History Main / CreepyCrossdresser

27th Jan '16 10:20:15 AM Willbyr
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* [[EvilTwin Rosiel]] from ''AngelSanctuary'' often [[IncrediblyLamePun skirts]] the line with his... ''[[FashionVictimVillain unusual]]'' [[FashionVictimVillain outfits]]. AntiVillain [[{{Bifauxnen}} Belial]] also counts.
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* [[EvilTwin Rosiel]] from ''AngelSanctuary'' ''Manga/AngelSanctuary'' often [[IncrediblyLamePun skirts]] the line with his... ''[[FashionVictimVillain unusual]]'' [[FashionVictimVillain outfits]]. AntiVillain [[{{Bifauxnen}} Belial]] also counts.

* Count D in ''PetshopOfHorrors'' is good friends with a group of drag queens and transvestites, and his peacocks also appear this way in their 'human' forms.
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* Count D in ''PetshopOfHorrors'' ''Manga/PetshopOfHorrors'' is good friends with a group of drag queens and transvestites, and his peacocks also appear this way in their 'human' forms.
24th Jan '16 9:51:05 AM Morgenthaler
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[[quoteright:350:[[Film/TheDarkKnight http://static.tvtropes.org/pmwiki/pub/images/nolan5.png]]]]
13th Jan '16 12:53:02 PM StFan
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[[folder:Anime}} and {{Manga}}]]
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[[folder:Anime}} and {{Manga}}]][[folder:Anime & Manga]]

[[folder:ComicBooks]]
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[[folder:ComicBooks]][[folder:Comic Books]]

[[folder:FanWorks]] * ''Manga/{{Evangelion 303}}'': Saburo starts to cross-dressing as part of a plan to win Kaworu back. However Kaworu finds it creepy and unsettling. * A ''Webcomic/{{Homestuck}}'' fanart calendar featured a badly-crossdressing [[TheCaligula Eridan Ampora]] in the [[http://abortedslunk.deviantart.com/art/Homestuck-Calendar-March-Page-191184591 March page]] as a joke. The "March Madness" outfit caught on and became a fandom meme, even [[AscendedMeme making a cameo appearance in the Ministrife updates]].
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[[folder:FanWorks]] [[folder:Comic Strips]] * ''Manga/{{Evangelion 303}}'': Saburo starts to cross-dressing as part of Sanjak from ''ComicStrip/TerryAndThePirates'' is a plan to win Kaworu back. However Kaworu finds it creepy and unsettling. * A ''Webcomic/{{Homestuck}}'' fanart calendar featured a badly-crossdressing [[TheCaligula Eridan Ampora]] in the [[http://abortedslunk.deviantart.com/art/Homestuck-Calendar-March-Page-191184591 March page]] as a joke. The "March Madness" outfit caught on and became a fandom meme, even [[AscendedMeme making a cameo appearance in the Ministrife updates]].rare female version.

[[folder:{{Film}}]]
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[[folder:{{Film}}]][[folder:Fan Works]] * ''Manga/{{Evangelion 303}}'': Saburo starts to cross-dressing as part of a plan to win Kaworu back. However Kaworu finds it creepy and unsettling. * A ''Webcomic/{{Homestuck}}'' fanart calendar featured a badly-crossdressing [[TheCaligula Eridan Ampora]] in the [[http://abortedslunk.deviantart.com/art/Homestuck-Calendar-March-Page-191184591 March page]] as a joke. The "March Madness" outfit caught on and became a fandom meme, even [[AscendedMeme making a cameo appearance in the Ministrife updates]]. [[/folder]] [[folder:Films -- Animation]] * Snatcher performs as Madame Frou Frou to spread fear of ''WesternAnimation/TheBoxtrolls''. [[/folder]] [[folder:Films -- Live-Action]]

* ''Film/AceVenturaPetDetective'': The titular detective gets particularly grossed out when he learns that the "woman" he kissed earlier in the film is actually a guy who had [[DisguisedInDrag stolen the identity]] [[DeadPersonImpersonation of a missing hiker]]. -->'''Ace Ventura''': Einhorn is Finkle...Finkle is Einhorn! EINHORN IS A MAN! ''({{beat}})'' [[OhCrap OH MY GOD!]] [[UnsettlingGenderReveal EINHORN IS A]] ''[[UnsettlingGenderReveal MAN?!]]'' ** Pretty much ''everybody else'' (yes, ''even the '''dolphin''''') is just as grossed out when Ace reveals it, in fact.
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* ''Film/AceVenturaPetDetective'': The titular title detective gets particularly grossed out when he learns that the "woman" he kissed earlier in the film is actually a guy who had [[DisguisedInDrag stolen the identity]] [[DeadPersonImpersonation of a missing hiker]]. -->'''Ace Ventura''': Ventura:''' Einhorn is Finkle...Finkle... Finkle is Einhorn! EINHORN IS A MAN! ''({{beat}})'' (''{{beat}}'') [[OhCrap OH MY GOD!]] [[UnsettlingGenderReveal EINHORN IS A]] ''[[UnsettlingGenderReveal MAN?!]]'' ** :: Pretty much ''everybody else'' (yes, ''even the '''dolphin''''') is just as grossed out when Ace reveals it, in fact.

* MichaelCaine in ''{{Film/Dressed to Kill}}''.
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* MichaelCaine in ''{{Film/Dressed to Kill}}''.''Film/DressedToKill''.

* {{Deconstructed}} and PlayedForLaughs in ''AustinPowers'': ''International Man Of Mystery''. Austin is used to spotting and de-wigging evil assassins disguised as women, as befitting a {{Camp}}y TuxedoAndMartini spy flick, essentially rendering him WrongGenreSavvy in TheNineties. This leads to him knocking back Basil's poor mother and trying to pull her wig off. * ''Film/TheBoondockSaints'' - Detective Smecker (Willem Dafoe) gets a little too into character when dressing drag to infiltrate a mob manor. So do the Mook guards.
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* {{Deconstructed}} and PlayedForLaughs in ''AustinPowers'': ''Film/AustinPowers'': ''International Man Of Mystery''. Austin is used to spotting and de-wigging evil assassins disguised as women, as befitting a {{Camp}}y TuxedoAndMartini spy flick, essentially rendering him WrongGenreSavvy in TheNineties. This leads to him knocking back Basil's poor mother and trying to pull her wig off. * ''Film/TheBoondockSaints'' - ''Film/TheBoondockSaints'': Detective Smecker (Willem Dafoe) gets a little too into character when dressing drag to infiltrate a mob manor. So do the Mook guards.

* In ''{{Film/Shine}}'', David (it's implied) sleeps with one while he is studying in the Royal College of Music. * In ''{{Literature/Filth}}'', [[spoiler:the main character]] is this, although, frankly, he's creepy independently of this habit and the actual crossdressing is played for sympathy.
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* In ''{{Film/Shine}}'', ''Film/{{Shine}}'', David (it's implied) sleeps with one while he is studying in the Royal College of Music. * In ''{{Literature/Filth}}'', ''Literature/{{Filth}}'', [[spoiler:the main character]] is this, although, frankly, he's creepy independently of this habit and the actual crossdressing is played for sympathy.

* Snatcher performs as Madame Frou Frou to spread fear of ''WesternAnimation/TheBoxtrolls''.

[[folder:Folklore}}]]
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[[folder:Folklore}}]][[folder:Folklore]]

[[folder:{{Literature}}]]
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[[folder:{{Literature}}]][[folder:Literature]]

* Bbelle from ''{{Literature/Malevil}}''. Part of it is being creepy and evil, another part is using DisguisedInDrag to infiltrate settlements prior to his marauding army invading.
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* Bbelle from ''{{Literature/Malevil}}''.''Literature/{{Malevil}}''. Part of it is being creepy and evil, another part is using DisguisedInDrag to infiltrate settlements prior to his marauding army invading.

[[folder:LiveActionTV]]
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[[folder:LiveActionTV]][[folder:Live-Action TV]]

[[folder:Newspaper Comics]] * Sanjak from ''TerryAndThePirates'' is a rare female version.
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[[folder:Newspaper Comics]] [[folder:Pro Wrestling]] * Sanjak from ''TerryAndThePirates'' is a rare female version.Harvey Whippleman as "Harvina" won the WWF Women's Championship, and Santino Marella's [[PaperThinDisguise identical twin sister]] "Santina" won the Miss WrestleMania battle royale.

[[folder:ProfessionalWrestling]] * Harvey Whippleman as "Harvina" won the WWF Women's Championship, and Santino Marella's [[PaperThinDisguise identical twin sister]] "Santina" won the Miss WrestleMania battle royale. [[/folder]]

[[folder:{{Webcomics}}]]
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[[folder:{{Webcomics}}]][[folder:Web Comics]]

[[folder:WebOriginal]]
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[[folder:WebOriginal]][[folder:Web Original]]

* As another plan to get in WebVideo/ToddInTheShadows's pants, WebVideo/TheNostalgiaChick tied [=SadPanda=] to a chair, stole his clothes and pretended (poorly) to act like him.
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* Website/ThatGuyWithTheGlasses: ** As another plan to get in WebVideo/ToddInTheShadows's pants, WebVideo/TheNostalgiaChick tied [=SadPanda=] to a chair, stole his clothes and pretended (poorly) to act like him.

[[folder:WesternAnimation]]
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[[folder:WesternAnimation]][[folder:Western Animation]]

6th Jan '16 11:51:52 PM ironcommando
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* ''VideoGame/PlantsVsZombies2ItsAboutTime'': In the Zombot Multi-Stage Masher fight, Dr Zomboss stands on a stage and changes his clothes to fit the current Jam. During the Pop Jam, he dresses up like a popstar girl with a dress and red wig. Take note that Zomboss is a diminutive male zombie with an [[MyBrainIsBig oversized brain]].
5th Jan '16 2:07:56 AM jormis29
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* In ''VideoGame/SaintsRow 2'' the player can dress their character in any clothes in the game, regardless of gender. So the player can make their character a transvestite, or even a {{Transsexual}} through EasySexChange, if they so desire. * TheMedic in ''VideoGame/TeamFortress2'', sort of. He has [[AndYourRewardIsClothes an unlockable wig]] that's in a geisha style with a comb and small flowers, leading to a BrokenBase over those who thought Valve was pandering to the fans who wanted more HoYay (not all crossdressers are gay and not all gays crossdress, guys). If you know your history, geishas were originally all male. Regardless, it's a compliment. It's a ''VideoGame/ShogunTotalWar''-inspired item, and geisha are some of the most badass units in that game.
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* In ''VideoGame/SaintsRow 2'' ''VideoGame/SaintsRow2'' the player can dress their character in any clothes in the game, regardless of gender. So the player can make their character a transvestite, or even a {{Transsexual}} through EasySexChange, if they so desire. * TheMedic in ''VideoGame/TeamFortress2'', sort of. He has [[AndYourRewardIsClothes an unlockable wig]] that's in a geisha {{Geisha}} style with a comb and small flowers, leading to a BrokenBase over those who thought Valve was pandering to the fans who wanted more HoYay (not all crossdressers are gay and not all gays crossdress, guys). If you know your history, geishas were originally all male. Regardless, it's a compliment. It's a ''VideoGame/ShogunTotalWar''-inspired ''VideoGame/TotalWarShogun2''-tie-in item, and geisha are some of the most badass units in that game.
3rd Jan '16 11:50:00 AM nombretomado
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* Kanan of ''SoulNomadAndTheWorldEaters'', according to Vitali. [[spoiler:Penn in the Demon Path]] counts as well. * ''FinalFantasyTacticsA2'': The Night Dancer is a cross-dressing CampGay ''[[LizardFolk Bangaa]]''. He even wears lipstick (on a Bangaa!) and eyeshadow and refers to himself as female, but fights with him tend to be fought under the "No harming the opposite sex" law, which outs him as male by the fact that female characters attacking him break the law while male characters attacking him do not. (On the other hand, some are so convinced by his insistent female identification that they really believe that he's a she and the law identification is a bug.) [[http://www.youtube.com/watch?v=ibhXqRhxaTU]]
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* Kanan of ''SoulNomadAndTheWorldEaters'', ''VideoGame/SoulNomadAndTheWorldEaters'', according to Vitali. [[spoiler:Penn in the Demon Path]] counts as well. * ''FinalFantasyTacticsA2'': ''VideoGame/FinalFantasyTacticsA2'': The Night Dancer is a cross-dressing CampGay ''[[LizardFolk Bangaa]]''. He even wears lipstick (on a Bangaa!) and eyeshadow and refers to himself as female, but fights with him tend to be fought under the "No harming the opposite sex" law, which outs him as male by the fact that female characters attacking him break the law while male characters attacking him do not. (On the other hand, some are so convinced by his insistent female identification that they really believe that he's a she and the law identification is a bug.) [[http://www.youtube.com/watch?v=ibhXqRhxaTU]]
2nd Jan '16 10:21:01 AM nombretomado
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* Dark from 2002's ''Film/HuntingHumans''. As SomethingAwful put it:
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* Dark from 2002's ''Film/HuntingHumans''. As SomethingAwful Website/SomethingAwful put it:
11th Nov '15 8:33:43 PM kazokuhouou
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* [[spoiler: Angela]] turns out to be one in the infamous TwistEnding of the SlasherMovie ''Film/SleepawayCamp''.
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* [[spoiler: Angela]] turns out to be one in the infamous TwistEnding of the SlasherMovie ''Film/SleepawayCamp''. To be fair though, [[spoiler: it got forced onto Angela/Peter by a demented aunt.]]
11th Nov '15 8:31:28 PM kazokuhouou
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* In ''Film/{{Beyond the Valley of the Dolls}}'', the character [[spoiler:Ronnie 'Z-Man' Barzell goes on a murderous, drug-induced rampage dressed as "Superwoman"]]
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* In ''Film/{{Beyond the Valley of the Dolls}}'', the character [[spoiler:Ronnie 'Z-Man' Barzell goes on a murderous, drug-induced rampage dressed as "Superwoman"]]"Superwoman". Then again it's unclear if Z-Man really is this trope or is actually trans, considering this scene followed Z-Man revealing female breasts to Lance.]]
18th Oct '15 9:50:26 PM CaptainCrawdad
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* ''Film/TheToxicAvenger'': One of the two thugs in Cigar Face's street gang is a cross dresser in a dress, wig and make-up. While the Toxic Avenger is ripping his buddies apart, the cross dresser stands aside to reapply his make-up before joining the fray.

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* ''Series/MrRobot'': An apparent bigwig in the Dark Army, a mysterious hacker mercenary organization, is dressed as a woman during his brief meeting with the hero. It's never commented on, and in a later scene he wears a classic men's tuxedo, possibly implying that he was deliberately using the trope to mess with the hero's head.
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