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.You know how the story goes, right? The Big Bad meets The Baroness, The Baroness meets the Big Bad, 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 The Power of Love is enough to give even the most hardened group of heroes a serious challenge, and worse yet, 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 Alas, Poor Villain scenario, and maybe even a My God, What Have I Done? Should another villain start messing with the happy couple, it's usually played as a Kick the Dog 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 is genuine but unrequited, expect the one who genuinely loves to sacrifice their life to protect the other, only for the other to disdainfully ignore them as they lie dying, proclaiming that they're no longer useful. Usually, this signals a crossing of the Moral Event Horizon. If both were faking it, expect them to show their true colors at the same time. Hilarity Ensues—and it's never mentioned ever again. The most classic version of this trope occurs when two previously established antagonists suddenly take a new-found 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, Enemy Mine 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 Big Bad Duumvirate. Compare Villainous Friendship, when the two are truly friends with each other, but not in a romantic way. Contrast Minion Shipping (which involves minions instead of actual villains) and Mad Love (which is one-sided). Outlaw Couple is the petty crime version of this. In the case of fiction with 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 Heel–Face Turn or at the very least a "Get out of Jail Free" Card. If the couple in question is heterosexual, expect the man to be the more important half of the couple, possibly making her more of a Dark Mistress. Subtrope of Even Evil Has Loved Ones. Not to be confused with Awful Wedded Life, which describes the marriage itself to be terrible, not the couple in question.
Mr. Freeze: Adam and Evil.
Mr. Freeze: Adam and Evil.
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- 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, Alyssa's a Tykebomb rather than a true villain, and Miyu simply believes in My Master, Right or Wrong.
- Sensui and Itsuki from YuYu Hakusho are a rare homosexual example. Well, sometimes...
- Kunzite and Zoisite in the first Sailor Moon series. Homo or hetero, depending on version.
- In Death Note, there is Light and Misa. Just what the Villain Protagonist needs: A 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 Majin Tantei Nougami Neuro, a psychotic shapeshifting serial killer and his best friend and lover the terrorist.
- In Rurouni Kenshin Shishio Makoto and Yumi have a bit of a subversion on this. Yumi legitimately loves Shishio... 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 Neutral Female. He then 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 take over hell together. Along with Shishio's devoted Battle Butler; he lights up at the thought of going into Hell if it means serving his master.
- In Overman King Gainer, Siberian Railroad executive Yassaba Jin and his dragon, Adette, are very much in love, and actually make a pretty cute couple. Indeed, Jin's combat-prowess 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 Love at First Sight.
- Khyron/Kvamzin Kravshera and Azonia/Laplamiz from Super Dimension Fortress Macross/Robotech. They weren't married but had HEAPS of Belligerent Sexual Tension, he gave her a Forceful Kiss once, and they ended up Together in Death.
- Claire and Chane from Baccano!. They actually end up quite Happily Married.
- Marriages between the morally questionable appear to be genetic, as Chane's father Huey's one and only true love was a misanthropic serial killer, Monica Campanella.
- A joke ending in the DS game has Claire wind up in a just as happy - and far more depraved - marriage with Ladd Russo.
- Debatably, Isaac and Miria also qualify — though they're more in the Plucky Comic Relief Anti-Hero role than anything else.
- Flame of Recca has Mokuren and Mikoto. They're quite happy until she gets wounded and he decides to just kill her For the Evulz. She probably should have known better.
- Code Geass gives us Emperor Charles vi Britannia and his not-so dead wife Lady Marianne who are very much partners in crime, in love with each other, and evil.
- In 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 Kagerou-Nostalgia Evil Overlord Kiyotaka Kuroda appears to have his wife, Yasha, and his son, as Morality Pets. 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 Morality Pet. Rikimaru would really love to be this with his Gender Bendered Co Dragon and Heterosexual Life Partner Ranmaru.
- Kriem and Jake Martinez in Tiger & Bunny.
- Dio Brando, a century-old vampire and Enrico Pucci, a morally ambiguous catholic priest make up for a very interesting case in JoJo's Bizarre Adventure. Although it's still controversial if they are this or villainous friends, the author himself has lately confirmed Dio to be into both men and women.
- Subverted in Fushigi Yuugi. Soi loves Nakago, but he doesn't seem to reciprocate (although he does use her Deus Sex Machina to heal, and generally treats her pretty nicely for a Big Bad of his caliber). However, Soi gets killed in battle, and Nakago carries her corpse around. Make of that what you will.
- Hansel and Gretel from Black Lagoon. Despite being underage siblings, their relationship is the only humanising thing about them.
- Hunt and Sarah from Tegami Bachi.
- Tono to Issho: Oda Nobunaga fell in love with Nohime because she was prepared to stab her father in the face without hesitation.
- In Puella Magi Oriko Magica, the villains behind the magical girl murderers are Oriko and Kirika, who have at least a strong Romantic Two-Girl Friendship, but more likely a couple, especially according to Kirika. They even end up Together in Death.
- Barbara and Lotten, the two antagonists of the Crashtown Arc in Yu-Gi-Oh! 5D's, 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, using seduction and her beauty to do so.
- In Kekkaishi, this is implied to be the relationship between Byaku and 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.
- In Akuma na Eros, a girl named Miu makes an odd Deal with the Devil with Satan - the price being her virginity. Therefore, it looks like the story is heading towards them pulling this. It does. Oddly, what Miu truly needed to be Satan's bride was dying; when she's murdered by Satan's Clingy Jealous Girl Sara, she becomes able to leave her former life as a human and rule with him in Hell.
- The Maoh King and Parome in Genma Wars. They are a demon couple that rules over a post-apocalyptic earth and serve as the primary antagonists. Subverted in that while they are bound by marriage, its completely loveless: the Maoh King is extremely unfaithful preferring to take several human females as concubines, which makes his wife Parome extremely bitter. In the end, Parome and her husband end up killing each other.
- While not married to each other, Doctor Strange 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 Marvel Universe Evil Counterpart to the Fantastic Four (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 She-Hulk.
- During the Infinity event, we are introduced to Corvus Glaive and Proxima Midnight, two members of Thanos' Black Order who are Happily Married. They are shown to be supportive of each other both on and off the battlefield. If not for their roles as Thanos' Generals and love of killing, they would be the rare non-dysfunctional married Marvel couple.
- Fantastic Four 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.
- Even earlier, The DCU has the Sportsmaster and the Huntress/Tigress, two Golden Age villains revealed to have married when they returned in the 1960s.
- Harley Quinn puts quite a lot of effort into persuading The Joker to enter into this joyous state, but has only gone so far as Mad Love, 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.
- Death of the Family: Poison Ivy and Clayface are now husband and wife. This may seem odd, but it makes sense when one considers that she's a plant lady and he's a pile of clay (which is a part of the earth), and plants and earth go together just fine! It was a ploy for Ivy, to use Clayface as bait for some plan
- From the always reliably warped Doom Patrol, we have a rare gay example: The Brain, a disembodied brain who occasionally has a robotic body, and his Dragon Monsieur Mallah, a hyperintelligent French Marxist gorilla.
- In Captain America, the Red Skull'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 Big "NO!".
- In the Crime Syndicate, the Mirror Universe version of the Justice League of America, Superwoman (evil Wonder Woman) is married to Ultraman (evil Superman). But she's contemptuous of her husband, and her illicit affair with Owlman (evil Batman) is closer to the trope.
- In Archie Comics' Sonic the Hedgehog, there's Scourge and Fiona Fox. Fiona pulled a Face–Heel Turn to be with him, and when Scourge took over 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 thankfully were just a marriage of political convenience. The Queen did, however, have a thing on the side with Snively, and while each seemed to be using each other to advance their positions in Eggman's empire, there was also clearly some geniune affection there.
- During Stilt-Man's funeral, it's revealed that he and Princess Python from the Circus of Crime had been married.
- Judge Dredd: Played with when the Dark Judges brainwash a woman to become a helpless slave so they can use her as a psychic bridge to Mega City One to start their Necropolis. In her dreams they hold a mock ceremony where she elopes with Judge Death (who's a walking corpse, by the way) and affirm the unholy matrimony by murdering her actual husband. As soon as she outlives her usefulness, they kill her.
- Gold Digger: Sherisha and Gothwrain serve as a counterpoint to the numerous good Battle Couple around. A pair of incredibly old wererat assassins who rule the criminal underworld and have been married only slightly less long than weres have been around, which shows in their incredible teamwork.
- The New 52 Flash series has Sam Scudder (Mirror Master) and Lisa Snart (Glider) as a couple before they got their powers and Lisa was a criminal (she knew Sam through her brother Captain Cold). After they receive their powers and Glider embraces her family's lifestyle, this trope is in full effect.
- In the Marvel Universe, there's Viper, a high-ranking and sometimes leader of HYDRA, and Silver Samurai, a Heel–Face Revolving Door (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.
- Beyond Birthday and Light Yagami in That Epic Plan:
"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 Those Who Stand for Nothing Fall for Anything 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. Ryuk and L have some of this going, too.
- In the remake of Yu-Gi-Oh! The Thousand Year Door (but not the original) the Shadow Queen has been officially married twice.
- Her second marriage was a loveless one of convenience to Count Bleck, who is Vladimir's father. He plays a role in the fic of a secondary villain, trying to usurp her rule of Arcadia and trying to win his son from her in a demented parody of a custody battle.
- Her first marriage, to the man she truly loved, was to Lyrius, the Queen's Shadow. He was killed in the original battle a thousand years ago, but his failure to protect her resulted in him lingering on as a phantom. He was given a temporary pseudo-life in the second half of the book, becoming The Dragon for all intents and purposes, and survives the ending, making a Heel–Face Turn at the sponsoring of a higher power. Plans are in the works for a Spin-Off that feature him as the star, likely one where his goal is undertaking an Orphean Rescue to save his beloved's soul from Graz'zt.
- Dark!Harry and Voldemort in Harry Potter and the Descent into Darkness. After Dark!Harry helps Voldemort get his body back they instantly take a liking to each other.
- Voldemort and Bellatrix Lestrange in A Very Potter Musical.
- You could also say in a Ho Yay sense for Voldemort and Quirrell, especially since later in the play 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.
- Trixie and Prince Blueblood in story 2 of the My Little Pony: Friendship Is Magic fanfic Legion of Gloom. Not only is their dating considered one of the Squickiest things in the fic in-universe, their marriage ceremony is...well...
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 Homestuck to be portrayed this way. Hivefled uses Deliberate Values Dissonance to crank up the villainy; they're moirails, and so by the standards of their society are supposed to be Platonic Life Partners 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 Ask a Pony blogs Discorderly Conduct and Cupidite, in their frequent crossovers, portray Discord and Queen Chrysalis as having had a relationship long ago. It... didn't end well, and is strongly implied to be the Start of Darkness for both of them.
- Arzt and Nie, witch assassins of Resonance Days, are a very, very intimate couple, who often talk about how their arrival in the afterlife is proof that love conquers all. Most other characters find them saccharine or creepy (and the uncanny resemblance doesn't help). To a lesser extent, the Madam, a brutal crimelord, and Margot, her Battle Butler, have a very close relationship and enjoy nuzzling when not finding inventive ways to torture people who can't die.
- In the Naruto and Soul Eater Crossover fic He'll Never Be My Son, Orochimaru and Medusa seem very happy together, as romantic partners and Evilutionary Biologists helping each other out.
- In the final story of the My Hostage Not Yours series, Zim and Gaz — who transition from Anti Heroes to full Villain Protagonists — get married a while after taking over North America, and end up honeymooning in Europe after that's conquered as well.
- In A Charmed Life Ryuk and Light shack up together in the Shinigami realm.
- Alena from The Swarm of War is called the Overmind's Queen-consort. Chapter 60 shows it's more than just a formal title.
- This is the entire premise of the fic My Dark King—Jack and Carly both turning evil and ruling what's left of the world, while maintaining their love for each other.
- Some Fullmetal Alchemist fans like to pair up the manga's Big Bad, Father with the 2003 anime's Big Bad, Dante. The fact that they actually have quite a lot in common certainly helps. Here's a particularly hilarious example.
- For perhaps one of the most horrifying examples possible, this image pairs up Maleficent with the Slender Man!
Film — Animation
- Scar and Zira from The Lion King II: Simba's Pride, even if this relationship is off-screen.
- In South Park: Bigger, Longer & Uncut, Satan is in a gay relationship with Saddam Hussein, though the later is negligent and at times verbally abusive while Satan is 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 Minions, Scarlet and Herb Overkill have a very loving relationship.
- Chucky and Tiffany from the Bride of Chucky and Seed of Chucky are vicious murderers, but love each other... most of the time.
- In Austin Powers: The Spy Who Shagged Me, Dr. Evil and Frau Farbissina have a fling, leading to The Reveal that Scott Evil is their love child, thanks to some fun with a
- Before that/after that, Frau Farbissina gets involved with a female professional-golfer-assassin.
- Sol and Viper, the fun-loving cannibal couple in Doomsday.
- The Mummy Returns had Imhotep reunite with a reincarnated Anck Su Namun in an unhealthily undead version of Reincarnation Romance. 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 Collapsing Lair falls around them and the hero couple. He extends his hands to her for help, and she... leaves. Imhotep turns to the O'Connell's (where Evie did help Rick up) and gives them a heartbreaking smile before letting go. Anck Su Namun got punk killed shortly afterwards.
- The Crow: Wicked Prayer: Luc Crash and Lola Byrne are this trope, and are, by all indications, genuinely in love. Then they go through with their Unholy Wedding Ceremony, and Luc gets possessed by Satan...
- The Mayflowers, the Card Carrying Villains of the deliciously campy Hudson Hawk, are passionately in love with one another in a way that makes them more villainous and creepy.
- The only time Darwin loses his Psychotic Smirk is when Minerva is horribly killed by a splash of molten lead.
- Magneto and Mystique of X-Men. However, it is thoroughly broken by X-Men: Days of Future Past, where they try to kill one another.
- Riff-Raff and Magenta from The Rocky Horror Picture Show.
- Cosmo and Nation McKinley from Shock Treatment.
- In Foxy Brown, the main villain is Katherine Wall, who runs a combined call girl and drug empire. Steve Elias is The Dragon 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.
- Running Scared (2006): There's a particularely depraved example in a husband and wife who kidnap children, then molest them, videotape it, and kill them. However, it's ambiguous whether they love each other or if they bonded over their shared proclivity.
- Averted in Batman Returns during The Penguin and Catwoman's brief partnership. While he would like this trope to happen, she has no romantic or sexual interest in him whatsoever, and turns down his advances both times he comes on to her. After the second time, he spitefully tries to kill her, but she gets better.
- In Natural Born Killers, Mickey and Mallory begin their romance by murdering her parents and eloping on a nation-wide killing spree.
- Bibok and Calosta in Esther Friesner's Majyk By Design. 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. 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 Conan the Barbarian story, The People of the Black Circle, a villainous sorcerer was convinced by his lover that he should betray his four masters and Take Over the World on his own. He was actually able to use The Power of Love 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 lives just long enough to give Conan information on how to kill them.
- Odiana and Aldrick in Codex Alera. 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 about the horrible violence they are perfectly willing to inflict on anyone else.
- Harry Potter:
- 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; 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 (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 Heel–Face Turn.
- Vernon and Petunia. They're selfish and abusive to Harry, yet they seem quite devoted to each other and their biological son.
- This is exactly what goes on between Voldemort and Bellatrix Lestrange...in the latter's twisted and hopeless dreams.
- Now confirmed due to the introduction of Delphini, daughter of Bellatrix and Vodemort in Harry Potter and the Cursed Child.
- Dangerous Liaisons 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 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 make a temporary Heel–Face Turn, 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, it's debatable whether they still love each other, or ever did. Caine lies to Diana and uses her for sex, and 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".
- Norman and Sandra Arminger from the 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.
- The Dresden Files:
- Esteban and Esmeralda Batiste, nicknamed "The Eebs", are a husband/wife assassin team for the 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 also has Duchess Arianna, an ancient 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. She loved him enough to plot elaborate revenge upon his death.
- Which is nothing compared to the lovely activities Nicodemus Archleone and his wife Tessa come up with.
- This is outright stated in Skin Game with regards to Nicodemus and Deirdre, daughter of Nicodemus and Tessa. Yes, that means exactly what it sounds like. The relationship between Nicodemus and Diedre became incredibly twisted and disturbing and at the same time quite genuine. Toward the end of the book, Harry is even able to use the disturbing love between the two to cause Nicodemus to go into full Villainous Breakdown after he sacrifices Diedre to get into Hades' vault.
- Esteban and Esmeralda Batiste, nicknamed "The Eebs", are a husband/wife assassin team for the Red Court. Susan thinks that their relationship is romantic in an incredibly warped and psychotic way.
- Black-magic users Isaac and Selena Izzard in John Bellairs' The House With a Clock in Its Walls, although they're both dead by the time the story starts.
- 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 Two-Faced top enforcer. They are 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.
- In Death 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 Moral Event Horizon...if s/he has not already done so!
- Sisterhood Series by Fern Michaels: 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, as 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 Skulduggery Pleasant has a twisted affection for Tanith Low, but it was only when 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 Those That Wake's sequel, Arielle and Roarke are close, and implied to be romantically linked.
- 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. 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.
- In Carrie, Billy and Chris (although not actually married, since they're still in high school) qualify. Put the two most sociopathic teens in town together....
- The Addams Family is more Affably Evil than outright villainous, but Moricia and Gomez's relationship could technically qualify as this. They are a very loving couple, and their show is one of the few sitcom-style series on TV without marital strife as a running gag.
- The Buffyverse:
- 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.
Cordelia: Imagine Bonnie and Clyde if they had 150 years to get it right.
- Likewise, Spike and Drusilla, who seemed to be genuinely in love, albeit still murderous. 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 work quite so well and doesn't last nearly so long, for more than one reason.
- Lindsey and Eve; she even gave up her immortality and role as liaison to the Senior Partners for him.
- Harmony and Hamilton, although that didn't last long.
- Vampire Willow and Vampire Xander, much to Cordelia's exasperation. Besides killing people, their relationship involves Xander watching Willow brutally torture people.
- 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.
- Charmed: Quite literally—if someone wants to remain aligned with Evil in marriage, it must be performed by a Dark Priest at night in a cemetery.
- Chinese Paladin: Used as a means of demonstrating The Power of Love when the heroes find a snake- and fox-demon couple preying on travelers. The snake-demon sacrifices his physical form to save his wife, who then pledges to devote herself solely to preserving his soul. Unfortunately, the hero doesn't know about that, and kills her, too.
- Criminal Minds: Anita and Roger Roycewood, the couple of child abductors and murderers.
- Criminal Minds showed a range of UnSubs with couple dynamics. One was a young couple on a whirlwind romance who went on a spree pf revenge killings, another was an older married couple who had been killing runaways and hookers for decades and even underwent couples counselling.
- 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.
- Hercules: The Legendary Journeys and Xena: Warrior Princess: Over the course of both shows, Ares has been romantically involved with both Callisto and Hope, even impregnating the latter.
- House of Cards (UK): 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 gain someone's trust. She knows all of his devious acts (including the murders) and they conspire and live together happily.
- Same applies to House of Cards (US).
- Lois and Clark: Had a rich Sickeningly Sweethearts couple who kept their marriage alive by brewing evil plans together.
- The Middleman: Vlad and Lizzie, the vampire couple.
- The New Statesman: 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 "love-hate relationship" to whole new levels...)
- Nikita: It's eventually revealed that Amanda is in a secret alliance/relationship with Ari Tasarov; together, they plot against both the protagonists and their respective superiors, in order to gain more control and power for themselves. Even after their master plan fails 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 Evil Counterpart to the one between Nikita and Michael.
- Power Rangers:
- In Mighty Morphin' Power Rangers, Lord Zedd and Rita Repulsa actually went as far as subverting the inevitable failure of the Love Potion—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 Moral Guardians 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 Space Pirate Divatox wanted to release Maligore in the Power Rangers Turbo movie. She started having second thoughts after getting a good look at him, seeing that he is a berserk fire demon.
- In Power Rangers Zeo 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.
- Revolution: As of 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. Episode 10 shows that Tom would surrender before he sacrifices Julia. 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.
- Spartacus: Blood and Sand:
- Batiatus and Lucretia have a great and loving relationship, but are the Big Bad 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 of Seppia, whose corpse is still floating in the pool next to them.
- True Blood: Russell Edgington and Steve Newlin. Slow-dancing to Katy Perry in a frat house full of bodies they've fed and murdered, flirting while glamouring 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, in a sociopathic way.
- The Vampire Diaries: Inverted Trope: Damon loves Katherine but she's more interested in his little brother.
- Daredevil: Wilson Fisk (A.K.A. The Kingpin) meets art museum curator Vanessa and falls in love with her. After going on a date and learning just who he really is, she falls in love with him. She supports him unquestionably as our hero Matt Murdock tries to tear down Fisk's empire. At the end of the first season, he proposes to her literally as he's being dragged away by the FBI.
- On Mr. Robot, Corrupt Corporate Executive Tyrell Wellick and his wife are this. He sleeps with a male secretary in order to further his career and she is implied to know about it. They also go to dinner with the head of Evil Corp in order to secure him the CTO position. When Tyrell's intimidation tactics fail to get him the position, she simply tells him to try again.
- Maddalena and Gareth from Galavant. He brings her a present of earrings—with the previous owners' ears still attached. For his birthday, she starts a war with a neighboring kingdom.
- The Ax-Crazy couple in "A Little Piece of Heaven" by Avenged Sevenfold.
- Precisely 50% of the songs on Seanan McGuire album Red Roses and Dead Things involve this trope with varying degrees of creepiness.
- "Lucifer" by Blutengel.
- A lot of Ordo Rosarius Equilbiro's work fits this trope. Especially "Do Lust and Murder Make Me a Man?" and "Let the Words of My Murder Be the Last Words You Hear."
- "Killers in Love" by Tub Ring.
Mythology and Religion
- Older Than Feudalism with Classical Mythology:
- Typhon and Echidna. She's a beautiful woman with the lower body of a snake, and a fondness for eating travelers. He's a giant with one hundred dragon heads, and a tendency towards deicide. Together they sired the Hellhounds Orthrus and Cerberus, the Chimera, the Nigh Invulnerable Nemean Lion, the Sphinx, the massive eagle that eats Prometheus' liver, and the nearly-unkillable Hydra. It becomes even better if you realize that among the Greek pantheon they're probably the two deities/monsters/primordial beings 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 someone like Zeus, who, to say the least, Really Gets Around. Truly a match made in Tartarus (who is, coincidentally, their father).
- Neither Hades nor Persephone were really evil (despite popular belief), but both were feared by the ancient Greeks, seeing as they ruled the afterlife, and were generally dark beings (yes, Persephone too, in her role as Queen of the Underworld). Their marriage may have been based on kidnapping at first, but, if nothing else, Hades was far more faithful than the average god.
- In the Big Finish Doctor Who audio drama "The Next Life", Zagreus and Daqar Keep become this at the end.
- Parodied in Bleak Expectations: When Harry Biscuit has a Face–Heel Turn from Mr Benevolent's mind-control, Pippa turns evil as well because she thinks a couple should share their hobbies and turns out to be much better at it than him, so that when he becomes good again, she becomes Mr Benevolent's Evil Consort. In the following season Harry undergoes another Face–Heel Turn under the influence of an evil pen, and this time Pippa is only pretending to be evil in order to stay with him.
- Played with earlier than that. Mr. Benevolent turns good and marries his childhood love, Sweetly Delightful... except on their honeymoon he tells her all about his evil deeds, and she gets interested in the idea. From the way Benevolent describes it, he'd turned evil again for her, but by the time the honeymoon was over he'd lost interest, and was only going along with it for the sake of the henchmen.
- From 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 The Empire. 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 Emergency Transformation. She took it amazingly well.
- In gameplay, if you have both on the table and one of them is killed, the other 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.
- With the End Times, Vlad was returned to life as a Mortarch. However he's more than a little miffed that not only was Isabella not revived, but apparently they didn't go to the same afterlife. He's now only following Nagash, who is hellbent on turning the world into an undead paradise, so that Nagash will revive Isabella for him.
- Dungeons & Dragons:
- Count Strahd Von Zarovitch believes that 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 Ironic Hell 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 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.
- There was also the rather...twisted relationship between the Evil Sorceress Iggwilv and the demon lord Graz'zt; they were lovers for a time, he helped her forge an empire, and she bore his son, who would grow up to be the cruel tyrant Iuz...all despite the fact that she had technically kidnapped him and was holding him prisoner. It ended very badly. (Oddly enough, while some sources have claimed that Graz'zt has killed minions for simply bringing it up, a Fourth Edition write-up on Graz'zt claims that Iggwilv is his "ally and occasional lover". Of course, given how chaotic demons are, anything is possible.)
- From Deadlands fluff, we have Miles and Mina Devlin: ruthless railroad barons, dark sorcerers, devoted spouses and loving parents. After Miles' assassination, things go downhill.
- In the Giantslayer adventure path in Pathfinder, the main villain for the first part of the module, Skreed, is an evil alchemist that is in love with a mercenary that he met when trying to recruit followers in a bid to conquer human civilization. The two carry magical lockets that tell each the current physical status of the other. Their love is genuine; should Skreed die in the first part (which is extremely likely, as he fights to the death), his lover attempts to get vengeance in the second part of the module.
- Mr. and Mrs. Mao Zedong are largely portrayed as a loving and romantic, if occasionally disturbing couple. The song "The Chairman Dances" is dedicated to this trope.
- Sweeney Todd: The Demon Barber of Fleet Street: Sweeney Todd and Mrs. Lovett has shades of this, even though they're not married and she's the only one who wants a Relationship Upgrade.
- Monsieur and Madame Thénardier in Les Misérables. 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 Twelfth Night, Toby and Maria spend a lot of time together preparing Batman Gambits in order to make fools of others, and sure enough, at the end of the play we find out that they've eloped.
- Macbeth: The title character is married to his Dragon Lady Macbeth. Probably the most famous example, and even has a subtrope named after it.
- Baldur's Gate has a few examples:
- Sarevok, the Big Bad of the first game, has two relationships on the go—the first with a Kara-Turan woman called Tamoko, the other with a woman called Cythandria. Cythandria is in love with him because of his capability as a villain, but Tamoko is an odd case—she seems to love him in spite of his evil rather than because of it, and wants him to abandon his Evil Plan to stay with her instead.
- To confront and expose Sarevok late in the game, the characters first have to get an invitation to his inauguration ceremony 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 families are driving them apart since they're a bad influence on each other. One of your options is to be a Love Freak 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 Outlaw Couple and are now robbing people in your name.
- Viconia can be redeemed to True Neutral if you romance her as a good guy, but you can also romance her as an evil character and she'll happily play the role of Lady Macbeth, supporting and encouraging your godly ambitions.
- A romance with Dorn Il-Khan is this in the extreme, and can lead to either Bash Brothers or a Dark Lady and Black Knight match-up, since Dorn is blatantly bisexual.
- Romancing 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 Viconia—both of whom are evil.
- Your own parents were this. Your father was Bhaal, the Lord of Murder, who planned to either sacrifice his children or set them on each other as part of a Thanatos Gambit. 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.
- Alice and Decus of Tales of Symphonia: Dawn of the New World, with the "one playing the other" thing (gender-flipped). When Decus becomes a Love Martyr, that changes everything...
- Oda Nobunaga and Nouhime in Sengoku Basara. Nobunaga is an Evil Overlord, while Nouhime is his Love Martyr Psycho Supporter. On Nouhime's death, Nobunaga deems her worthless.
- Nobunaga and Nouhime have a similar relationship in Samurai Warriors 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 they are attracted with each other's carnage lust.
- Overlord gives you a choice in Mistresses, though there's always one that's actually relatively non-evil and arguably the Only Sane Person in this Crapsack World. First game featured the prim and proper Rose and the greedy and slutty Velvet. The second game (which confirms Rose as the canon choice) offers Victorious Childhood Friend Kelda, Gold Digger Juno and Fallen Hero Dark Fay.
- Subverted in World of Warcraft, 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 Face–Heel Turn. 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 Lady and Knight vibe going on about them. As of the fourth expansion, this evolved into an Alas, Poor Villain scenario. Mograine had 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 The Remnant of the (in)famous Scarlet Crusade, this time with Commander Durand to replace Mograine for gameplay purposes. But what really sells it are Whitemane's Famous Last Words following her allegedly final defeat:
- Malygos and Saragosa. Killing Saragosa and then taunting Malygos over Saragosa's corpse earned the red dragon Keristrasza a Fate Worse Than Death at the hands of a berserk Aspect of Magic. And then death, too, in The Nexus.
- Lady and Killer from Shadow Hearts: From the New World. Though whether the latter was actually in love or merely Mind Controlled is debatable.
- In Knights of the Old Republic, Bastila suggests this possibility to a male Player Character near the end. 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 Neverwinter Nights Hordes of the Underdark.
- If you pick the evil path in Neverwinter Nights 2 Mask of the Betrayer, the player and Gann or Safiya (depending on gender).
- Before it was cut, an evil female player and Bishop in Neverwinter Nights 2.
- Certain mods do have examples, including Vico and the player in A Dance with Rogues and Alex and the player in The Bastard Of Kosigan.
- 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 Tales of Monkey Island Chapter 5: Rise of the Pirate God, using his Voodoo powers from 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, when, after LeChuck breaks free from prison and saves Guybrush and Elaine after the cure of the Pox of LeChuck, he tells our hero that "it was the only way to win Elaine's hand in unholy matrimony"...confusing him and allowing LeChuck to make a clever, fatal ambush on him.
- Catherine: In one of the Multiple Endings, 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 Happily Married.
- Soltier and Lapis of Blaze Union. This, along with the fact that they're Anti Villains, helps to earn them Redemption Equals 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 Resident Evil 2 seem to be a happily married couple of scientists. Mad Scientists!
- Black Scorpion and Silver Mantis seem to have this sort of relationship in City of Heroes.
- Traffic Department 2192. 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 Knights of the Old Republic games mentioned above—it comes as no surprise that the MMO Star Wars: The Old Republic 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 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 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 caring 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-canon ending of Mortal Kombat II, she is a "secret partner" with Baraka. They both kill Shao Kahn and take over the Outland, ruling it as king and queen.
- The Elder Scrolls V: Skyrim has Astrid and Arnbjorn of the Dark Brotherhood, two assassins who happen to be married.
- Dynasty Warriors from 5 onwards has an example in the couple of Cao Pi and Zhenji. She is a sadistic Lady Macbeth, he is the ambitious, cold-as-ice successor to the Throne of Wei. Together, they 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 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 antiheroic way.
- Interestingly, this is quite a divergence from the 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 wouldn't play well with a contemporary audience.
- Done very humorously at the end of Super Mario RPG. Booster proposes to Valentina in Marrymore, and she says "yes"; however, he 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 Borderlands 2, Big Bad Handsome Jack is in an active and happy relationship with Nisha, the Sheriff of Lynchwood. He's a fascist, megalomanical Mega Corp. dictator intent of wiping out everyone who he considers a "bandit". She's a psychopathic Blood Knight who gets off on hurting people and being hurt right back. They're a perfect match. Borderlands: The Pre-Sequel! shows how they eventually got together if you play as Nisha, with her gradually becoming more and more attracted to Jack as he slides down the slope and becomes more and more violent and ruthless. She outright admits that she's in love when Jack 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 The Sims 2, this is heavily implied with Circe and Loki Beaker of Strangetown. Loki is a Mad Scientist 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.
- In Umineko: When They Cry, it turns out this is the case between Bernkastel and Lambdadelta, who have similar circumstances and would both do anything to stave off boredom. The latter is rather Ambiguously Evil though.
- In Hate Plus, Ryu and Oh Eun-a.
- Caster and Kuzuki Souchirou in Fate/stay night.
- Villain Protagonists Fuminori Sakisaka and Saya from Saya no Uta.
- In the webcomic Cheshire Crossing—which is essentially a Massive Multiplayer Crossover between The Wizard of Oz, Alice in Wonderland, Peter Pan and Mary Poppins, 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 *intimate* partnership. This also effectively turns her into a witch-pirate, or maybe pirate-witch, which is awesome. Pirate.
- In The Order of the Stick, 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 through black magic and human sacrifice. And 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.
- During a Flashback sequence in General Protection Fault, it's revealed that Trudy—chessmaster and Puppetmaster extraordinaire—had a "team-up" 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 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.
- Minions at Work: Leading up to it.
- Narbonic: Dave and Helen, eventually.
- Axel and Aerith in Ansem Retort. 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.
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 Kevin & Kell, 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...girlfriend in xkcd.
- Brian and Angelo in Our Little Adventure.
- Didi and Gogo in Fine young cannibals by VanHeist, inspired by Sweeney Todd. Aren't they a cute pair?
- Occurs between Mad Scientists Spencer Ecchs and Ada Byon in Patchwork Champions. 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 Sluggy Freelance, it looked like Crushestro and Monicruel were heading this way, until Chestro, his real wife, arrived. If she's not 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. 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.
- Jadis the White Witch in the Mega Crossover Fan Webcomic-verse Buildingverse is prone to have such relationships. Her ex in the backstory of Roommates is the Erlkönig and she is currently together with Darkness the Prince of Darkness in Girls Next Door (her son from the first relationship doesn't need enemies: he has two parents from hell and a stepfather he loathes with passion).
- Girl Genius had a rather hilarious scene when two Ax-Crazy characters finally found each other. Bangladesh DuPree suffered instant infatuation with Vole upon hearing a bloodthirsty visionary rant from this walking death machine. She even dropped Tarvek whom she tried to torment at the time.
- Also, according to Castle Heterodyne, protagonist Agatha's ancestors Dagon Heterodyne and the Skull-Queen of Skral were an example as well.
- Jack Noir and the Black Queen from Homestuck are a weird version of this. Specifically, they are considered to be in a kismesissitude, a sexual relationship based around hatred.
- In CKarrus Ton Shi and Xylla are both not nice people with plans to murder the hero, but they are also a lovingly married couple. Doesn't mean they are always nice to each other though.
- Subverted in L's Empire. While Dark Star and Phala had each been the Big Bad at one point, Phala had undergone a Heel–Face Turn by the time that they hook up.
- Some examples in the Whateley Universe, natch. Some of the Bad Seeds (a clique you can only join if at least one of your parents is a supervillain) go to 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.
- Worm has a very creepy example in Night and Fog, neo-Nazi supervillains who act out the role of a married couple with so little emotion or deviation from the routine that even their teammates find it disturbing.
- Pokemon Pals: Apparently Jesse and James are married. James wanted to steal pikachu to rekindle a spark in their relationship.
- Critical Role has Sylas and Delilah Briarwood, the couple that killed Percy's family. They are a vampire and a necromancer, respectively, and they are conducting a ritual that could bring an extremely evil god into the word. They are also happily married and deeply in love, to the point where some of the party members were visibly upset after seeing Delilah's reaction to them killing Sylas.
- In the Transformers Animated 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 Kick the Dog 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.
- Kim Possible:
- 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...
- The Grand Finale gives Drakken and Shego an implied Last Minute Hookup... but it's not clear whether they will continue to be villains after being hailed for helping to save the world from an Alien Invasion.
- One episode of Care Bears 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 Gargoyles, Xanatos and Fox make for an Affably Evil—or, after their shared Heel–Face Turn, Affably Magnificent—couple. The fans love 'em.
- Azula tries to invoke this with Chan, a guy she meets at a party in the Beach/Villain Episode of Avatar: The Last Airbender, openly stating that she plans to conquer and rule with him by her side. Since Chan is a Jerk Jock but not a power-mad despot, he's predictably terrified.
- Sequel Series The Legend of Korra gives us a very genuine and almost sweet example with the Affably Evil Empowered Badass Normal Zaheer and the towering, aloof, and volatile-in-more-ways-than-one Dark Action Girl P'Li. While Bolin is captured by them, he hints that long-haired, incongruously jovial lavabending Ghazan and Handicapped Badass water-and-ice Ming-Hua have an unspoken attraction. They don't (and never do) confirm it, but they share an awkward look with each other.
- Former Metal Clan guard captain turned dictator Kuvira is planning on marrying one of the Beifong Spin-Offspring, who also seems to be her second-in-command. Until she blasts the building he's in with a spirit laser in an attempt to kill Korra. He survives, but it's pretty clear their relationship is over after this.
- On 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 Rocky and Bullwinkle.
- Another one (which arguably fits the Happily Married Trope more than any other example on this list) is The Venture Bros.'s The Monarch and Dr. Mrs The Monarch (seriously), pictured above. They get married at the end of the second season (before which she's Dr. Girlfriend) and become an officially licensed supervillain team at the start of the third season.
- Johnny 13 and Kitty from Danny Phantom
- In 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, other story materials affirm the No Hugging, No Kissing 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 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 once she's Queen he becomes expendable...
- In El Tigre 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 Squicky as Puma is human while Sartana is a walking skeleton. Word of God says that they had a son together, though their relationship was on and off.
- Destro and The Baroness from G.I. Joe. 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 Phineas and Ferb featured Mad Scientist Doofenshmirtz dating a woman just as evil as he was. They even got a song together, though the relationship unfortunately doesn't work out, thanks to Doof's Evil Plot of the Week coming back to bite him in the butt.
- In the Second Dimension, it turns out that Charlene is also evil, and the two are still married.
- Anti-Cosmo and Anti-Wanda on The Fairly Oddparents. Possibly also a subversion, as Anti-Cosmo doesn't seem to be particularly happy in the arrangement.
- Mac and Molly Mange of SWAT Kats. They were powerful gangsters and married before they 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 older fans of Wild Kratts sense a bit of Belligerent Sexual Tension between Zack Varmitech and Donita Donata; they even went out on a date in canon. Although, if there is any actual attraction, it seems one-sided on Zach's part.
- Chief from Pucca, head of the local Quirky Miniboss Squad, has a crush on Garu's enemy Tobe. In one episode they became this trope after Tobe got 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 Captain Planet and the Planeteers, Dr. Blight and her assistant MAL have a weirdly flirty relationship in the early seasons, though it becomes more Like an Old Married Couple in later seasons. She has also been known to flirt with Looten Plunder, though he seems Oblivious to Love.
- Darkstar and Charmcaster in one episode of Ben 10: Ultimate Alien. Of course, Darkstar being 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 doesn't end well for him when she finds out the truth...
- Moral Orel: 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 Oedipus Complex and the latter due to having been "castrated" as a child.
- Fred's real parents in Scooby-Doo! Mystery Incorporated.
- In South Park, Saddam Hussein and Satan, though most of their in-series appearances are after they break up. See above in "Films—Animated".
- In Earthworm Jim, Evil the Cat gets a girlfriend in Malice the Dog, his Distaff Counterpart. Unfortunately for him, she has to leave for another universe when she gets offered a star role in her own TV show.
- In Xiaolin Showdown, it was highly hinted that Chase Young and Wuya were this.
- Codename: Kids Next Door had one-shot villain duo Mega-Mom and Destructo-Dad. They're Chad Dickson (f.k.a. Numbuh 274)'s parents.
- The Mummy: The Animated Series: Anck-Su-Namun is even worse in the Animated Adaptation. 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 Artifact of Doom 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 And I Must Scream state.