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->'''''Poison Ivy''': Once you have frozen mankind, these babies will overrun the globe, and we shall rule them, for we will be the only two people left in the world.''
->'''''Mr. Freeze''': Adam and Evil.''
-->--''Film/BatmanAndRobin''
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%% One quote is sufficient. Please place additional entries on the quotes tab.

You know how the story goes, right? The BigBad meets TheBaroness, TheBaroness meets the BigBad, their eyes meet, and horribly discordant music that sounds not unlike the screaming of tortured souls arise. It's black magic... a match made in hell!

Lord Worldbreaker and Lady Firestorm are, individually, serious threats to the heroes, but what happens if they're suddenly working ''intimately'' together? That's when it gets ''really'' dangerous. A pair of villains capable of channeling ThePowerOfLove is enough to give even the most hardened group of heroes a serious challenge, and worse yet, [[EvilVirtues seeing the villains in love]] may make them doubt their own motivations. Should one of the villains fall, the other one grieving over their fallen lover is quite likely to initialize an AlasPoorVillain scenario, and maybe even a MyGodWhatHaveIDone. Should another villain start messing with the happy couple, it's usually played as a KickTheDog moment.

...of course, these people ''are'' villains, so you can never really be sure that one or both of them isn't just playing at being in love, in order to manipulate and use the other. If the love was genuine but unrequited, expect the one who [[LoveMartyr genuinely loved to sacrifice their life to protect the other]], only for the other to disdainfully ignore them as they lay dying, proclaiming that they're [[YouHaveOutlivedYourUsefulness no longer useful.]] Usually this signals a crossing of the MoralEventHorizon.

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 most classic version of this trope occurs when two previously established antagonists suddenly take a newfound interest in each other, but it can also involve a newcomer falling for an established villain, or even a pair of villains who were, from the beginning, a 'villainous couple'. In the first-mentioned scenario, EnemyMine may occur in order to match the united power of the couple - which can get particularly interesting if the 'bedfellow' is another villain, who is driven by jealousy...

May form a BigBadDuumvirate.

Compare VillainousFriendship, when the two are truly friends with each other, but not in a romantic way. Contrast MinionShipping (which involves minions instead of actual villains) and MadLove (which is one-sided). OutlawCouple is the petty crime version of this. In the case of fiction with [[RoguesGallery multiple villains]] where taking two out of the equation would still leave a bunch of bad guys, if it's genuine on both sides this can be used as a prelude to a HeelFaceTurn or at the very least a GetOutOfJailFreeCard. If the couple in question is heterosexual, [[NeverASelfMadeWoman expect the man to be the more important half of the couple]], possibly making her more of a DarkMistress.

Subtrope of EvenEvilHasLovedOnes. Not to be confused with AwfulWeddedLife, which describes the ''marriage itself'' to be terrible; not the couple in question.

[[noreallife]]
----
!!Examples

[[foldercontrol]]

[[folder:Anime and Manga]]
* In ''{{Mai-HiME}}'', Miyu and Alyssa make a nice couple - so loving towards each other that Mai at first has a hard time believing that they're actually villains. This plays with the trope heavily; it's not a sexual relationship, though it's definitely a loving one, [[spoiler: Alyssa's a {{Tykebomb}} rather than a true villain, and Miyu simply believes in MyMasterRightOrWrong.]]
* Sensui and Itsuki from ''YuYuHakusho'' are a rare [[HoYay homosexual]] example. Well, [[SplitPersonality sometimes]]...
** [[TokenEvilTeammate Hiei]] and [[AntiVillain Mukuro]] seem to have this going by the end of the manga.
* Kunzite and Zoisite in ''Anime/SailorMoon''. Homo or hetero, [[ShesAManInJapan depending on version]].
* In ''Manga/DeathNote'', there is Light and Misa. Just what the AntiVillain needs: A [[PsychoForHire Psycho Who Works for Free]]. Then there's Kiyomi Takada. She and Misa have a little subtext argument about who's really his lover. As Near said "Light is popular with the ladies."
* X and Ai in ''MajinTanteiNougamiNeuro'', a psychotic shapeshifting serial killer and his best friend and lover the terrorist.
* In ''RurouniKenshin'' Shishio Makoto and Yumi have a bit of a subversion on this. Yumi legitimately loves Shishio... [[spoiler: When Yumi throws herself between Shishio and Kenshin during their battle to beg them to stop for Shishio's health, Shishio uses it as an opportunistic attack to stab THROUGH her to wound Kenshin. This appalls the good guys and Kenshin is horrified. Shishio calmly tells them that they don't understand since he and Yumi knew this would happen, and Yumi declares that she's happy she could help Shishio fight for once since she always was pissed off for being a NeutralFemale. He then [[DiedInYourArmsTonight holds and comforts her while she dies]] and begs him to not lose... because ''he'' really loved her too - just enough to use her. But it's all good, sort of: after he perishes, they meet up in the afterlife and plan to [[LikeABadassOutOfHell take over hell together]]. Along with Shishio's devoted BattleButler; he lights up at the thought of going into Hell if it means serving his master.]]
* In ''OvermanKingGainer'', Siberian Railroad [[CorruptCorporateExecutive executive]] Yassaba Jin and his [[TheDragon dragon]], Adette, are very much in love, and actually make a pretty cute couple. Indeed, Jin's [[AuthorityEqualsAsskicking combat-prowess]] [[ThePowerOfLove goes up noticeably]] when he's fighting to prove himself to Adette, rather than just for corporate objectives...
* Riful and Dauf in ''{{Claymore}}'' are this. While she constantly berates him and threatens to leave him, when push comes to shove it becomes clear that they ''do'' genuinely love one another. A side story reveals, at least for Dauf, it was LoveAtFirstSight.
* Khyron/Kvamzin Kravshera and Azonia/Laplamiz from ''{{Macross}}'' / ''{{Robotech}}''.
* [[spoiler:Claire and Chane]] from ''[[LightNovel/{{Baccano}} Baccano!]]''. They actually end up quite HappilyMarried.
** Marriages between the morally questionable appear to be genetic, as [[spoiler:Chane's father Huey]]'s one and only true love was a misanthropic serial killer, [[spoiler: Monica Campanella.]]
** A joke ending in the DS game has [[spoiler:Claire]] wind up in a just as happy - and [[InterplayOfSexAndViolence far more depraved]] - marriage with ''[[spoiler:[[AxeCrazy Ladd]] [[CrackPairing Russo]]]].''
** Debatably, Isaac and Miria also qualify -- though they're more in the PluckyComicRelief AntiHero role than anything else.
* ''FlameOfRecca'' has Mokuren and Mikoto. They're quite happy until she gets wounded and he decides to just kill her ForTheEvulz. She probably should have known better.
* ''Anime/CodeGeass'' gives us [[spoiler:Emperor Charles vi Britannia and his not-so dead wife Lady Marianne]] who are very much partners and crime, in love with each other, and evil.
* In ''Manga/{{Shigurui}}'', there's Lady Iku with Seigen to whom she is completely devoted to. It is unclear how much Seigen cares about her, although he does treat her much better (ie. like an actual human being) unlike her previous lover Kogan.
* In ''Manga/KagerouNostalgia'' EvilOverlord Kiyotaka Kuroda appears to have his wife, Yasha, and his son, as {{Morality Pet}}s. As the series progresses though, it becomes increasingly apparent that Yasha is every bit as manipulative and cruel as her husband (and he knows it) and their son is ''both'' of their MoralityPet. Rikimaru would really love to be this with [[spoiler:his {{Gender Bender}}ed {{Co Dragon|s}} and {{Heterosexual Life Partner|s}} Ranmaru]].
* Kriem and Jake Martinez in ''Anime/TigerAndBunny''.
* [[BigBad Dio Brando]], a century-old vampire and [[WellIntentionedExtremist Enrico Pucci]], a morally ambiguous catholic priest make up for a very interesting case in ''Manga/JoJosBizarreAdventure''. Although it's still controversial if they are this or [[VillainousFriendship villainous friends]], the author himself has lately confirmed Dio to be [[BiTheWay into both men and women]].
* Subverted in ''FushigiYuugi''. [[RescueRomance Soi loves Nakago]], but he doesn't ''seem'' to reciprocate (although he does use her DeusSexMachina to heal, and ''generally'' treats her pretty nicely for a BigBad of his caliber). However, [[spoiler: Soi gets killed in battle, and Nakago carries her corpse around. Make of that what you will.]]
* Hansel and Gretel from ''Manga/BlackLagoon''. Despite being underage [[BrotherSisterIncest siblings]], their relationship is [[EvenEvilHasLovedones the only humanising thing about them.]]
* Hunt and Sarah from ''TegamiBachi''.
* ''Anime/TonoToIssho'': OdaNobunaga fell in love with Nohime because she was prepared to stab her father in the face without hesitation.
* In ''Manga/PuellaMagiOrikoMagica'', the villains behind the magical girl murderers are [[spoiler: Oriko and Kirika]], who have at least a strong RomanticTwoGirlFriendship, but more likely a couple. Especially since one's a LoveFreak and [[BerserkButton very sensitive]] [[{{Yandere}} about the subject]]. Even more so, [[spoiler: they end up TogetherInDeath.]]
* Barbara and Lotten, the two antagonists of the Crashtown Arc in ''Anime/YuGiOh5Ds'', and clearly two of the most vile villains in the series, only officially married in the dub version, but still two lovers who were unrepentantly evil. (In fact, there's some debate over which was worse among fans; Barbara seemed loyal to him, while he was willing to leave her to die at the end to save his own hide, but on the other hand, he was the ''only'' one she was loyal to, and was willing to betray anyone else to get what she wanted, [[FemmeFatale using seduction and her beauty to do so.]]
* In ''Manga/{{Kekkaishi}}'', this is implied to be the relationship between [[WhiteHairBlackHeart Byaku]] and [[{{Kitsune}} the Princess]], given the fact that not only do the two of them seem to genuinely care about each other, but they seem to ''only'' care about themselves and each other.
[[/folder]]

[[folder:Comic Books]]
* While not married to each other, ComicBook/DoctorStrange villains Dormammu and his sister Umar, both major mystic threats join forces (their mystic power is shared between them) to take ultimate power in a Defenders miniseries. Dormammu spends most of the alliance seeking Umar's approval and Umar finds ways to torment Dormammu. All in all they bicker like a married couple.
* The U-Foes, a MarvelUniverse EvilCounterpart to the ''Comicbook/FantasticFour'' (though oddly not Fantastic Four enemies), naturally also included an evil version of the Richards couple: Vector and Vapor.
* Again in the Marvel Universe, the Absorbing Man and Titania were married. Absorbing Man left her because Titania couldn't let go of her fixation with [[SheHulk She-Hulk]].
* ComicBook/FantasticFour villains the Mole Man and Kala (both rulers of subterranean realms, incidentally) have had a relationship that has been rocky and tumulous. 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.
* Even earlier, TheDCU has the Sportsmaster and the Huntress/Tigress, two [[TheGoldenAgeOfComicBooks Golden Age]] villains revealed to have married when they returned in the 1960s.
** They had a daughter, Artemis, who [[LegacyCharacter became the new Tigress]] and then hooked up with another villain, [[AnIcePerson Icicle]]. Last we heard of them they had a daughter of their own.
* ''Franchise/{{Batman}}'':
** Harley Quinn puts quite a lot of effort into persuading TheJoker to enter into this joyous state, but has only gone so far as MadLove, probably to the benefit of all concerned. She does have a semi-regular relationship with Poison Ivy, whenever Mr J throws her out/tries to kill her or one of them is captured, but it never lasts long due to Harley's obsession with the Joker and/or Ivy's absolute misanthropy.
** ''ComicBook/DeathOfTheFamily'': [[spoiler:Poison Ivy and Clayface]] are now husband and wife. This may seem odd, but it makes sense when one considers that she's [[spoiler: a plant lady]] and he's [[spoiler: a pile of clay (which is a part of the earth), and plants and earth go together just fine!]] [[spoiler: it was a ploy for Ivy, to use Clayface as bait for some plan]]
* 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]].
* In ''CaptainAmerica'', the RedSkull's daughter Sin and her lover Crossbones (one of the Skull's henchmen).
* In the ''Yank Wilson'' story in the first issue of ''Next Issue Special'', Rajiv Bahdgi and his wife Berlin Holiday are... special. Bahdgi's villainous activities have become wild, unfocused, and more destructive than ever since his marriage. When Yank Wilson and his team are sent to apprehend him, we discover why: his overbearing wife has been driving him mad and he wants to be captured just so he can get away. Unfortunately for him, due to the heinous nature of his actions, the government has a special arrangement for him in Leavenworth: he and his wife will be sharing a cell. Cue BigNo.
* In the Crime Syndicate, the MirrorUniverse version of the JusticeLeagueOfAmerica, Superwoman (evil WonderWoman) is married to Ultraman (evil Franchise/{{Superman}}). But she's contemptuous of her husband, and her illicit affair with Owlman (evil Franchise/{{Batman}}) is closer to the trope.
* In the ''[[ArchiesSonicTheHedgehog Sonic The Hedgehog]]'' comics, there's Scourge and Fiona Fox. Fiona pulled a FaceHeelTurn to be with him, and when Scourge took over [[BizarroUniverse Anti-Mobius]] and made himself king, he made her his queen. They seem to actually care about each other, as several times they've both come to each other's aid when it would have been easier to abandon each other.
** There's also the Iron Queen and King, who [[InterspeciesRomance thank]][[{{Squick}} fully]] were just a marriage of political convenience. Though, the Queen did have a thing on the side with Snively, and each seemed to be using each other to advance their positions in Eggman's empire.
* During Stilt-Man's funeral, it's revealed that he and Princess Python from the Circus of Crime had been married.
* In Lois McMaster Bujold's novel ''Mirror Dance'', House Bharaputra is run by a married couple, Baron and Baronne Bharaputra, who appear devoted to each other. [[spoiler/Although in the Baronne's case, it's possible that she's just looking for the extended life in a cloned body that he offers.]]
[[/folder]]

[[folder:Fan Works]]
* Beyond Birthday and Light Yagami in ''FanFic/ThatEpicPlan'':
-->''"In the past few weeks, they'd managed to convince everyone that they were in fact a loving couple rather than two psychopaths hooking up for kicks. Although Light wasn't too sure about L, the detective still seemed suspicious and watched their every move. Although Beyond kept insisting L was just a peeper."''
* 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.
* Dark!Harry and Voldemort in ''[[FanFic/TheDarknessSeries Harry Potter and the Descent into Darkness]]''. After Dark!Harry [[spoiler: helps Voldemort get his body back]] they instantly take a liking to each other.
* Voldemort and Bellatrix Lestrange in ''AVeryPotterMusical''.
** You could also say in a HoYay sense for Voldemort and Quirrell, especially since later in the play [[spoiler: after Quirrell is sent to Azkaban Voldemort's idea of getting off with Bellatrix is to be behind someone's head and hang out. At the end of the play, he and Quirrel are reunited after Voldemort is reduced to just a bodyless soul again needing a host.]]
* [[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...
-->'''[[AuthorAvatar The Author]]''': Then by the power invested in me by myself, I now pronounce you husband and wife. You may kiss the bride, though I would prefer if you didn't.
* It's not unknown for the Grand Highblood and the Condesce of ''Webcomic/{{Homestuck}}'' to be portrayed this way. ''FanFic/{{Hivefled}}'' uses DeliberateValuesDissonance to crank up the villainy; [[spoiler:they're moirails, and so by the standards of their society are supposed to be PlatonicLifePartners who prevent each other from becoming violent. Not only do they actually make each other much worse, they had children, with the intention of torturing and sacrificing them later.]]
* The Blog/AskAPony blogs ''[[http://discorderlyconduct.tumblr.com/ Discorderly Conduct]]'' and ''[[http://cupidite.tumblr.com/ Cupidite]]'', in their frequent crossovers, portray [[GodOfEvil Discord]] and [[EvilMatriarch Queen Chrysalis]] as having had a relationship long ago. [[http://cupidite.tumblr.com/post/40034251127/neverending-story It... didn't end well]], and is strongly implied to be the StartOfDarkness for both of them.
* Arzt and Nie, witch assassins of ''FanFic/ResonanceDays'', are a [[MakingLoveInAllTheWrongPlaces very, very]] intimate couple, who often talk about how [[DeadToBeginWith their arrival in the afterlife]] is proof that [[PowerOfLove love conquers all]]. Most other characters find them saccharine or creepy (and the [[TwinCest uncanny resemblance]] doesn't help). To a lesser extent, the Madam, [[TheDon a brutal crimelord]], and Margot, her BattleButler, have a very close relationship and enjoy nuzzling when not finding inventive ways to torture people who can't die.
* In the ''Manga/{{Naruto}}'' and ''Manga/SoulEater'' {{Crossover}} fic [[https://m.fanfiction.net/s/9883704/1/He-ll-Never-Be-My-Son He'll Never Be My Son]], Orochimaru and Medusa seem very happy together, as romantic partners and {{Evilutionary Biologist}}s helping each other out.
* In the final story of the ''FanFic/MyHostageNotYours'' series, Zim and Gaz -- who transition from {{Anti Hero}}es to full {{Villain Protagonist}}s -- get married a while after taking over North America, and end up honeymooning in Europe after that's conquered as well.
* In ''FanFic/ACharmedLife'' Ryuk and Light shack up together in the Shinigami realm.
[[/folder]]

[[folder:Film -- Animation]]
* [[BigBad Scar]] and [[DragonAscendant Zira]] from ''Disney/TheLionKingIISimbasPride'', even if this relationship is off-screen.
* In ''WesternAnimation/SouthParkBiggerLongerAndUncut,'' {{Satan}} is in a gay relationship with 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 [[TheyKilledKenny Kenny]], Satan finally snaps and kills Saddam.
[[/folder]]

[[folder:Film -- Live Action]]
* Chucky and Tiffany from the ''Film/ChildsPlay'' movies are vicious murderers, but love each other... most of the time.
* In ''[[AustinPowers Austin Powers: The Spy Who Shagged Me]]'', Dr. Evil and Frau Farbissina have a fling, leading to TheReveal that [[spoiler:Scott Evil is their love child]], thanks to some fun with a [[strike:{{Stable|TimeLoop}} ]][[TimeyWimeyBall Time Loop]].
** [[TimeTravelTenseTrouble Before that/after that]], Frau Farbissina gets involved with a female professional-golfer-assassin.
* Sol and Viper, the fun-loving cannibal couple in ''{{Doomsday}}''.
* ''Film/TheMummyReturns'' had Imhotep reunite with a reincarnated Anck Su Namun in an unhealthily [[TheUndead undead]] version of ReincarnationRomance. By the movie's climax he's clinging for dear un-life on the lip of a gaping hole to the ancient Egyptian underworld as the CollapsingLair falls around them and the hero couple. He extends his hands to her for help, and she... [[VillainExitStageLeft leaves.]] Imhotep turns to the O'Connell's (where Evie ''did'' help Rick up) and gives them a heartbreaking smile before [[FaceDeathWithDignity letting go.]] Anck Su Namun got punk killed shortly afterwards.
** Anck-Su-Namun is even ''worse'' in the AnimatedAdaptation. Which is saying something, considering the movie version ''threw venomous snakes at people''. It's implied in the cartoon that Anck-Su-Namun was just in a relationship with Imhotep for chance at achieving power; after he goes through the trouble of resurrecting her, she abandons him the moment she gets her hands on the ArtifactOfDoom [[MacGuffin of the week]]. When they encounter each other again in the series finale, Imhotep is apparently over her, as he leaves her to rot in the Underworld in an AndIMustScream state.
* In the sequel to ''Film/TheCrow'', ''TheCrowWickedPrayer'', Luc Crash and Lola Byrne ''are'' this trope, and are, by all indications, genuinely in love. Then they go through with their [[DealWithTheDevil Unholy Wedding Ceremony]], and Luc gets [[DemonicPossession possessed]] by {{Satan}}...
* The Mayflowers, the {{Card Carrying Villain}}s of the deliciously {{camp}}y ''HudsonHawk'', are ''passionately'' in love with one another in a way that makes them ''more'' villainous and creepy.
** The only time Darwin loses his PsychoticSmirk is when [[spoiler:Minerva is horribly killed by a splash of molten lead]].
* Magneto and Mystique of ''{{Film/X-Men}}''. [[spoiler:However, it is thoroughly broken by ''Film/XMenDaysOfFuturePast'', where they try to kill one another.]]
* [[IncestIsRelative Riff-Raff and Magenta]] from ''Main/TheRockyHorrorPictureShow''.
* Cosmo and Nation McKinley from ''ShockTreatment''.
* In ''Film/FoxyBrown'', the main villain is Katherine Wall, who runs a combined call girl and drug empire. Steve Elias is TheDragon of the organization, but also her lover. Katherine seems quite passionate about him, while Steve seems to have a more pragmatic attitude and keeps flirting with the call girls.
[[/folder]]

[[folder:Literature]]
* Bibok and Calosta in Creator/EstherFriesner's ''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.]]
* In one of the ''ConanTheBarbarian'' stories, titled ''[[http://en.wikisource.org/wiki/The_People_of_the_Black_Circle The People of the Black Circle]]", a villainous sorcerer was [[LadyMacbeth convinced by his lover]] that he should betray his four masters and TakeOverTheWorld on his own. [[spoiler: He was actually able to use ThePowerOfLove to hold all four of them off for a while -- until they realize what's happening, and target HER instead. He gets the last laugh as he [[AlmostDeadGuy live just long enough]] to give Conan information on how to kill them]].
* Odiana and Aldrick in ''Literature/CodexAlera.'' One is an insane water witch, the other is a brutal mercenary. They are also absolutely devoted to each other and every scene of them being together is filled with such tenderness, love, and overt passion for each other that you could easily forget the horrible violence they are perfectly willing to inflict on anyone else.
* In ''Literature/HarryPotter,''
** Lucius Malfoy is a bigoted terrorist who uses his money and power to manipulate others, while his wife Narcissa is a just-as-bigoted snob; yet as the series goes on it becomes apparent that these two's love for each other (and their son Draco) is their strongest and most (well, only) redeeming quality; as Voldemort begins to show just how little he regards any of them, their love for each other over him results in the family's practical HeelFaceTurn.
** Vernon and Petunia. They're selfish and abusive to Harry, yet they seem quite devoted to each other.
** This is exactly what goes on between Voldemort and Bellatrix Lestrange...in the latter's twisted and hopeless dreams.
* ''Literature/DangerousLiaisons'' has as its protagonists the amoral and sociopathic duo of Valmont and Merteuil.
* Poppy Z. Brite's novel ''Exquisite Corpse'' has a gay version of this trope. Andrew Compton and Jay Byrne are necrophiliac serial killers who scheme to murder and eat the secondary protagonist.
* Caine and Diana from ''Literature/{{Gone}}'', by Michael Grant. He's a megalomaniac, power-hungry sociopath. She's a deceptive, selfish, manipulative girl who has betrayed everyone at some point. And yet they're in love, prompting him to [[spoiler:make a temporary HeelFaceTurn, help the heroes, and try to kill his former lieutenant, who had just given her a nearly fatal injury, all for a chance to save her life.]] By ''Plague'', though, [[spoiler:it's debatable whether they love each other, or ever did. [[JerkAss Caine lies to Diana and uses her for sex,]] and [[ManipulativeBastard she leaves his side the second she realizes she can't control him.]] There are, however, those who think their relationship is beautiful, so we'll just leave it at a "maybe".]]
** In ''Light'' it seems to be a definite "yes". [[spoiler: Although admittedly, with a [[RedemptionEqualsDeath very]] [[DyingDeclarationOfLove bitter]] [[HeroicSacrifice sweet]] [[TearJerker note...]] ]]
* Norman and Sandra Arminger from the ''Literature/{{Emberverse}}''. He is ruthless, imaginative, and a powerful warrior; she is cool, brilliant and manipulative. Together they form and control the Portland Protective Association, a medieval recreation/protection racket that seizes control of a huge chunk of the Pacific Northwest after the Change destroys most modern technology.
** Stirling likes this trope: his Nantucket trilogy features the appalling partnership of deranged sadist Alice Hong and her husband William Walker, a genocidal warlord.
* ''Literature/TheDresdenFiles'':
** Esteban and Esmeralda Batiste, nicknamed "The Eebs," who are a husband/wife assassin team for the [[OurVampiresAreDifferent Red Court]]. Susan thinks that their relationship is romantic in an incredibly warped and psychotic way.
-->'''Martin''': They have complementary insanities. Don't justify it with anything more than that.
** The Red Court itself includes Duchess Arianna, an ancient [[MayIncaTec Mayan]] vampire who turned and married the Spanish Duke Paolo Ortega in revenge for what he and his men had helped do to her people.
** Which is nothing compared to the [[TheBlackDeath lovely activities]] [[{{Chessmaster}} Nicodemus]] [[ManipulativeBastard Archleone]] and his wife Tessa come up with.
*** Arguably, this trope ''could'' apply, at least loosely, to Nicodemus and Deirdre, daughter of Nicodemus and Tessa. Yes, [[ParentalIncest that means what it sounds like.]]
* Black-magic users Isaac and Selena Izzard in Creator/JohnBellairs' ''TheHouseWithAClockInItsWalls'', although they're both already dead by the time the story actually starts.
* ''[[GentlemanBastard Red Seas Under Red Skies]]'' has Requin and Selendri. He's the vicious head of a casino where anyone suspected of cheating is put to death; she's his TwoFaced top enforcer. They are both absolutely devoted to one another, to the point where Requin hideously burned his hands trying to scrape off the contact poison that led to Selendri's current condition, then did something unnameable to the man who took out the hit.
* Literature/InDeath series: This has happened a couple of times, like in ''Salvation in Death'' and ''New York to Dallas''. However, in those cases, one of the couple is genuinely in love and the other has nothing but contempt for the other. The contemptuous one will murder the other one, thereby crossing the MoralEventHorizon...if s/he has not already done so!
* Literature/SisterhoodSeries by Creator/FernMichaels: A number of stories has this going on between the bad guys, like in ''Lethal Justice'', ''Vanishing Act'', and ''Deadly Deals''. However, the "love" between such couples is apparently not genuine, and they will inevitably turn on each other once the Vigilantes and {{Karma}} start closing in on them!
* It was apparent from the start that Billy-Ray Sanguine from ''Literature/SkulduggeryPleasant'' has a twisted affection for Tanith Low but it was only when [[spoiler: Tanith got a Remnant permanently bonded to her soul]] that she started reciprocating those feelings. What makes it even worse is that Tanith is not in full control of what she's doing and so there's some very rape-y overtones on top of that. {{Squick}} indeed.
* In ''Literature/ThoseThatWake'''s sequel, Arielle and Roarke are close, and implied to be romantically linked.
* In Lois McMaster Bujold's novel, ''Mirror Dance'', Baron and Baronne Bharaputra, the evil heads of House Bharaputra, appear devoted to each other.
[[/folder]]

[[folder:Live Action TV]]
* ''Series/TheAddamsFamily'' is more AffablyEvil than outright villainous, but Moricia and Gomez's relationship could technically qualify as this. They are a very loving couple, and [[VillainProtagonist their show]] is one of the few sitcom-style series on TV without marital strife as a running gag.
* [[Series/BuffyTheVampireSlayer The Buffy]][[Series/{{Angel}} verse]]:
** Angelus and Darla. Once Darla teamed up with Angelus, the duo started traveling the world, often staying wherever a genocidal civil war was currently going on.
** Likewise, Spike and Drusilla, who seemed to be genuinely in love, albeit still quite psychotic. Sad it didn't last through all of the seasons. Spike's later relationship with Harmony counts as this as well, though it rather notably doesn't really work quite so well and doesn't last nearly so long, for [[ReplacementGoldfish more]] than one [[YouHaveOutlivedYourUsefulness reason]].
** Lindsey and Eve.
** Harmony with Hamilton.
** Vampire Willow with Vampire Xander.
* ''Series/{{Charmed}}'': Quite literally, if someone wants to remain aligned with Evil in marriage. It must be performed with a Dark Priest, at night, in a cemetery.
* ''Series/ChinesePaladin'': Used as a means of demonstrating ThePowerOfLove, when the heroes find a snake and fox-demon couple preying on travelers. The snake-demon [[HeroicSacrifice sacrifices his physical form]] to save his wife, who then pledges to devote herself solely to preserving his soul. [[spoiler: Unfortunately, the hero doesn't know about that, and kills her too.]]
* ''Series/CriminalMinds'': Anita and Roger Roycewood, the couple of [[spoiler: child abductors and murderers]].
* ''Series/{{Dexter}}'': A couple show up as Victims of the Week, telling each other that they love each other even while Dexter is about to kill them for murdering several innocent immigrants.
* ''Series/HerculesTheLegendaryJourneys'' and ''Series/XenaWarriorPrincess'': Over the course of both shows, Ares has been romantically involved with both Callisto and Hope, even impregnating the latter.
* ''Series/HouseOfCardsUK'': [[TheUsurper Francis Urquhart]] seems to have a genuinely loving and mutual relationship with his wife, to the point where she will allow and even suggest that he have affairs in order to [[UnwittingPawn gain someones trust.]] She knows all of his devious acts [[spoiler:(including the murders)]] and they conspire and live together happily.
* Same applies to ''Series/HouseOfCardsUS''.
* ''LoisAndClark'': Had a rich SickeninglySweethearts couple who kept their marriage alive by brewing evil plans together.
* ''TheMiddleman'': Vlad and Lizzie the vampire couple.
* ''Series/TheNewStatesman'': Even though he's the protagonist, Alan B'Stard and his wife Sarah are both amoral and power-hungry enough to qualify for this trope. (They take the idea of a "love-hate" relationship to whole new levels...)
* ''Series/{{Nikita}}'': It's eventually revealed that Amanda is in a secret alliance/relationship with Ari Tasarov; together, they plot against both the protagonists and [[TheStarscream their respective superiors]], in order to gain more control and power for themselves. Even after their master plan fails [[spoiler: and they're forced to go on the run]], it's shown that they actually do truly care about each other. One could even argue that their relationship itself is an EvilCounterpart to the one between Nikita and Michael.
* ''Franchise/PowerRangers'':
** In ''Series/MightyMorphinPowerRangers'', Lord Zedd and Rita Repulsa actually went as far as subverting the inevitable failure of the LovePotion - and eventually getting married. Later it's revealed that Zedd loves Rita for real, when he is exposed to an antidote against the love potion. The behind-the-scenes reason for this Unholy Matrimony is that the MoralGuardians thought Zedd, acting as an evil overlord, was too scary for kids during his early run. Therefore the producers toned him down by making him part of a bickering married couple.
** This is why SpacePirate Divatox wanted to release Maligore in the ''Series/PowerRangersTurbo'' movie. She started having second thoughts after getting a good look at him, seeing that he is a berserk fire demon.
** In ''Series/PowerRangersZeo'' there were two cases of villains who had been married before making their first appearance (in a way, considering that both couples were robots). King Mondo had Queen Machina as his royal consort, and likely had for a long time. Also, Mondo's firstborn (first-built?) son Prince Gasket had eloped with Princess Archerina, the daughter of Mondo's rival, at some point in the past, and the two later returned when Mondo was believed to be dead.
* ''Series/{{Revolution}}'': As of [[Recap/RevolutionS1E8TiesThatBind episode 8]], Major Tom Neville and his wife Julia are revealed to have this going on between them. Their love seems to be quite genuine, considering that they went to great lengths to save their son's life, and that Julia is urging Tom to kill off Monroe and take his place as head of the Monroe Republic. [[Recap/RevolutionS1E10NobodysFaultButMine Episode 10]] shows that Tom would surrender before he sacrifices Julia. [[Recap/RevolutionS1E13TheSongRemainsTheSame Episode 13]] has Tom fail a mission for Monroe, and so he personally hurries to Julia and has her pack up and flee the Monroe Republic with him.
* ''SpartacusBloodAndSand'':
** Batiatus and Lucretia have a great and loving relationship, but are the BigBad for the entire first season. Notably a lot of their scheming, both in "Blood and Sand" and the prequel "Gods of the Arena" is done for love of the other, and they seem to bring out the worst in each other.
** While Glaber and Ilithyia have a rockier relationship, they are matched in ambition and scheming skills. By the end of ''Vengeance'', in the episode "Monster" they reunite for evil and declare they are both monsters. To stress the point they proceed to have sex covered in the blood [[spoiler:of Seppia, whose corpse is still floating in the pool next to them.]]
* ''TrueBlood'': Russell Edgington and Steve Newlin. [[spoiler: Slow dancing to Katy Perry in a frat-house full of bodies they've fed and murdered, flirting while glamoring Jason into showing where the fairies and his sister are hidden, Russell kidnapping a small werewolf girl so Steve can have his "first pet"...]] It's cute, on a sociopathic level.
* ''TheVampireDiaries'': InvertedTrope: Damon loves Katherine but she's more interested in his [[FriendlyNeighbourhoodVampire little brother]].
[[/folder]]

[[folder:Music]]
* The AxCrazy couple in "A Little Piece of Heaven" by Music/AvengedSevenfold.
* Precisely 50% of the songs on [[FilkSong Seanan McGuire]] album [[http://www.cdbaby.com/cd/seananmcguire3 Red Roses and Dead Things]] are about this trope, with [[SlidingScaleOfSillinessVersusSeriousness varying degrees of creepiness]].
* "[[http://www.youtube.com/watch?v=CHAVRAD_c-Y Lucifer]]" by Music/{{Blutengel}}.
* A lot of Ordo Rosarius Equilbiro's work fits this trope. Especially "[[http://www.youtube.com/watch?v=yOCxtDHk89M&feature=related Do Lust and Murder Make Me a Man?]]" and "[[http://www.youtube.com/watch?v=N8wWcr28_Rk Let the Words of My Murder Be the Last Words You Hear]]."
* "Killers in Love" by TubRing.
[[/folder]]

[[folder: Mythology and Religion]]
* OlderThanFeudalism with ClassicalMythology:
** [[HeroKiller Typhon]] and [[MotherOfAThousandYoung Echidna]]. She's a beautiful woman with the lower body of a snake, and a fondness for eating travellers. He's a giant with one hundred dragon heads, and a tendency towards deicide. Together they sired the {{Hellhound}}s [[MultipleHeadCase Orthrus and Cerberus]], the [[MixAndMatchCritters Chimera]], the NighInvulnerable [[PantheraAwesome Nemean Lion]], the [[RiddleMeThis Sphinx]], the [[GiantFlyer massive eagle]] [[ToServeMan that ate Prometheus' liver]] and the [[HealingFactor nearly]] [[HydraProblem unkillable]] Hydra. It becomes even better if you realise that among the Greek pantheon they're probably the two deities/monsters [[HappilyMarried who are the most faithful to one another]]; there are no reports of either sleeping around (admittedly, when you look like that...), in sharp contrast with [[JerkassGods Zeus]], who to say the least, ReallyGetsAround. Truly a match made in [[{{Hell}} Tartarus]] (who is coincidentally, their father).
** Neither Hades nor Persephone were really evil ([[EverybodyHatesHades despite popular belief]]), but both were feared by the ancient Greeks and were [[DarkIsNotEvil generally dark beings]] (yes, [[NatureSpirit Persephone]] too, in her role as Queen of the Underworld). Their marriage may have been based on [[AbductionIsLove kidnapping]] at first, but if nothing else Hades was far more faithful than the average god.
[[/folder]]

[[folder:Professional Wrestling]]
* {{Lita}} and {{Edge}} are an iconic example.
* DolphZiggler and [[ChickBusters AJ Lee]] are an evil power couple, but seem so blissfully happy together that it's hard not to root for them.
[[/folder]]

[[folder:Radio]]
* In BigFinishDoctorWho audio drama [[BigFinishDoctorWho064TheNextLife The Next Life]], [[spoiler:Zagreus and Daqar Keep become this at the end.]]
[[/folder]]

[[folder:Tabletop Games]]
* From ''TabletopGame/{{Warhammer}}'', the vampire couple Vlad and Isabella von Carstein. After turning Isabella into a vampire he raised a giant army of the undead and they tried to conquer TheEmpire. As you do. When Vlad was slain Isabella committed suicide.
** Vlad took Isabella as his bride to seize control of Sylvania. He fell in love with her afterward, while she was still human, and did everything he could to ''avoid'' turning her into a vampire. Then a plague hit Sylvania, the doctors couldn't do anything for Isabella when she caught it, and Vlad, out of options, gave her an EmergencyTransformation. She took it amazingly well.
** In gameplay, if you have both on the table and one of them is killed then the other[[BerserkButton goes completely insane]], picking up Hatred of the enemy army and Frenzy. Translation: the bereaved spouse charges directly at the enemy lines and tries to rip apart the bastards that killed their love with claws and fangs.
* From ''TabletopGame/DungeonsAndDragons'', Count Strahd Von Zarovitch believes that [[spoiler:every hundred years his old love interest from before becoming a vampire is reborn. Naturally, he tries to marry her every single time. (He will never succeed, however; a Domain of Ravenloft is an IronicHell for its ruler, and for Strahd, this is the exact reason why.)]]
** Another famous example of this from Dungeons & Dragons (which ended badly) was the relationship between Mammon, the ruler of the third layer of Baator, and Princess Glasya, the daughter of Asmodeus. Glasya was his lover and consort, but after the failed mass coup called the Reckoning, Mammon proved to be a groveling coward before Asmodeus. As part of his punishment, Asmodeus forced him and Glasya to annul their marriage. Glasya has since become [[TookALevelInBadass far more powerful]] and become ruler of the sixth layer, and her attitude towards him now is unknown; some believe that they have secretly renewed their relationship (despite the fact that Mammon has a new consort) while others believe she despises him now for failing to defend their love.
* From ''TabletopGame/{{Deadlands}}'' fluff, we have Miles and Mina Devlin, ruthless railroad barons, dark sorcerers, devoted spouses and loving parents. [[spoiler:After Miles' assassination, things go downhill.]]
[[/folder]]

[[folder:Theater]]
* Mr. and Mrs. Mao Zedong are largely portrayed as a loving and romantic, if [[LovingForce occasionally]] [[CulturePolice disturbing]] couple. The song ''The Chairman Dances'' is dedicated to this trope.
* ''Theatre/SweeneyToddTheDemonBarberOfFleetStreet'': Sweeney Todd and Mrs. Lovett has shades of this, even though they're not married and she's the only one who wants a RelationshipUpgrade.
* Monsieur and Madame Thénardier in ''Theatre/LesMiserables''. Though how deep the love goes is questionable. "I used to dream that I would meet a prince- but God Almighty have ya seen what's happened since?!"
* In ''Theatre/TwelfthNight'', Toby and Maria spend a lot of time together preparing [[BatmanGambit Batman Gambits]] in order to make fools of others, [[spoiler:and sure enough, at the end of the play we find out that they've eloped]].
[[/folder]]

[[folder:Video Games]]
* To confront and expose the BigBad in ''VideoGame/BaldursGate'', the characters first have to get an invitation to his inauguration ceromony in the Duke's Palace. They get one from the two assassins Slyth and Krystin who hang out in the Undercellar brothel before they get to kill the remaining dukes. These two seem quite crazy and nauseatingly in love, and manage to put up quite a fight when you encounter them for the first time.
** In the sequel you can cause this. There is two characters talking about how their familes are driving them apart since they're a bad influence on each other. One of your options is to be a LoveFreak and tell them that they should run off together. They thank you and tell you everything they do shall be in your name. Later you overhear a conversation about those two. Turns out they were an OutlawCouple and are now robbing people in your name.
* Alice and Decus of ''VideoGame/TalesOfSymphoniaDawnOfTheNewWorld'', with the "one playing the other" thing (gender-flipped). When Decus becomes a LoveMartyr, that changes everything...
* 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 SamuraiWarriors starting from the second game. (In the first, she struggled between killing him and killing ''for'' him.)
* ''VideoGame/{{Overlord}}'' gives you a choice in Mistresses, though there's always one that's actually relatively non-evil and arguably the [[OnlySaneMan Only Sane Person]] in this CrapsackWorld. First game featured the prim and proper Rose and the greedy and slutty Velvet. The second game (which confirms [[spoiler:Rose]] as the canon choice) offers VictoriousChildhoodFriend Kelda, GoldDigger Juno and [[spoiler:FallenHero Dark Fay]].
* Subverted in ''VideoGame/WorldOfWarcraft'', where the quarreling demon couple in Acratraz lets the heroes attack them one at the time while the other provides 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:FamousLastWords following her allegedly final defeat]]:
--->[[spoiler:'''Whitemane''': 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|Button}} Aspect of Magic. And then death, too, in The Nexus.
* Lady and Killer from ''ShadowHearts: From the New World''. Though whether the latter was actually in love or merely {{Mind Control}}led is debatable.
* In ''VideoGame/KnightsOfTheOldRepublic'', [[spoiler:Bastila]] suggests this possibility to a male PlayerCharacter near the end. [[spoiler:You can take her up on it]].
** If they had actually ''finished'' the second game, this would have been possible with whichever love interest you chose on the dark side path.
* A possibility with Blackguard Aribeth and the player in the end of ''NeverwinterNights Hordes of the Underdark''; or if you pick the evil path in ''NeverwinterNights2 Mask of the Betrayer'' the player and Gann/Safiya (depending on gender).
** Before it was cut, an evil female player and Bishop in ''NeverwinterNights2.''
** Certain mods do have examples, including Vico and the player in ''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.]]
** Before that, it is discussed at the end of Chapter 4, [[spoiler:when, after [=LeChuck=] breaks free from prison and saves Guybrush and Elaine after the cure of the [[HatePlague Pox of LeChuck]], he tells our hero that "it was the only way to win Elaine's hand in unholy matrimony"... getting him confused and allowing [=LeChuck=] to make [[InTheBack a clever, fatal ambush on him]].]]
* ''VideoGame/{{Catherine}}'': in one of the MultipleEndings, [[spoiler:[[LikeABadassOutOfHell 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, helps to earn them RedemptionEqualsLife in one of the game's endings. Their feelings for each other are both very mutual and very genuine.
* While not exactly the main vilains, William and Annette Birkin in ''VideoGame/ResidentEvil2'' seem to be a happily married couple of scientists. [[MadScientist Mad Scientists]]!
* [[TheBrute Black Scorpion]] and [[CombatSadomasochist Silver Mantis]] seem to have this sort of relationship in ''Videogame/CityOfHeroes''.
* ''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.
* Being made by BioWare - and a direct sequel to the ''KnightsOfTheOldRepublic'' games mentioned above - it comes as no surprise that the MMO ''StarWarsTheOldRepublic'' has this. The main example is 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 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...
** It's also possible for a 'Darkside' player character to start a relationship like this, with an equally-evil companion. Perhaps the most poignant of these options is the Male Sith Warrior, who can [[spoiler: corrupt the Jedi Padawan, Jaesa Wilsaam to the Dark Side, and take her as your apprentice - and later, lover. She even admits that, to her own disappointment, she can't live up to the true Sith Ideal, since that includes seeking to [[KlingonPromotion betray and murder your Master]] when you get the chance - and she can't do that since she's fallen for you.]] Awwww...
** On the other hand, if you play your cards right, it's also quite possible for a Darkside player to start and maintain a relationship with a 'Lightside' companion, and acting genuinely carring towards him/her even as you slaughter innocents and inflict pain and misery left and right. Which creates a whole 'nother spin on this trope...
* In Mileena's non-cannon ending of ''VideoGame/MortalKombat2'', she is a "secret partner" with Baraka, they both [[TheStarscream kill Shao Kahn]] and takes over the Outland, ruling it as king and queen.
* ''VideoGame/TheElderScrollsVSkyrim'' has Astrid and Arnbjorn of the Dark Brotherhood, two assassins who happen to be married.
* ''DynastyWarriors'' from 5 onwards has an example in the couple of Cao Pi and Zhenji. She is a [[{{Sadist}} sadistic]] LadyMacbeth, he is the [[AmbitionIsEvil ambitious]], [[AnIcePerson cold-as-ice]] [[OverlordJr successor to the Throne of Wei]]. Together, they [[AuthorityEqualsAsskicking 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]].
** Interestingly, this is quite a divergence from the [[RomanceOfTheThreeKingdoms source material]], in which Cao Pi amused himself with Zhenji for a while - after killing her first husband and basically 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''.
[[/folder]]

[[folder:Visual Novels]]
* In ''UminekoNoNakuKoroNi'', 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''.
** [[MonsterClown Li'l Ronnie/Ran-Ru]] and her Servant [[ActuallyNotAVampire Lancer]] in ''VideoGame/FateExtra''.
* The {{Villain Protagonist}}s Fuminori Sakisaka and Saya from ''VisualNovel/SayaNoUta''.

[[/folder]]

[[folder:Web Comics]]
* In the webcomic ''Webcomic/CheshireCrossing'' - which is essentially a MassiveMultiplayerCrossover among ''Film/TheWizardOfOz'', ''Disney/AliceInWonderland'', ''Disney/PeterPan'' and ''Film/MaryPoppins'', with a couple of historical characters thrown in for good measure - The Wicked Witch of the West finds her way to Neverland, and after meeting up with Captain James Hook, the two start a rather [[http://www.cheshirecrossing.net/page.php?issue=4&pagenum=0 *intimate* partnership]]. This also effectively turns her into a [[NinjaPirateZombieRobot witch-pirate, or maybe pirate-witch]], which is awesome. Pirate.
* In ''Webcomic/TheOrderOfTheStick'', [[EvilTwin Nale]]'s girlfriend, Sabine, is a succubus - truly a match made in hell (or the Abyss if you want to get technical). Their love is maintained [[http://www.giantitp.com/comics/oots0349.html through black magic and human sacrifice]]. And [[PowerPerversionPotential shapeshifting]]. While often played for laughs, there actually ''does'' seem to be a more serious side to their relationship which one can sense when Sabine talks to Vaarsuvius.
** Later strips would emphasize just how much Sabine cares for Nale; [[spoiler: [[http://www.giantitp.com/comics/oots0804.html She seems to imply]] she would defy the Archfiends for him]]
** Also, it can even make [[http://www.giantitp.com/comics/oots0489.html a secondary unit of measure]] (in this case, a constant level of evil of 4.8 kilonazis with 0.4 kilonazi deviation):
--> '''Roy''': Who does the green line represent?\\
'''Deva''': A hypothetical offspring of [[Disney/OneHundredAndOneDalmatians Cruella de Vil]] and [[Literature/TheLordOfTheRings Sauron]].
* During a {{Flashback}} sequence in ''GeneralProtectionFault'', it's revealed that Trudy - [[TheChessmaster chessmaster]] and {{Puppetmaster}} extraordinaire - had a 'teamup' like this during college, with an equally despicable individual named Trent, who later became her archnemesis when he betrayed her.
-->'''Trudy''': We both had this... ''appreciation'' for the sadistic and morbid. We enjoyed our evil pranks so much that we quickly fell deeply in love with each other. It was ''black magic''.
* Subverted in Episode Five of the webcomic ''{{Demonology 101}}'', when [[spoiler: Isaac, the main villain, and Madeline, his demon 'handler,' genuinely falls in love halfway through the episode. She was supposed to keep him out of trouble, but once she starts sympathizing with him, winds up encouraging him to kill his brother Gabe. (As if he needed more encouragement.) However, when she herself is fatally injured, Isaac willingly barters her cure for a final truce with Gabe and the other protagonists.]]
* ''MinionsAtWork'': [[http://www.minionsatwork.com/2009/01/overlords-148-snake-eyes.html Leading up to it]].
* ''Webcomic/{{Narbonic}}'': [[spoiler:Dave and Helen, eventually.]]
* Axel and Aerith in ''AnsemRetort''. Axel's a homicidal evil Buddhist god and Aerith's a conniving bitch who actively used Axel to get revenge on Cloud. And she admits to having a murderer fetish.
** And then [[http://www.ansemretort.org/ansemretort/index.html?comic=712 Aerith got worse]]...for [[ButtMonkey Riku]], at least.
-->'''Riku''': Well, my skull's caved in and I'm stuck in the ceiling. I think I popped some vertebrae too.\\
'''Aerith''': Well, pop 'em back in! You've got more slings to be shot out of!\\
'''Axel''': God I love you.
* In ''KevinAndKell'', Angelique is accidentally set up with R.L. after someone hacked into the Flea Bay website for a grooming date. R.L. plans on eating Angelique at the end, but becomes enamored with her after hearing Angelique brag about cheating on Kevin during their marriage, and managing to get him to pay her alimony despite initiating the divorce. The two soon marry after Angelique gives R.L. secrets on catching rabbits. Even when R.L. was missing (presumed dead) and Angelique took over Herd Thinners, restructuring it and using it as a stepping stone to conquer the world, he wasn't bitter. He just pointed out what a headache world conquest was. Angelique agreed to just make loads of money instead. And when the two shared a prison cell, they were just happy to be together. The only thing they needed beyond each other to be happy was their kids.
* "Black Hat Guy" and...his...um...[[http://xkcd.com/433/ girlfriend]] in ''Webcomic/{{xkcd}}''.
* Brian and Angelo in ''OurLittleAdventure''.
* Didi and Gogo in ''[[http://vanheist.deviantart.com/art/fine-young-cannibals-87201971 Fine young cannibals]]'' by [=VanHeist=], inspired by ''[[Theatre/SweeneyToddTheDemonBarberOfFleetStreet Sweeney Todd]]''. Aren't they a cute pair?
* Occurs between [[MadScientist Mad Scientists]] Spencer Ecchs and Ada Byon in ''PatchworkChampions''. [[spoiler: She seduces him on the orders of another supervillain to steal his secrets, but when she carries out her mission successfully, the two continue to date, ending with her joining Ecchs's group and marrying him.]]
* In ''Webcomic/SluggyFreelance'', it looked like Crushestro and Monicruel were heading this way, until Chestro, his real wife, arrived. If she's not [[EvilerThanThou eviler than them both]], she's at least more wrathful, and knows how to hit a cheating husband where it hurts -- his criminal conglomerate.
** Nonetheless, Crushestro didn't waver - and, in fact, divorced his wife to stay together with Monicruel. They are adorable together. [[spoiler: Or were, until Hereti-Corp attacked their secret base and hit Monicruel with a DFA. Crushtero survived - barely - and his reaction to seeing her apparently disintegrated]] certainly removed all doubt about HIS feelings, at the very least.
* [[TheChroniclesOfNarnia Jadis the White Witch]] in the MegaCrossover FanWebcomic-verse ''{{Franchise/Buildingverse}}'' is prone to have such relationships. Her ex in the backstory of ''Webcomic/{{Roommates}}'' is the [[Literature/TheErlking Erlkönig]] and she is currently together with [[Film/{{Legend}} Darkness the Prince of Darkness]] in ''Webcomic/GirlsNextDoor'' (her a son from the first relationship doesn't ''need'' enemies: Has two parents from hell and a stepfather he loathes with passion).
* ''Webcomic/GirlGenius'' had a [[http://www.girlgeniusonline.com/comic.php?date=20120224 rather hilarious scene]] when two AxCrazy characters finally found each other. Bangladesh [=DuPree=] suffered instant infatuation with Vole upon hearing a bloodthirsty visionary rant from this [[SuperSoldier walking death machine]]. She even [[DramaticDrop dropped]] Tarvek whom she tried to torment at the time.
* [[KnifeNut Jack Noir]] and [[GodSaveUsFromTheQueen the Black Queen]] from ''Webcomic/{{Homestuck}}'' are a [[MasochismTango weird version of this]]. Specifically, they are considered to be in a kismesissitude, a sexual relationship based around hatred.
[[/folder]]

[[folder:Web Original]]
* Some examples in the ''Literature/WhateleyUniverse'', natch. Some of the Bad Seeds (a clique you can only join if at least one of your parents is a supervillain) go to [[SuperheroSchool Whateley Academy]]. Nephandus has as parents The Troll Bride and Hexmaster. In a slight subversion, they're regarded as the Battling Bickersons of the supervillain world.
* ''Literature/{{Worm}}'' has a very creepy example in Night and Fog, neo-nazi supervillains who [[StepfordSmiler act out the role of a married couple]] with so little feeling that even their teammates find it disturbing.
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[[folder:Western Animation]]
* In the ''WesternAnimation/TransformersAnimated'' episode Society of Ultimate Villainy, a new villan 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.
--> '''Slo-Mo''': I like a man who does it fast.
--> '''Nanosec''': I like a girl who takes it slow.
** 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.
* In an episode of ''WesternAnimation/KimPossible'', 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 seemed to be downright jealous...
* One episode of ''WesternAnimation/CareBears'' 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...
* In ''WesternAnimation/{{Gargoyles}}'', Xanatos and Fox make for an AffablyEvil - or, after their shared HeelFaceTurn, [[MagnificentBastard Affably Magnificent]] - couple. The [[EvilIsCool fans love 'em]].
** 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.)
** [[TheFairFolk Oberon and Titania]], though calling them evil is [[BlueAndOrangeMorality a bit of a stretch]].
* Azula tries to invoke this with Chan, a guy she meets at a party in the [[BeachEpisode Beach]]/VillainEpisode of ''WesternAnimation/AvatarTheLastAirbender'', openly stating that she plans to conquer and rule with him by her side. Since Chan is a JerkJock but not a power-mad despot, he's predictably terrified.
** SequelSeries ''WesternAnimation/TheLegendOfKorra'' gives us a [[EvenEvilHasLovedOnes seemingly very genuine]] and [[EvilVirtues almost sweet]] example with the AffablyEvil EmpoweredBadassNormal Zaheer and the [[StatuesqueStunner towering]], [[ColdSniper aloof]], and [[HavingABlast volatile-in-more-ways-than-one]] DarkActionGirl P'Li. While [[spoiler: Bolin is captured by them]], he hints that [[WildHair long-haired]], [[AffablyEvil incongruously jovial]] [[MagmaMan lavabending]] Ghazan and HandicappedBadass [[MakingASplash water]]-and-[[AnIcePerson ice]] Ming-Hua have an [[CannotSpitItOut unspoken attraction]]. They don't [[spoiler:(and [[KilledOffForReal never do]])]] confirm it, but they share an awkward look with each other.
* 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.
* An example of two villains who are a couple from the beginning is Boris and Natasha of ''WesternAnimation/RockyAndBullwinkle''.
* Another one (which arguably fits the HappilyMarried Trope more than any other example on this list) is the Monarch and Dr. Girlfriend (pictured above) of ''WesternAnimation/TheVentureBrothers'' (they get married at the end of the second season and become an officially licensed supervillain team at the start of the third season).
* Johnny 13 and Kitty from ''WesternAnimation/DannyPhantom''
** Also, though not nearly as blatantly, Skulker and Ember.
** And, "The Ultimate Enemy" reveals that [[EvilChef the Lunch Lady]] and [[FutureBadass the Box Ghost]] have a KidFromTheFuture together.
* King Sidorak and his Viceroy Roodaka in ''Franchise/{{Bionicle}}: Web of Shadows'' (yes, a NoHuggingNoKissing franchise - blame the PromotedToLoveInterest trope). Sidorak does seem to have a fondness for Roodaka (which could be taken as strictly platonic), but he mainly [[WeCanRuleTogether offers her his throne]] as a way to slake her power-lust and keep her out of trouble. She, on the other hand, realizes that under the right circumstances, [[ICanRuleAlone once she's Queen he becomes expendable...]]
** It's left kinda vague in the movie, but other story material later explained there was no romance involved from either side -- Sidorak merely wanted to "marry" Roodaka because then he'd have gotten political influence over her island. Actually, since it's also been revealed that Sidorak's achievements were actually Roodaka's doings, and he only stole the credit from her, it's clear that both were seeing each other as mere tools. It's just that, again, the movie makes it look like he had the hots for her.
* In ''WesternAnimation/ElTigre'' this happens between Puma Loco and Sartana of the Dead. It seems that both of them are faking it at first, but towards the end it is revealed that Puma Loco does holds a torch for Sartana. It gets a little {{Squick}}y as Puma is human while Sartana is a walking skeleton. WordOfGod says that they had a son together, though their relationship was on and off.
* Destro and TheBaroness from ''WesternAnimation/GIJoe''. 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.
* An episode of ''WesternAnimation/PhineasAndFerb'' featured MadScientist Doofenshmirtz dating a woman just as evil as he was. [[http://www.youtube.com/watch?v=iQsmupllGEs 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]].
* [[EvilTwin Anti-Cosmo and Anti-Wanda]] on ''WesternAnimation/TheFairlyOddparents''.
* 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.
* Some [[PeripheryDemographic older fans]] of ''WesternAnimation/WildKratts'' sense a bit of BelligerentSexualTension between [[RichBitch Zack]] [[EvilGenius Varmitech]] and [[TheFashionista Donita]] [[TheCruella 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.
* 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).
* 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.
* [[ManipulativeBastard Darkstar]] and [[DarkActionGirl Charmcaster]] in one episode of ''WesternAnimation/Ben10UltimateAlien''. Of course, Darkstar being [[{{Jerkass}} Darkstar]], he was merely trying to take advantage of her by using her as basically a power source. And of course, since she was the strongest of the two, this ''[[WomanScorned doesn't]] [[KickTheSonOfABitch end well]]'' for him when she finds out the truth...
* ''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]].
* [[spoiler:Fred's real parents]] in ''WesternAnimation/ScoobyDooMysteryIncorporated''.
* In ''WesternAnimation/SouthPark,'' SaddamHussein and {{Satan}}, though most of their in-series appearances are after they break up. See above in "Films--Animated."
* In ''WesternAnimation/EarthwormJim'', [[CatsAreMean Evil the Cat]] gets a girlfriend in Malice the Dog, his DistaffCounterpart. Unfortunately for him, she has to leave for another universe when she gets offered a star role in her own TV show.
* In ''XiaolinShowdown'', it was [[ShipTease highly]] [[UnresolvedSexualTension hinted]] that [[MagnificentBastard Chase Young]] and [[DarkActionGirl Wuya]] were this.
* ''CodenameKidsNextDoor'' had oneshot villain duo Mega-Mom and Destructo-Dad. They're Chad Dickson's parents.
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