Villainous Crush

"Just fear me. Love me. Do as I say, and I shall be your slave."

- Jareth the Goblin King to Sarah, Labyrinth

So, The Hero's girl is pretty cute. Only it turns out the Hero isn't the only one who thinks so. She's caught the villain's eye as well.

If this crush takes a turn for the perverse, this can lead to tropes like I Have You Now, My Pretty, Forceful Kiss, Bathe Her and Bring Her to Me, And Now You Must Marry Me, Scarpia Ultimatum, and Go-Go Enslavement, although none of those require a Villainous Crush. Additionally, the villain may become a Stalker with a Crush. If the crush itself is a motivating factor in his Start of Darkness, then it's Love Makes You Evil.

Conversely, this trope can be played as a humanizing factor, making the character into more of an Anti-Villain, and the love interest may act as a Morality Pet. Taken all the way, it may become Love Redeems.

Despite the description, this trope applies whenever a villainous character has feelings for a heroic one, not just when the Big Bad has the hots for the Hero's girlfriend. That's just usually the way it goes.

If the feelings are mutual or an actual relationship develops, then it's Dating Catwoman instead. When this is purely subtextual, see Foe Yay. The specific variant when the Evil Empress captures the hero to seduce him is Villainesses Want Heroes.

Anime & Manga

 * Road towards Allen in D.Gray-man. She even kisses him at one point.
 * In episode 4 of Meitantei Holmes, Professor Moriarty kidnaps Mrs. Hudson to get to Holmes, but she's so kind that he soon develops a serious crush on her himself. When the plan eventually fails, he releases her and promises never to involve her in one of his schemes again.
 * The whole deal in Inuyasha would have NOT started if the thief Onigumo didn't fall in love with Kikyou, then made a Deal with the Devil that transformed him into none other than Naraku...
 * Also from the same series, Jakotsu towards Inu-Yasha himself, and Mukotsu towards Kagome.
 * Happens more than once in Sailor Moon, where villains of both genders were attracted either to Usagi (Seijuuro/Alan, Prince Diamond) or to Mamoru (Queen Beryl, Natsumi/Anne, manga!Dark Lady, anime!Fish Eye, anime!Nehelenia).
 * Sorta used in Shaman King, where Hao is pretty pleased when Yoh's Action Girl fiancée Anna Kyouyama stands up to him...
 * Vampire Hunter D. Vampire lord Count Magnus Lee desires the human girl Doris Lang, but she only has eyes for the title Hero.
 * Elie from Rave Master. Everybody's got a crush on her, even the psycho Lucia, who stole her first kiss, leaving her in tears.
 * Rido from Vampire Knight was obsessed with his sister Juri and then subsequently with
 * Voltron: Lotor has a very unrequited obsession with Allura.
 * It continues in the American-produced Sequel Series, Voltron Force.
 * Outlaw Star: Harry towards Melfina.
 * Full Metal Panic!: Gauron towards Sousuke and Leonard towards Kaname.
 * Mobile Suit Gundam ZZ: Haman Khan seems to have one of these on Judau Ashta, while Glemmy Toto has one on Roux. In each case the heroic individual ends up being responsible in some way for their admirer's death.

Comic Books

 * Rather infamously in Spider-Man Sins Past, Norman Osborn took a shine to Gwen Stacy. And by that it means he
 * In Marvel comics, the villain Whirlwind has a huge crush on The Wasp. He even posed as her limo driver once.
 * Umar, Doctor Strange villainess and sister to Dormammu has a huge crush on The Hulk. She actually kept him as her love-slave for a while, but whether that counts as Dating Catwoman or Black Comedy Rape is debated. They've been reunited since.
 * In his short lived series in the 70s, The Joker fell in love with one Dinah Lance. He realizes he only has two choices, force her to marry him or kill her because he won't be able focus on his crimes if he's thinking about her.

Film

 * Gaston to Belle from Beauty and the Beast
 * Frollo to Esmeralda in The Hunchback of Notre Dame
 * Beaumont for Madeleine in White Zombie.
 * Ming the Merciless seemed pretty hung up on Dale Arden in Flash Gordon.
 * Mr. Barnaby (the Crooked Little Man) for Contrary Mary (or Mary Contrary, in the Disney version) in Victor Herbert's Babes in Toyland and the analogous Little Bo-Peep in March of the Wooden Soldiers, the Laurel and Hardy version
 * Subverted in The Princess Bride. It appears that Prince Humperdinck is in love with Buttercup, but it turns out that he just wants to marry her so he can arrange for her to be killed and then use her death to justify a war with the scapegoats.
 * Dark Helmet for Princess Vespa in Spaceballs, from what you can tell in the scene where he plays with his action figures.
 * Rippner to Lisa in Red Eye.
 * Joker for Vicki Vale in Batman.
 * While we're at it, the Riddler seems to have a bit of one on Chase Meridian in Batman Forever.
 * Blue for Baby Doll in Sucker Punch.
 * Jareth to Sarah in Labyrinth. Foreshadowed in Sarah's story to Toby at the beginning: "But the Goblin King had fallen in love with the girl..." He sends her into a dreamlike state featuring a Dance of Romance between them, and at the end, he offers her the chance to stay with him and be loved by him if she gives up her quest.
 * Similarly, Darkness seems to develop a distinct interest in Princess Lili in Legend, going so far as to Corrupt the Cutie enough that she will be willing to dally with him.
 * Tod to Marge in Mom and Dad Save The World
 * Megamind on Roxanne since before the events of the film, as confirmed by the filmmakers' commentary.

Literature

 * Edgar Rice Burroughs' Thuvia, Maid of Mars. Carthoris is in love with the title character, who is also desired by the Villain, Prince Astok of Dusar.
 * Another Burroughs' example would be At the Earth's Core, in which Hooja the Sly One lusts after David Innes's beloved Dian the Beautiful.
 * The Phantom's obsessive infatuation with Christine in The Phantom of the Opera. Leads to Stockholm Syndrome on Christine's side and ends with I Want My Beloved to Be Happy on the Phantom's side. The narrator pities him more than condemns him.
 * And the Phangirls love him.
 * William Hamleigh for Aliena in The Pillars of the Earth, although that's more of a Perverse Villainous Obsession variant.
 * Billy "Boil" seems to have one on the titular heroine of the Cat Royal series of books, although how much of a villain he is varies from book to book.
 * Littlefinger for Catelyn Stark, later  Heavily implied to be his Start of Darkness.
 * Burgo Fitzgerald for Glencora M'Cluskie and George for Alice Vavasor in Trollope's Can You Forgive Her?.

Live-Action TV

 * Davis Bloome on Chloe in Season 8 of Smallville. Sometimes Tess Mercer seems to have one on Clark. And then there was the whole Lex/Lana mess in Seasons 5 & 6, and Lionel's unrequited crush on Martha which ran for most of the show.
 * Unfortunately for Kurt on Glee,.
 * Ares has it bad for Xena: Warrior Princess, to the point where his motivation throughout the show is basically to win her love.
 * There were indications in Season Two that how Lord Zedd felt about Kimberly in Mighty Morphin Power Rangers was not just Foe Yay subtext, especially with the episode he tried to make her his queen.
 * Either played extremely, scarily straight or averted in Sherlock with James Moriarty and Sherlock Holmes. Moriarty originally presented himself as a camp gay when he was undercover to get to Sherlock, but once he dropped the "Jim from IT" face, the act remained. The two flirt incessantly in an impressive display of villainous UST.
 * On Luther the titular detective has to deal with the uncomfortable fact that his closest friend and confidante, and most reliable source of help is Nietzsche Wannabe Manipulative Bastard and thorough psychopath Alice Morgan. That alone would be bad enough, but as many of Alice's lines suggest, she may well have a thing for Luther.

Roleplay

 * Before being sealed away for good, Apos had a downright disturbing fascination with User:Ozbourne.

Tabletop Games

 * Shadowrun adventure Harlequin's Back. In the Backstory, a Horror fell in love with Queen Thayla and refused to leave her, even though his presence was destroying her land. She eventually decided to leave with him to save her people from destruction.

Theater

 * Judge Turpin of Sweeney Todd: The Demon Barber of Fleet Street developed two of these. The first was on Sweeney's wife, Lucy Barker, which ultimately led him to kick off the plot by having Sweeney transported for life, followed by luring her to a masked ball and raping her. The second was on Sweeney and Lucy's daughter Johanna, who he adopted out of remorse for what he did to Lucy but came to desire as more than a daughter as she grew older, leading him to have her thrown into a madhouse upon learning that she planned to elope with Anthony Hope, a young sailor. Sweeney finally takes vengeance upon Turpin by

Videogames

 * Darth Sion of Knights of the Old Republic II developed an interest in the female Exile immediately after seeing her; his crush was so intense, it was threatening his connection to the Dark Side, and therefore his life.
 * Bowser to Peach. Especially in Paper Mario.
 * Hell, it's even a major plot point in Super Paper Mario.
 * Super Mario Odyssey even more so, where he tries to force her to marry him.
 * LeChuck to Elaine in the Monkey Island series.
 * Combined with Les Yay in Shantae. Big Bad Risky keeps oscillating between threatening our heroine and trying to flirt with her.
 * Final Fantasy X: Seymour Guado has one on Yuna, resulting in a Forceful Kiss. Made squickier by the fact that Yuna shares a voice actress with Seymour's mother.
 * Apparently, Trabant had some feelings for Ethlin. Too bad she was Happily Married to Cuan.
 * Mix this with Yandere, Complete Monster, I Have You Now, My Pretty, and Dragon Rider, and you have Valter the Moonstone.
 * Valkyrie Profile: Lezard is fascinated by Lenneth and would do anything to get her for himself. The fans don't mind though.
 * Kain is jealous of his best friend Cecil for winning the heart of Rosa, the apple of his eye. Does he Murder the Hypotenuse? Thankfully, no. Kain is ultimately accepting of his status as the Unlucky Childhood Friend and hides his feelings for Rosa out of respect for the trio's deep friendship. Unfortunately, Dark Kain does not value his better half's reservations, even going as far as to pull an I Have You Now, My Pretty moment when he captures Rosa in The After Years.
 * Poison towards Cody in Final Fight Revenge.

Webcomics

 * Sinfest's Fuchsia/Criminy romantic subplot started out when the seductive succubus Fuchsia took an interest in Criminy for the purpose of corrupting his innocence. When he treated her kindly, she was reminded of her humanity and developed a crush on him. They gradually started spending more time together, leading to positive Character Development for both of them, as Fuchsia genuinely tried to become the good girl she thought Criminy would like, while Criminy came out of his shell, matured, and arguably Took a Level in Badass for her sake.
 * Galgarion from RPG World apparently has some crush on Cherry.
 * A spoileriffic but amusing one from Homestuck:
 * In Girl Genius, maybe Zola was faking weakness every time Gil had to rescue her, but her love for him remains after she revealed being way more dangerous than she looks.
 * Depending how you interpret him, Tarvek may be this (crush undisputed, villainy not certain). And even Gil, but he's rather an Anti-Hero.

Web Originals

 * Dr. Horrible, of his eponymous sing-along blog, has a crush on a local do-gooder, but his arch-nemesis hero beats him to the punch. Unusually, Dr. Horrible is more of a Well-Intentioned Extremist, while the so-called hero is an arrogant bully who only dates the girl to make the protagonist jealous.

Western Animation

 * Ty Lee to Sokka in Avatar: The Last Airbender, much to Sokka's confusion
 * In the "Super Powers Team" incarnation of Superfriends, Darkseid had a crush on Wonder Woman and constantly tried to make her his bride.
 * One time on The Simpsons Marge got a job at the nuclear plant and Mr. Burns developed a thing for her.
 * A 1935 Merrie Melodies short, "The Little Dutch Plate'', where it is rather creepily subverted.
 * Hexadecimal to Bob in Re Boot.
 * Zander to Max in Batman Beyond.
 * Peep to Heloise in Jimmy Two-Shoes. Heloise to Jimmy may also count.
 * Tobey McCallister to Word Girl. He doesn't even try to deny it anymore.
 * One-shot villain Little Acorn to Jenny in My Life as a Teenage Robot.
 * Martian Queen towards Duck Dodgers. Seriously, the woman veers between wanting to destroy him and wanting to marry him.
 * In the animated version of The Incredible Hulk, Gargoyle had a crush on She-Hulk and was constantly trying to woo her; sadly for him, she was never interested.
 * The G.I. Joe: A Real American Hero episode "The Gamemaster" not only hints that Zartan has something like this towards Scarlett, but that she reciprocates it!
 * In one episode of Teen Titans, Red X flirted with Starfire after pinning her to the wall with one of his gadgets, calling her "cutie" and remarking that the "only crime" between them was that they hadn't gone on a date. Her only response was to blast him with her starbolts through her eyes.
 * Pyro once tried making a pass at Rogue in the X-Men cartoon. She replied by throwing him through the wall as a non-subtle "No".

Real Life

 * During the Libyan Civil War it was discovered that Muammar Gaddafi had one on former US Secretary of State Condoleezza Rice, no less. The rebels even found a sizable photo album full of pictures of her in his compound.
 * Apparently, this wasn't a surprise for her; diplomatic meetings with him were apparently quite awkward.