler: Tirek the Devourer]] and Chrysalis apparently were a couple back in the day, until she apparently dumped him (though he claims he was the one to turn on her).

%%** A romance with Dorn Il-Khan is this in the extreme, and can lead to either BashBrothers or a [[LadyAndKnight Dark Lady and]] BlackKnight match-up, since Dorn is blatantly bisexual.
%%** Romancing [[LesbianVampire Hexxat]] is a downplayed version of this. She doesn't ''seem'' very evil most of the time (especially compared to Dorn) but she ''is'' a vampire who drains the blood of the living to survive. Hexxat is also quite the flirt, not just with Charname but also with her contact Cabrina and [[EvenTheGirlsWantHer Viconia]]--both of whom are evil.
%%** [[AbusiveParents Your own parents were this]]. Your father was Bhaal, the [[GodOfEvil Lord of Murder]], who planned to either [[HumanSacrifice sacrifice]] his children or [[LetsYouAndHimFight set them on each other]] as part of a ThanatosGambit. Your mother was one of his priestesses, who was so devoted to him she ''rejoiced'' at the opportunity to give birth to and sacrifice one of said children.
* Morrigan and Demitri are presented as this in ''VideoGame/{{Darkstalkers}}'' franchise, but interestingly enough not in the original games themselves. In their home games Demitri just wants Morrigan to be his mistress i.e SexSlave due her beauty and strength as well as getting House Aensland under his thumb, whilst Morrigan is a free spirit who isn’t interested in being another addition to Demitri’s VampiresHarem and turns stone rather than let Demitri claim her as his own. In the ''Darkstalkers'' manga and aforementioned anime and ''VideoGame/CrossEdge'' however they play this straight, being genuinely attracted to each other whilst being as demonic as ever.
* In ''VideoGame/DominionOfDarkness'', simulator of the evil overlord, male player character can make one of his female lieutenants/agents his consort, which brings mechanical benefits and some new scenes. Female Temptress character can "marry" optional boss King of the Pain, instead of fighting him.
* Zigzagged with Towa and Mira in the ''VideoGame/DragonBallOnline'', ''VideoGame/DragonBallHeroes'' and ''VideoGame/DragonBallXenoverse'' games. They play this straight in the former two titles genuinely caring for each other in their pursuit of power and treat Fu as their own flesh and blood child (he does have their cells, but his birth is unclear especially given he wasn’t BornAsAnAdult like his dad). In ''Xenoverse'' however their relationship is more like master and servant with Towa only seeing Mira as a tool rather than her lover and Mira even betraying her in the sequel, though he does regret it after being beaten. Despite this change, Fu the proof of their union still shows up in ''Xenoverse 2''.

* Alice and Decus of ''VideoGame/TalesOfSymphoniaDawnOfTheNewWorld'', with the "one playing the other" thing (gender-flipped). When Decus becomes a LoveMartyr, that changes everything...
* UsefulNotes/OdaNobunaga and Nouhime in ''VideoGame/SengokuBasara''. Nobunaga is an EvilOverlord, while Nouhime is his LoveMartyr PsychoSupporter. On Nouhime's death, Nobunaga deems her worthless.
* Nobunaga and Nouhime have a similar relationship in ''VideoGame/SamuraiWarriors'' starting from the second game. (In the first, she struggled between killing him and killing ''for'' him.) Unlike the above example, this was a little smoother as Nobunaga was cordial and amused with Nouhime's attitude about him, but more or less [[InLoveWithYourCarnage they are attracted with each other's carnage lust]].

* ''VideoGame/WorldOfWarcraft'':
** Subverted with Dalliah and Soccothrates, the quarreling demon couple in Acratraz. It is highly implied that spending so long as cellmates has made them despise each other. Should the heroes focus on one of them, the other does nothing to help his/her spouse, watching while providing snarky commentary.
** Deathwing and Sintharia. However, they were only together because she was the only one of his consorts strong enough to ''survive'' the mating after his FaceHeelTurn. Also during the earliest days of the Cataclysm Beta there was datamined info that Deathwing was going to corrupt Alexstrasza the Life-Binder and together they would conquer the world.
** King Ymiron and Queen Angerboda, the leaders of the villainous Vrykul.
** Sally Whitemane and Renault Mograine, the overseers of the Scarlet Monastery. Which have a villainous LadyAndKnight vibe going on about them. As of the fourth expansion, this evolved into an AlasPoorVillain scenario. Mograine had [[spoiler:been canonically killed by his father ghost as revenge for his betrayal and murder of him (long story)]]. So Whitemane carries on as the leader of TheRemnant of the (in)famous [[KnightTemplar Scarlet]] [[HeWhoFightsMonsters Crusade]], this time with [[SuspiciouslySimilarSubstitute Commander Durand]] to replace Mograine for gameplay purposes. But what really sells it are Whitemane's [[spoiler:last words following her allegedly final defeat]]:
--->'''Whitemane''': [[spoiler:Mograine...]]
** Malygos and Saragosa. Killing Saragosa and then ''taunting Malygos over Saragosa's corpse'' earned the red dragon Keristrasza a FateWorseThanDeath at the hands of a berserk Aspect of Magic. And then death, too, in The Nexus.
* Lady and Killer from ''VideoGame/ShadowHeartsFromTheNewWorld''. Though whether the latter was actually in love or merely {{Mind Control}}led is debatable.
* ''Franchise/StarWars: VideoGame/KnightsOfTheOldRepublic'':

** With the Restored Content GameMod this is possible in ''VideoGame/KnightsOfTheOldRepublicIITheSithLords'' on a DarkSide path, although with either gender [[LoveTriangle with who]] [[MurderTheHypotenuse gets complicated]].
** ''VideoGame/StarWarsTheOldRepublic'' has this with the DarkSide Sith Warrior PlayerCharacter and his apprentice/wife [[CorruptTheCutie Jaesa Willsaam]]. There's also Darth Malgus, one of the main villains, who's happily married to a cute Twi'lek (ex-)slavegirl. The fact that he treats her like a wife rather than a slave is a source of annoyance to the largely xenophobic empire, but since he [[EqualOpportunityEvil refuses to play politics]] and spends most of his time on the Imperial Fleet fighting (and mostly winning) battles for the Empire, it's largely ignored. That, however, does not mean that their apparently genuine, two-sided love doesn't wind up with a tragic ending...
** The ''KOTORII'' GameMod ''[[FanGame Knights of the Old Republic III]]: VideoGame/TheJediMasters'' has Darths Kilorme & Iilo, members of the True Sith inner circle who lead their HumanoidAbomination shock troops known as Screamers. However, the two themselves were [[WasOnceAMan warped in a similar manner]] to them by the DarkSide, just barely retaining their sense of self, and your SpiritAdvisor Freedon Nadd questions [[EmptyShell whether they can even comprehend their own marriage anymore]].
* ''VideoGame/NeverwinterNights'':
** A possibility with Blackguard Aribeth and the player in the end of ''[[VideoGame/NeverwinterNights Hordes of the Underdark]]''.
** If you pick the evil path in [[VideoGame/NeverwinterNights2 the second game]], the player and Gann or Safiya (depending on gender). Also in the second game, before it was cut, an evil female player and Bishop.
** Certain mods do have examples, including Vico and the player in ''VideoGame/ADanceWithRogues'' and Alex and the player in ''VideoGame/TheBastardOfKosigan.''
** In the ''Shadowlords'' mod series, it's possible for an evil female character to slowly corrupt Nooble Unders, paladin-wannabe through the right dialogue choices, while the sequel series, ''Dreamcatcher'', has the option of starting a rather interesting romance with him.

** [=LeChuck=] tries to do this in ''[[VideoGame/TalesOfMonkeyIsland Chapter 5: Rise of the Pirate God]]'', [[spoiler:using his Voodoo powers from [[MacGuffin La Esponja Grande]] and the Crossroads to turn Elaine into a Demon Bride/Goddess like himself which makes her turn evil. It's all a plan by Elaine, to allow Guybrush to save her and defeat [=LeChuck=] later]].

* ''VideoGame/{{Catherine}}'': In one of the MultipleEndings, [[spoiler:[[HellHasNewManagement Vincent storms and takes over hell]], then proceeds to rule it with Catherine at his side. And yes, the two are genuinely in love and are HappilyMarried]].
* Soltier and Lapis of ''VideoGame/BlazeUnion''. This, along with the fact that they're {{Anti Villain}}s, [[RedemptionEarnsLife helps to earn them life]] in one of the game's endings. Their feelings for each other are both very mutual and very genuine.
* While not exactly the main villains, William and Annette Birkin in ''VideoGame/ResidentEvil2'' seem to be a happily married couple of scientists. {{Mad Scientist}}s!
* [[TheBrute Black Scorpion]] and [[CombatSadomasochist Silver Mantis]] seem to have this sort of relationship in ''Videogame/CityOfHeroes'' - He’s a sadist, she’ a masochist, they're both cyborgs so what others consider impalement and dismemberment they consider foreplay. Then we have [[BigBad Lord Recluse]] and [[BattleButler Red Widow]]. She assassinated his boss for him, he founded a nation of evil with her. World Domination is a relationship-goal, as far as they are concerned.
* ''VideoGame/TrafficDepartment2192'':
** Near the end of episode 3, Generals Talon and Marilith are not only lovers, but conspiring to murder the other generals, Kreel and Orlok, in contention for the position as the Overlord's successor.
* ''Franchise/MortalKombat'':
** ''VideoGame/MortalKombatII'': In Mileena's non-canon ending, she is a "secret partner" with Baraka. They both [[TheStarscream kill Shao Kahn]] and take over the Outworld, ruling it as king and queen.
** ''VideoGame/MortalKombat11'': In the original timeline of games, Sindel was forced to marry Shao Kahn and committed suicide from despair. [[VideoGame/MortalKombat3 Resurrecting and brainwashing her was used as the means for Outworld's invasion of Earthrealm.]] ''Mortal Kombat 11'' changes this. Sindel's non-canon ladder ending, several fight intros, and her role in the story expansion ''Aftermath'' all confirm Sindel was not only NotBrainwashed, but a willing accomplice to Shao Kahn's conquest of her realm of Edenia, going so far as to murder her prior husband, King Jerrod. Shao Kahn tells Kitana in the story mode that he only kept Kitana around to please Sindel. One fight intro between Shao Kahn and Sindel has him respond to a challenge to prove he hasn't become weak and pathetic with a fond "Just as I remember", and their shared chapter in ''Aftermath'' has them as an unstoppable, sincerely affectionate BattleCouple.
* Downplayed in ''Videogame/Mother3'' with Tazmily's mayor Pusher and his wife Elmore. While they are not outright evil, they are easily the two most [[{{Jerkass}} unpleasant people]] in Tazmily village. Elmore even outright tells Lucas that she and Pusher ''hate him''.
* ''Franchise/TheElderScrolls'':
** The [[OneBadMother Night Mother]] is the mysterious EvilMatriarch leader of the Dark Brotherhood, an illegal [[MurderInc assassin's guild]] with a propensity toward PsychoForHire traits in its membership who practice a ReligionOfEvil worshipping Sithis, a primeval GodOfEvil force representing chaos, change, and limitation. The Night Mother is said to be the "bride" of Sithis who, according to legend, was once a mortal woman who bore Sithis five children, then [[OffingTheOffspring sacrificed them]] to him.
** ''[[VideoGame/TheElderScrollsVSkyrim Skyrim]]'':
*** Astrid and Arnbjorn are HappilyMarried. They're also the de facto leaders of TheRemnant of the [[BrotherhoodOfEvil Dark Brotherhood]].
*** Hert and Hern, the owners of the Half-Moon Mill. They're vampires who lure unsuspecting travelers to their doom by offering them shelter for the night.
** In ''[[VideoGame/TheElderScrollsOnline Online]]'', Vaermina, the [[OurGodsAreDifferent Daedric Prince]] of Nightmares, reveals that she is in love with her champion. Her reaction to his death (at your hands) backs this up, as she [[CuteAndPsycho gleefully describes]] how she is going to spent the next century or so [[MindRape Mind Raping]] you for killing him.
* ''VideoGame/DynastyWarriors'' from 5 onwards has an example in the couple of Cao Pi and Zhenji. She is a {{sadist}}ic LadyMacbeth, he is the [[AmbitionIsEvil ambitious]], [[AnIcePerson cold]]-as-ice [[OverlordJr successor to the Throne of Wei]]. Together, they [[RankScalesWithAsskicking spread terror on the battlefield!]] Notably their affection appears genuine, in both directions. Zhenji is happy to have found a partner who can match her drive for conquest (Cao Pi being her second husband), and as for Cao Pi, Zhenji's presence is one of the VERY few things that can make him [[TheStoic show some emotion]]. They aren't as 'villainous' after the sixth game forward, but it still shows that they're not by default nice and takes things in a more proud and [[AntiHero antiheroic]] way. Interestingly, this is quite a divergence from the [[Literature/RomanceOfTheThreeKingdoms source material]], in which Cao Pi amused himself with Zhenji for a while--after killing her first husband and taking her as spoils of war--and then forced her to commit suicide when he found a new favorite. Presumably, it was decided that this [[ValuesDissonance wouldn't play well with a contemporary audience]].
* Done ''very'' humorously at the end of ''VideoGame/SuperMarioRPG''. [[spoiler:Booster proposes to Valentina in Marrymore, and she says "yes"; however, he [[RunawayBride chickens out]] for some unknown reason at the altar, causing her to chase him.]]
* Sorceress Mortis and warlock Isa in the ''Spirits of Mystery'' series. Their affections were quite genuine, as shown in the bonus chapter of ''Spirits of Mystery 4: The Silver Arrow''.
* In ''Videogame/{{Borderlands 2}}'', BigBad Handsome Jack is in an active and happy relationship with Nisha, the Sheriff of Lynchwood. He's a fascist, megalomaniacal MegaCorp dictator intent of wiping out everyone who he considers a "bandit". She's a psychopathic BloodKnight who gets off on hurting people and being hurt right back. They're a perfect match. ''Videogame/BorderlandsThePreSequel'' shows how they eventually got together if you play as Nisha, with her gradually [[InLoveWithYourCarnage becoming more and more attracted to Jack]] as he [[JumpingOffTheSlipperySlope slides down the slope]] and becomes more and more violent and ruthless. She outright admits that she's in love when Jack [[spoiler:throws his own science team out an airlock on suspicion that one of them is a traitor]]. In ''Borderlands 2'', if you end up killing Nisha in Lynchwood, Jack will admit he's kind of pissed off that you killed his girlfriend, and he's actually surprised at how angry that makes him.
* In ''VideoGame/TheSims2'', this is heavily implied with Circe and Loki Beaker of Strangetown. Loki is a MadScientist and Circe's bio says that she knows 238 different ways to make someone scream. They also have a cell-like room in the basement for Nervous Subject, who, according to their family bio, they are experimenting on.
* Lilith and Samael of ''VideoGame/TheSecretWorld''. She was a human exiled from the Garden of Eden, he was a FallenAngel, and they initially teamed up out of convenience - the outcast Nephilim using the mortal as a pawn in his attempts to achieve world domination. However, through a mixture of magic and science, Lilith rose to become Samael's equal and eventually the two fell in love and married. Over the courses of the Ages that followed, they became an eldritch OutlawCouple: Lilith the MadScientist HumanoidAbomination plaguing the world with monsters of her own creation, Samael the [[LightIsNotGood semi-divine]] OmnicidalManiac with "a passion that could extinguish civilizations"... [[spoiler: right up until their attempts to gain control of a Gaia Engine blew up in their faces.]] These days however, the couple's marriage is on the rocks thanks to Samael's decision to [[GoingNative go native]] in the human world, and the two have been made into separate menaces.
* Probably [[ThatOneBoss the most difficult boss fight]] in ''VideoGame/IllusionOfGaia'' is the one against Jack and Silvana, a married couple of vampires. Oddly, while if you defeat Silvana first Jack [[ThisIsUnforgivable rages about how he's going to take his revenge on you for killing his wife]], if you beat Jack first Silvana says she's glad he's gone.
* The girlfriend's mother and father in ''VideoGame/FridayNightFunkin'' are trying to stop the Boyfriend from dating their daughter by challenging him to singing battles. You have to battle The Father in week 1, The Mother in week 4 and both of them in a duet in week 5.

* In ''VisualNovel/UminekoWhenTheyCry'', it turns out this is the case between [[spoiler:Bernkastel and Lambdadelta]], who have similar circumstances and would both do anything to stave off boredom. The latter is rather AmbiguouslyEvil though.
%%* In ''VisualNovel/HatePlus'', [[spoiler:Ryu and Oh Eun-a]].
%%* [[LadyOfBlackMagic Caster]] and [[spoiler:Kuzuki Souchirou]] in ''VisualNovel/FateStayNight''.

* Eric Bloodaxe and Gunnhilde the witch in ''VideoGame/FateGrandOrder''. In life they perpetrated massacres and conquered kingdoms together; according to Eric's interlude quests they're still TogetherInDeath as Heroic (villainous?) Spirits.

* In ''VisualNovel/HenchmanStory'', should main character (and henchman) Stan [[spoiler:fully commit to becoming a villain, he can pursue a relationship with the supervillain Madame Scorpion.]]

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[[folder:Web Original]]

* In ''WesternAnimation/{{Bionicle}}: Web of Shadows'', King Sidorak proposes to his Viceroy, Roodaka, and she accepts. While the movie portrays this as Sidorak having genuine affection for Roodaka, [[AllThereInTheManual other story materials]] affirm the NoHuggingNoKissing nature of the franchise and explain that "marriage" is just a political union and the proposal was a power play on Sidorak's part, as [[WeCanRuleTogether sharing his throne]] would get him influence in Roodaka's homeland and hopefully slake her power-lust, keeping her out of trouble. Whatever the motivation, it doesn't work, as she realizes that [[ICanRuleAlone once she's Queen he becomes expendable...]]
* On ''WesternAnimation/CaptainPlanetAndThePlaneteers,'' [[MadScientist Dr. Blight]] and her assistant [[ArtificialIntelligence MAL]] have a weirdly flirty relationship in the early seasons, though it becomes more LikeAnOldMarriedCouple in later seasons. She has also been known to flirt with [[CorruptCorporateExecutive Looten Plunder]], though he seems ObliviousToLove.
* One episode of ''WesternAnimation/{{Care Bears|1980s}}'' had Professor Coldheart convince villainess Auntie Freeze he wanted to marry her, and asked the Care Bears for help throwing the wedding. The gullible Care Bears agreed, reasoning that anyone capable of Love can't be bad. The reason was to sneak in an organ loud enough to destroy the cloud kingdom and crash the bears down to Earth, but when Auntie figured out it was a sham, she just twisted his ear and led him off to receive punishment...

* The ''WesternAnimation/CourageTheCowardlyDog'' episode "Muriel Meets Her Match" featured a pair of married partners-in-crime named Maria Ladrones and Manuel "Mano" Ladrones. Maria looked similar to Muriel other than having black hair, darker skin, a beauty mark, reddish eyes, and different clothes, while Mano was a disembodied hand.
* On ''WesternAnimation/{{Cyberchase}}'', Hacker and Wicked have an on-again, off-again partnership. They seem to be genuinely attracted to each other, but they'll also stab each other in the back the moment they think they can get away with it.

** Johnny 13 and Kitty; though Johnny's not the most faithful boyfriend.

--->'''Skulker''': Now that just plain hurts...

** "The Ultimate Enemy" reveals that [[EvilChef Lunch Lady]] and [[FutureBadass Box Ghost]] have a KidFromTheFuture together: Box Lunch. Team Phantom is heavily squicked out by this.
* ''WesternAnimation/DuckTales2017'': Flintheart Glomgold tries to invoke this with Goldie O'Gilt in "The Golden Lagoon Of White Agony Plains!", but Goldie has more interest in keeping their VillainTeamUp strictly professional.

* [[EvilTwin Anti-Cosmo and Anti-Wanda]] on ''WesternAnimation/TheFairlyOddparents''. Possibly also a subversion, as Anti-Cosmo doesn't seem to be particularly happy in the arrangement.
-->'''Cosmo:''' ''[moments before undergoing a potentially fatal transplant with Anti-Cosmo]'' If I don't make it, [[BewareTheSillyOnes stay away from my wife!]]\\

** Same deal for Demona and Thailog, until they broke up. (The relationship cracked when he threatened her daughter -- and shattered completely when he revealed he had a concubine cloned from her.)

* Destro and The Baroness from ''WesternAnimation/GIJoeARealAmericanHero''. They had a rather established relationship by the third miniseries and in the comics, they had been together since before they joined COBRA. In the comics, whenever one has been in serious danger, you'd best be prepared to get out of the way of the other because they will stop at NOTHING to ensure each other's well being.
* ''WesternAnimation/HouseOfMouse'' has "Halloween with Hades," an episode where [[WesternAnimation/{{Hercules}} Hades]] is trying to get the attention of fellow villain [[WesternAnimation/SleepingBeauty Maleficent]]. While he does succeed at the end of the episode (after finally losing his temper on Mickey for all the bad advice the Mouse gave him) there's no real plot or continuity in this show and they're never seen together again.

** In an episode, Dr. Drakken manages to charm [=DNAmy=] into cooperating with him. While Amy seems remarkably responsive to his cheap pickup lines, the most ''interesting'' thing about this single-episode teamup is probably that Shego seems to be downright jealous...

* ''WesternAnimation/OKKOLetsBeHeroes'': Starting in the episode "We're Captured", Lord Boxman begins courting Professor Venomous. [[spoiler: They later move in together, forming a [[BlendedFamilyDrama blended family]], and are seen wearing wedding rings in the finale, hinting that they got married.]]
* ''WesternAnimation/TheOwlHouse'': While it's clear that Odalia [[HenpeckedHusband wears the pants in their relationship]], Alador and Odalia have a surprisingly functional marriage (it's even implied during a flashback that [[HighSchoolSweethearts they've been together since their school years]]). He makes the weapons she sells, her social graces make up for his lack of tact, and she genuinely praises his abomination-making skills a few times. Too bad they're both AbusiveParents and ruthless, money-driven, image-obsessed, and [[BlueBlood blue-blooded]] arms dealers.
** Ultimately averted by "Clouds on the Horizon". [[spoiler: It's made clear their relationship is strained as Odalia only seems to view Alador as a business partner instead of a romantic one, and when her lack of ethics go too far, Alador quits and sides with their children over her.]]

** An episode features [[MadScientist Doofenshmirtz]] dating a woman just as evil as he was. [[https://www.youtube.com/watch?v=7jv1Zw5FwRg They even got a song together]], though the relationship unfortunately doesn't work out, thanks to [[HoistByHisOwnPetard Doof's Evil Plot of the Week coming back to bite him in the butt]].

* Chief from ''Animation/{{Pucca}}'', head of the local QuirkyMinibossSquad, has a crush on Garu's enemy Tobe. In one episode they became this trope after Tobe got [[LovePotion hit by one of Cupid's arrows]], and they had a little love montage showing them robbing stores together and so on. In fact, before the stuff wore off they were this close to getting married (The trope name is even used).

* In ''WesternAnimation/SouthPark,'' UsefulNotes/SaddamHussein and {{Satan}}, though most of their in-series appearances are after they break up. See above in "Films--Animated".
* Mac and Molly Mange of ''WesternAnimation/SwatKats''. They were powerful gangsters and married before they [[TookALevelInBadass died the first time]] and when they came back as robots, they quickly cheered over their new strength, durability and firepower. Yeah, they bickered a lot, but when one of them got hurt, you can bet your aft that the other would drop everything to save them.
* In the ''WesternAnimation/TransformersAnimated'' episode Society of Ultimate Villainy, a new villain shows up called Slo-Mo, who can slow things down. She apparently also can reverse aging, as she did with Nanosec. She and Nanosec flirt with each other throughout the episode. Swindle stealing Slo-Mo's timepiece (the source of her power) is a definite KickTheDog for Swindle. Interestingly, they subvert the gender dynamic mentioned at the top of the page: while they act as equals, Slo-Mo is far more important to the episode's plot.

* ''WesternAnimation/TheVentureBros'': The previous trope image was The Monarch and Dr Mrs The Monarch from The Venture Bros. Professional villains with one of the strongest relationships in the show.
* ''WesternAnimation/VoltronLegendaryDefender'' has [[spoiler: Zarkon and Honerva, aka the witch Haggar. [[PlayingWihATrope Played with]] as, until the Season 3 finale, she didn't even remember they were married]].
* [[DefiedTrope Defied]] in ''WesternAnimation/WanderOverYonder''. [[OmnicidalManiac Lord]] [[BigBad Dominator]] has no intentions at all to return the romantic feelings of [[EvilOverlord Lord]] [[BigBadWannabe Hater]]. After Dominator sets the record straight in "My Fair Hatey", Hater loses his feelings for her and instead becomes [[EvilVersusOblivion intent on stopping her from destroying the galaxy]].
* Some [[PeripheryDemographic older fans]] of ''WesternAnimation/WildKratts'' sense a bit of BelligerentSexualTension between [[RichBitch Zack]] [[EvilGenius Varmitech]] and [[TheFashionista Donita]] [[CruellaToAnimals Donata]]; they even went out on a date [[ShipTease in canon]]. Although, if there ''is'' any actual attraction, it seems [[AllLoveIsUnrequited one-sided]] on Zach's part.

* In ''WesternAnimation/XiaolinShowdown'', it was [[ShipTease highly]] [[UnresolvedSexualTension hinted]] that [[MagnificentBastard Chase Young]] and [[DarkActionGirl Wuya]] were this.

* ''Fanfic/TheChaoticMasters'': The Chaotic Masters each had a harem, composed of various villains and corrupted heroines all totally dedicated to them, [[EvenEvilHasLovedOnes with the feeling being mutual.]]

*** The ComicBook/RedSkull's daughter Sin and her lover Crossbones (one of the Skull's henchmen).
*** Viper, a high-ranking and sometimes leader of ComicBook/{{HYDRA}}, and [[Characters/{{Wolverine}} Silver Samurai]], a HeelFaceRevolvingDoor (but mostly villain). The two were briefly in an arranged marriage, but really did love each other. Viper still laments that things didn't work out. The Red Skull was briefly involved with the Viper, attracted to her nihilism as well.

*** The U-Foes, an EvilCounterpart to the ''Comicbook/FantasticFour'' (though oddly not Fantastic Four enemies), naturally also included an evil version of the Richards couple: Vector and Vapor.

** ''ComicBook/ThePunisher'': During [[ComicBook/{{Daredevil}} Stilt-Man]]'s funeral, it's revealed that he and Princess Python from the Circus of Crime had been married. Later ''Punisher'' arcs showed that Princess Python tends to do this... she's been married many times, ALWAYS to another supervillain, most recently the Gibbon.

*** Kraven the Hunter is married to a woman named Sasha, and they have three kids. The entire family shares Kraven's crazy hunter tendencies, and conspired to resurrect him in ''ComicBook/GrimHunt'' after his death in ''ComicBook/KravensLastHunt''. [[UnwantedRevival Kraven was not happy]], which led to the family's dissolution as he killed Sasha and forced his kids to hunt each other.
*** Another Spider-Man villain, Comicbook/{{Carnage}}, had a very close relationship to fellow sociopath Shriek. This is elevated to be a literal case of the trope in their live-action debut in ''Film/VenomLetThereBeCarnage'', where they were childhood delinquent sweethearts, and once Carnage breaks Shriek out of prison, they plan to get married - while killing Eddie Brock, Venom, and the cop who shot Shriek's eye in the ceremony.

*** ComicBook/{{Mystique}} was in a long loving relationship with fellow brotherhood member, Destiny, before they got separated by the latter's death. Mystique even refers to Destiny as her "wife" in [[ComicBook/AgeofXMan House of X]]. It's unclear if this is meant as a term of endearment or if they got legally married at some point during their long history together.

** From the always reliably warped ''Comicbook/DoomPatrol'', we have a rare gay example: The Brain, a disembodied brain who occasionally has a robotic body, and his [[TheDragon Dragon]] Monsieur Mallah, a hyperintelligent French [[StealthPun Marxist gorilla]].

* ''WesternAnimation/TheLegendOfVoxMachina'' has Sylas and Delilah Briarwood, mass-murdering tyrants who are working towards realizing their patron's evil plans of world domination. But the two of them are also shown to be deeply in love with one another. In fact, Delilah made the bargain with their otherwordly patron in the first place because it was to save her then-terminally-ill husband's life by turning him into a vampire. [[spoiler:When Sylas dies at the hands of Grog and Keyleth [[LightEmUp holding Sylas in a beam of holy light]], Delilah voices a cosmos-tearing shriek of outrage and despair. In her grief, Delilah attempts to summon The Whispered One to bring Sylas BackFromTheDead. But Delilah is KilledMidSentence before she can do so, rendering them both KilledOffForReal]].

* Sylas and Delilah Briarwood from ''WesternAnimation/TheLegendOfVoxMachina'' are mass-murdering psychos who are working towards realizing their supernatural patron's evil plans of apocalyptic world domination. But they're also in love, supportive, and absolutely loyal to each other. In fact, that's why Delilah made her bargain with their otherwordly patron in the first place: [[spoiler:to save her then-terminally-ill husband by turning him into a vampire. When Sylas dies permanently at the hands of Grog and Keyleth [[LightEmUp holding Sylas in a beam of holy light]], Delilah voices a cosmos-tearing shriek of outrage and despair. In her grief, she attempts to summon The Whispered One to bring Sylas BackFromTheDead. The only reason this fails is because Delilah is KilledMidSentence before she can finish summoning the Whispered One to try it]].

* Sylas and Delilah Briarwood from ''WesternAnimation/TheLegendOfVoxMachina'' are mass-murdering psychos who are working towards realizing their supernatural patron's evil plans of apocalyptic world domination. But they're also in love, supportive, and absolutely loyal to each other. In fact, that's why Delilah made her bargain with their otherwordly patron in the first place: [[spoiler:to save her then-terminally-ill husband by turning him into a vampire. When Sylas dies permanently at the hands of Grog and Keyleth, Delilah voices a cosmos-tearing shriek of outrage and despair. Iin her grief, she attempts to summon The Whispered One to bring Sylas BackFromTheDead. The only reason this fails is because Delilah is KilledMidSentence before she can summon the Whispered One to try it]].

* Sylas and Delilah Briarwood from ''WesternAnimation/TheLegendOfVoxMachina'' (which was based on campaign 1 of the live-play ttRPG webshow ''WebVideo/CriticalRole'' mentioned above): total mass-murdering psychos who are working towards [[spoiler: realizing their supernatural patron's evil plans of apocalyptic world domination]], but also in love, supportive and not even slightly toxic within their relationship, and absolutely loyal to each other. In fact, that's why Delilah [[spoiler: made her bargain with their otherwordly patron in the first place: to save her terminally ill husband by turning him into a vampire.]] Though considering [[LadyOfBlackMagic the heavily necromantic flavor of her magic spells]], the fact that [[spoiler: non-evil resurrection magic exists in this setting and they were wealthy enough to afford paying a temple for it, but Delilah didn't wait to try this option first, which implies that she thought no good- or neutral-aligned deity would ever help her]], and the fact that in the end she behaves more like [[spoiler: a fanatic cultist than someone who just has a rational interest in fulfilling her side of the bargain she made with a powerful supernatural entity]], she probably was already quite evil before she started [[spoiler: working for The Whispered One.]] But Sylas could very well have been just some random guy who was the handsome trophy husband of a powerful and wealthy wizard (WordOfGod says Delilah held a high-level position in a politically influential wizard organization back in their home country), since the general [[TabletopGame/DungeonsAndDragons D&D rules]] say that being turned into a vampire inevitably destroys your humanity and thus [[AlwaysChaoticEvil changes your character alignment to evil]], and Sylas certainly does not care about anyone but Delilah now that he's undead. This is a rare version of this trope where the female half of the couple is the more important character, as it's Delilah who's the driving force behind the couple's plans and years-long machinations - and ''not'' just in the classic LadyMacBeth sort of way, despite her SilkHidingSteel mannerisms and sub-chic choker necklace compared with Sylas' imposing physical appearance and dominating mind-control powers. It's not even really a case of BehindEveryGreatMan, since they're presenting as equals in public and in private Sylas comes across more like a "happy wife, happy life" sort of guy who's just along for the ride and acting as Delilah's [[TheDragon muscle / enforcer]] (though if it's not clear that it would be an easy win for him or they've been cornered without any other choice, Delilah won't even risk sending her beloved hubby into battle), but who would probably be equally content to simply settle down with his wife in some remote castle and be left alone by the world.

* ''Fanworks/FromRussiaWithLove'' is a ''Webcomic/{{Lackadaisy}}'' fan fic wherein Mordecai and his new partner, Innochka, strike up a close friendship that eventually turns romantic. Considering how cold and unfeeling Mordecai is, seeing Innochka draw him out of his shell and the warmth that blossoms between them is very sweet and charming. Except they're murderous borderline sociopaths bonding while carrying out brutal hitjobs for their respective employers. ObsessivelyOrganized Mordecai even sighs happily when he sees how efficient Innochka is at dismembering corpses for immolation. (She grew up butchering pigs.)

* In ''VideoGame/DominionofDarkness'', simulator of the evil overlord, male player character can make one of his female lieutenants/agents his consort, which brings mechanical benefits and some new scenes. Female Temptress character can "marry" optional boss King of the Pain, instead of fighting him.

* In ''WesternAnimation/SouthParkBiggerLongerAndUncut'', {{Satan}} is in a gay relationship with UsefulNotes/SaddamHussein, though the later is negligent and at times verbally abusive while Satan is [[TheDevilIsALoser sort of a loser]]. By the end it's quite clear that Saddam's main concern is that the coming Apocalypse will allow him to get back to Earth and conquer it for himself; with some prompting from Kenny, Satan finally snaps and kills Saddam.

*** In ''ComicBook/WonderWoman1987'' ComicBook/{{Circe}} plays a MemoryGambit in order to get close to ComicBook/{{Ares|DC}} without him realizing it's her, since even she thinks she's the AmoralAttorney Donna Milton. As Donna she grows to honestly trust and love Ares and they have a child together before the relationship goes south.

* Chelsea and Afton in ''{{Fanfic/Luminosity}}'' take part in many of the Volturi's worst atrocities, and like all vampire couples, they're unbreakably devoted to each other. (Though that's not to say they have a ''healthy'' relationship; her first move upon meeting him was to use [[MindRape her power]] to cut away his bonds to his human family so he'd [[GreenEyedMonster have no one to love but her]].)

** The U-Foes, an EvilCounterpart to the ''Comicbook/FantasticFour'' (though oddly not Fantastic Four enemies), naturally also included an evil version of the Richards couple: Vector and Vapor.
** The Absorbing Man and Titania were married. Absorbing Man left her because Titania couldn't let go of her fixation with ComicBook/SheHulk but they have since then got back together.
** During the [[Comicbook/{{Infinity}} Infinity]] event, we are introduced to Corvus Glaive and Proxima Midnight, two members of ComicBook/{{Thanos}}' Black Order who are HappilyMarried. They are shown to be supportive of each other both [[BattleCouple on]] and [[SickeninglySweethearts off the battlefield]]. If not for their roles as Thanos' [[HeroKiller Generals]] and love of [[BloodKnight killing]], they would be the rare non-dysfunctional married Marvel couple.
** ComicBook/FantasticFour villains the Mole Man and Kala (both rulers of subterranean realms, incidentally) have had a relationship that has been rocky and tumultuous. They have been married and divorced more than once, and Kala has betrayed him at least once. When last seen, they seemed to have reconciled, at least for now.
** The ComicBook/RedSkull's daughter Sin and her lover Crossbones (one of the Skull's henchmen).
** During Stilt-Man's funeral, it's revealed that he and Princess Python from the Circus of Crime had been married. Later ''Punisher'' arcs showed that Princess Python tends to do this... she's been married many times, ALWAYS to another supervillain, most recently the Gibbon.
** ''ComicBook/{{Runaways}}'' features the Pride, a criminal syndicate formed of ''six'' married couples, all of whom appear to genuinely love each other while sacrificing teenagers and ruling the Los Angeles underworld with an iron fist.
** Viper, a high-ranking and sometimes leader of ComicBook/{{HYDRA}}, and [[Characters/{{Wolverine}} Silver Samurai]], a HeelFaceRevolvingDoor (but mostly villain). The two were briefly in an arranged marriage, but really did love each other. Viper still laments that things didn't work out. The Red Skull was briefly involved with the Viper, attracted to her nihilism as well.
** {{ComicBook/Mystique}} was in a long loving relationship with fellow brotherhood member, Destiny, before they got separated by the latter's death. Mystique even refers to Destiny as her "wife" in [[ComicBook/AgeofXMan House of X]]. It's unclear if this is meant as a term of endearment or if they got legally married at some point during their long history together.
** ''ComicBook/SpiderMan'''s Kraven the Hunter is married to a woman named Sasha, and they have three kids. The entire family shares Kraven's crazy hunter tendencies, and conspired to resurrect him after his death in ''ComicBook/KravensLastHunt''. [[UnwantedRevival Kraven was not happy]], which led to the family's dissolution as he killed Sasha and forced his kids to hunt each other.
** Another Spider-Man villain, Comicbook/{{Carnage}}, had a very close relationship to fellow sociopath Shriek. This is elevated to be a literal case of the trope in their live-action debut in ''Film/VenomLetThereBeCarnage'', where they were childhood delinquent sweethearts, and once Carnage breaks Shriek out of prison, they plan to get married - while killing Eddie Brock, Venom, and the cop who shot Shriek's eye in the ceremony.
** X-Men villains Vulcan and Deathbird entered a relationship and overthrew the rulers of the Shi'ar. While it was initially in part because each found the other useful, they did grow to genuinely love each other, and Vulcan is ''pissed'' when she is hurt.
** Corvus Glaive and Proxima Midnight, the two leaders of ComicBook/TheBlackOrder. They're both the adopted children of Thanos, and slaughter ''entire species'' as a day job and revel in it. They both also deeply love each other, and Proxima is ''devasatated'' when she thinks Corvus might die (he can survive as long as his glaive does). The two border on SickeninglySweetHearts, because they're always complimenting each other's carnage.
** There is perhaps the biggest and baddest example of this trope yet in the Marvel Universe brewing between long established villains, ComicBook/{{Thanos}} and ComicBook/{{Hela}} as of ''Unworthy Thor #5''. A disguised Hela had previously helped Thanos escape from his earthly prison and she also bargained to obtain for him Ultimate Thor's version of Mjolnir if he paid her a favor in return. When she was ultimately unable to retrieve the mighty hammer from the Odinson, she killed two of Thanos' top enforcers (Proxima Midnight and Black Swan) to prove her power and then offered to give him [[DeathSeeker everything he had ever wanted]] in return for him helping her take back her kingdom, upon which the two shared a passionate embrace. Writer Jason Aaron has promised that we will see more of them getting up to no good together in the future.

* Bibok and Calosta in Creator/EstherFriesner's ''Literature/MajykByDesign''. On Orbix, Majyk is a psuedo-sentient tangible substance that actually provides the power behind spells. Our hero Kendar may have scads of Majyk, but the two of them together are positively dripping with it. Married wizards and sorcerers have a time getting divorced if their Majyk doesn't want to separate. [[spoiler:This is taken care of during the final fight when Kendar's ex-wife pretends to have had an affair with Bibok. Calosta proceeds to turn him into a variety of amusing shapes until finally he's turned into a rat which Scandal, Kendar's talking cat, eats, thereby gaining his share. Calosta was winked out of existence by Kendar's Aunt Carageena (Or was it Glucosia?) when her Sacred Eye of Delbert paperweight slipped out of her hands and struck Calosta in the chest. They didn't realize that the paperweight was, in fact, the actual artifact.]]

* ''WesternAnimation/MoralOrel'': [[spoiler:Clay and Ms. Censordoll]], at first competing in office, end up making out with each other at the end of "Nesting." They share a mutual infatuation with eggs, the former due to his [[spoiler:OedipusComplex]] and the latter due to [[spoiler:having been "castrated" as a child]].