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* ''Literature/ChildOfGod'': [[spoiler:After Lester becomes a full-on serial killer, he starts wearing the clothes of his female victims. At first it comes across as Lester, a homeless man who lives primarily in caves at this point, wearing any clothes he can get his hands on, but towards the end of the book it's mentioned that he made at least one wig out of a scalp.]]
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* In ''Film/NightAfterNightAfterNight'', the SerialKiller [[DisguisedInDrag disguises himself in drag]] to evade the police after he is almost caught, and the presence of wigs, makeup and women's clothing in lair indicates that this is not a new activity for him.
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* In ''Film/NightAfterNightAfterNight'', the SerialKiller [[DisguisedInDrag disguises himself in drag]] to evade the police after he is almost caught, and the presence of wigs, makeup and women's clothing in his lair indicates that this is not a new activity for him.
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* ''Manga/DeadmanWonderland'' had an AntiHero example in the form of Choplin "Peacock" Sukegawa, who was a mix of this and WholesomeCrossdresser. He was a gay man in a relationship with a bisexual GoldDigger and after being bullied by his coworkers over his sexuality, upon finding his boyfriend cheating on him with a woman he snapped, accidentally [[MurderTheHypotenuse killing her]] with his BloodMagic. After being sent to prison he began [[DrivenByEnvy dressing like the woman he killed out of envy for her good looks]], but aside from that was rather personable for a death row inmate.
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* ''Manga/DeadmanWonderland'' had an AntiHero example in the form of Choplin "Peacock" Sukegawa, who was a mix of this and WholesomeCrossdresser. He was a gay man in a relationship with a bisexual GoldDigger and after being bullied by his coworkers over his sexuality, upon finding his boyfriend cheating on him with a woman he snapped, accidentally [[MurderTheHypotenuse killing her]] with his BloodMagic. After being sent to prison he began [[DrivenByEnvy dressing like the woman he killed out of envy for her good looks]], but aside from that was rather personable for a death row inmate. [[spoiler:By the end of the story he drops the "creepy" part entirely, having [[CharacterDevelopment found the confidence to adopt his own identity instead of hijacking someone else's]].]]
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* ''Manga/DeadmanWonderland'' had an AntiHero example in the form of Choplin "Peacock" Sukegawa, who was a mix of this and WholesomeCrossdresser. He was a gay man in a relationship with a bisexual GoldDigger and after being bullied by his coworkers over his sexuality, upon finding his boyfriend cheating on him with a woman he snapped, accidentally [[MurderTheHypotenuse killing her]] with his BloodMagic. After being sent to prison he began [[DrivenByEnvy dressing like the woman he killed out of envy for her good looks]], but aside from that was rather personable for a death row inmate.
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* In a ''WesternAnimation/KingOfTheHill'' ChristmasEpisode, StrawLoser Bill's seasonal depression stemming from his ex-wife [[TheLostLenore Lenore]] leaving him worsens to the point he's DrivenToSuicide. After a series of shenanigans with the gang [[BlackComedy foiling multiple attempts]], he has a nervous breakdown and out of a desperate desire to reconnect with his wife starts trying to act like her, putting on a dress and speaking in a high-pitched voice like a fat, balding Norman Bates. He later crashes Hank's Christmas party during this, and the other {{Good Ol Boy}}s in attendance get the wrong idea and start harassing him under the belief he's some pervert, until Hank saves the day by putting on a dress himself to play it all off as a joke.
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* Music/NewYorkDolls played up this image by wearing trashy women's clothing on stage.
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* Dr. Frank N. Furter from ''Film/TheRockyHorrorPictureShow''. Also a DepravedBisexual, not that anyone's complaining.
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* Dr. Frank N. Furter from ''Film/TheRockyHorrorPictureShow''. Also a DepravedBisexual, not that anyone's complaining. An unusual example of the trope because his crossdressing isn't portrayed as disgusting or ugly in itself (though it shocks the more sheltered characters); instead, it's treated as part of what makes him so attractive and charismatic, with his attractiveness and charisma in turn being used to manipulate and abuse people. (Creator/RichardOBrien, the writer of the film, is queer and a crossdresser himself, and accordingly created the character as [[EvilIsCool someone to either envy or be attracted to]] rather than purely someone to be horrified by, depraved though he is.)
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* Another notable game example is the villain Alfred Ashford, from ''VideoGame/ResidentEvilCodeVeronica''. He not only dresses in drag to pose as his own sister, but has an irritatingly mincing laugh and an extreme hatred towards the female protagonist, Claire.
** Plus, he has an obsession for the BigBad that could be taken as a crush, despite the fact that [[spoiler:the BigBad is his sister]].
** Plus, he has an obsession for the BigBad that could be taken as a crush, despite the fact that [[spoiler:the BigBad is his sister]].
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** Plus,
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* Dr. Frank N. Furter from ''Film/TheRockyHorrorPictureShow''. Also a DepravedBisexual, [[EvilIsSexy not that anyone's complaining.]]
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* Dr. Frank N. Furter from ''Film/TheRockyHorrorPictureShow''. Also a DepravedBisexual, [[EvilIsSexy not that anyone's complaining.]]
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* In ''Film/OnTheBuses'', Mavis assumes Blakey is wearing frilly pants and a black suspender belt under his mac when she believes he has tried to steal her friend's knickers.
