Villainous Crush / Live-Action Films

• In 12 Years a Slave, slave owner Edwin Epps has one on his slave Patsey. Word of God says he's deeply in love with her, but he has an odd and very abusive way of showing it.
• 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 Babes in Toyland (1934), the Laurel and Hardy version.
• Biff from Back to the Future for Lorraine. He constantly hit on her when they were in high school and intended to make her his date for a dance even when she vehemently rejected his advances. Things only get worse in Part 2 where he murders George and marries Lorraine in another timeline.
• Barbarella: The evil Black Queen is determined to get in Barbarella's skirt/shorts, though when she keeps rejecting her (sometimes quite violently), she'll settle for her angelic ally Pygar.
• Joker for Vicki Vale in Batman (1989). He even murders his previous squeeze to "make himself available".
• While we're at it, the Riddler seems to have a bit of one on Chase Meridian in Batman Forever — when he's not crushing on Bruce Wayne, that is.
• In Batman & Robin, Poison Ivy seems in love with Robin, seducing him in every encounter and flirting heavily with him, even promising to change sides so they can be together and help guide him to be his own man. However, this is all actually subverted, as Poison Ivy was not actually in love with Robin and was only trying to separate him and Batman and kill him with her Kiss of Death, and once that fails to kill him she angrily shoves him away from her to have her plants drown him. Poison Ivy actually has a crush on Mr. Freeze, another villain, and attempts to kill his wife so she can have him for herself.
• Black Mask from Birds of Prey (2020) has one for his singer-turned-driver Dinah Lance, keeping her as close as possible and invading her personal space.
• The titular character in Blackway is the violent crimelord antagonist of the film, and seems to harbor an obsession for the heroine, Lillian. He meets her at the restaurant she works at and tries to get a date with her, but she rejects him. He waits for her to get off work and then tries to rape her in the empty parking lot, but she gets away. Following this incident, he begins following her and even decapitates her cat to get her attention. Lillian tries to go to the sheriff of their small Northwest logging community to help her get Blackway to leave her alone, but he implies that Blackway has immunity because of his corrupt influence.
• Blade Runner 2049 has Wallace's dragon-replicant Luv being heavily hinted at having this towards K. She compliments him and tries to question him on personal matters right after K said that's a way to tell someone likes another person. The way it plays makes it seem like Luv is making a earnest attempt to flirt with. Later she plants a "Take That!" Kiss on him. That also gives her destroying Joi's emitter a Murder the Hypotenuse vibe. Especially since she lets K live, despite having killed every other person she's come across to cover her trail.
• In Bram Stoker's Dracula ancient vampire Dracula becomes obsessed with young English woman Mina Murray and wants to transform her into his bride. In order to do it he traps Mina's fiancee in his castle, finds and stalks Mina in London, and then finally sneaks into her bedroom to drink from her and make her drink his blood.
• In Cabin by the Lake, Villain Protagonist Stanley seems to develop some sort of odd fixation on his victim Mallory for standing up to him and escaping him once before. There's a Window Love scene with a two-way mirror which she punches when she realizes what he's doing, and when he tries to drown her once again near the end he also starts to lean in for a kiss as she's terrified out of her mind.
• Cruz Diablo: Old man Marquiss Pedro of Florida asked Diego de la Barrera for the hand of his young daughter. It's later revealed he aided in the murder of the actual Count of Luna, Marcela's actual father.
• Ramon Rojo from A Fistful of Dollars has one on Marisol, keeping her away from her husband and son with the excuse that the former owes him money.
• Fist of the North Star: Shin is enamored by Julia, but she preferred her beloved Kenshiro, whom Shin then tried to kill to have her for himself. She spitefully rejects his every advance while he doggedly keeps offering her the world.
• Ming the Merciless seemed pretty hung up on Dale Arden in Flash Gordon.
• In the film version of Gone Girl, it's open to interpretation, but the relationship between Nick and Amy could be considered this, as could the relationship between Amy and Desi.
• A comedic version in The Great Muppet Caper when jewel thief Nicky Holiday falls head-over-heels in love with Miss Piggy.
• J.D. in Heathers. After Veronica breaks up with him after he starts murdering other teenagers for fun, J.D. is still very much in love with her.
• Aldrich Killian for Pepper Potts in Iron Man 3.
• 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 (albeit slightly ambiguously) offers her the chance to stay with him and be loved by him if she gives up her quest.
• Legend (1985): Darkness, the devilish baddie, has one on Princess Lili, explicitly because of her pure soul.
• The Lord of the Rings: The Two Towers: King Théoden's Evil Chancellor Gríma Wormtongue has a big one on the king's beautiful, proud niece, Éowyn (it's suggested in the books as well, but the film plays it up).
• In The Mask of Zorro, Don Rafael was the original Zorro's rival for Esperanza. When his plan to get rid of his enemy ended up killing Esperanza, he took in her daughter as his own.
• Midsommar: Pelle has a crush on Dani, as shown by his looking at her from afar, making portraits of her, and kissing her near the end of the film.
• Tod to Marge in Mom and Dad Save the World.
• The Mooring: This low-budget horror movie has an Axe-Crazy Big Bad hunting a group of technology-addicted tweens (their trip was a rehabilitation program). He occasionally shows some Pet the Dog moments to some of the girls but still murders all of them via different means, except the Final Girl whom he had earlier shown an, uh... interest in. When he finds her sobbing uncontrollably (due to having witnessed the death of her friends, being terrified out of her mind etc.) he just cradles her and tries to assure her "he isn't going to hurt her". It is easily the most unsettling scene in the whole movie if only because it shows how terrifyingly insane he is.
• In Never Grow Old, Dutch's hulking and mute henchman Dumb-Dumb develops a disturbing obsession with Patrick's wife Audrey.
• Ned to Julie in The Next Karate Kid. He punishes her if she rejects his advances.
• Patrick Still Lives: The title character seems to have one for Lydia, as demonstrated in a scene where he attempts to telekinetically lift her skirt up.
• 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.
• Prom Night (2008): The film's events started off with Evil Teacher Richard Fenton lusting after his student Donna Keppel. Things escalated quickly, with Fenton being fired and a restraining order filed against him. He responded by murdering Donna's parents and brother; he is arrested and sent to a mental institution. Three years later, he's broken out and infiltrates the prom, intent on murdering everyone Donna cares about so the only person left in her life is him.
• Rippner, a psychopathic assassin, to Lisa, the main protagonist, in Red Eye.
• Schindler's List. Nazi Camp Kommandant Amon Goeth has one on Helen Hirsch, his Jewish maid. This leaves him conflicted because he believes her to be inferior to him.
• The Scorpion King: Memnon is attracted to his beautiful sorceress Cassandra, whom he intends to marry and make her his queen after his conquest over the land is complete. The only reason he hasn't already is because she will lose her visions if she loses her virginity. Cassandra's ancestors spread the fiction that their powers are tied to their virginity precisely to keep men like Memnon from taking advantage of them.
• In Shredder Orpheus, the EBN producer has eyes for Eurydice, much to her disgust, and it's implied Persephone is attracted to Orpheus, which is part of why she convinces Hades to let him go and call him back a year later.
• Dark Helmet for Princess Vespa in Spaceballs, from what you can tell in the scene where he plays with his action figures.
• Spiders II: Breeding Ground: Captain Bigelow wants to have Alexandra for himself and is more than happy to have her fiance die by giving him to Dr. Grbac. When she discovers his real motives, she makes her feelings abundantly known.
• Star Wars:
  • In Return of the Jedi, Jabba the Hutt captures Leia, forces her into a metal bikini, and keeps her as his right-hand slave before eventually trying to kill her love interest Han and all her friends.
  • The Star Wars sequel trilogy exhibits this through the interactions of Kylo Ren and Rey.
    • In The Force Awakens, he takes her for the map's contents instead of taking BB-8—who has the literal and physical map inside of him. He even carries Rey away bridal-style. By contrasting Poe and Rey's interrogations, it is obvious Kylo Ren is much more gentle with Rey, going as far as showing her his face. Snoke even picks up on it in the adult novelization by accusing Kylo Ren of having compassion for her.
    • The Last Jedi makes it a lot less ambiguous: he’s definitely got feelings for her, talking to and empathizing with her through their Force Bond, killing Snoke to save her, and asking her to rule at his side. Rey, herself, seems to return these feelings after Character Development, despite her rejecting his offer and their “break up” by the end of the film. This relationship, on Kylo Ren’s part, serves to highlight his humanity and the tragic conflict of his character.
    • The Rise of Skywalker makes it canon, but only after he turns from the Dark Side, reclaiming his identity as Ben Solo. They share a Big Damn Kiss before his untimely death from having resurrected her by transferring his life energy to her.

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