History Main / CreepyCrossdresser

18th Apr '16 6:27:27 PM SomberCaelifera
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*** In an effort to help Buster overcome his low self-esteem and be more assertive with his mother, Tobias dresses up in Lucille's clothes; including her underwear. It [[RuleOfFunny doesn't even]] [[MakesJustAsMuchSenseInContext make sense in context]].

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*** ** In an effort to help Buster overcome his low self-esteem and be more assertive with his mother, Tobias dresses up in Lucille's clothes; including her underwear. It [[RuleOfFunny doesn't even]] [[MakesJustAsMuchSenseInContext make sense in context]].
11th Apr '16 12:22:12 PM Piando
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* ''WebVideo/TenLittleRoosters'' episode 3 has Miles [[spoiler:running around, wearing Lindsay's [[WebOriginal/{{RWBY}} Ruby Rose]] cosplay dress, complete with make up and lipstick.]]

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* ''WebVideo/TenLittleRoosters'' episode 3 has Miles [[spoiler:running around, wearing Lindsay's [[WebOriginal/{{RWBY}} [[WebAnimation/{{RWBY}} Ruby Rose]] cosplay dress, complete with make up and lipstick.]]



* In ''WesternAnimation/BatmanTheBraveAndTheBold'' TheJoker disguises himself as an Amazon to try and kill WonderWoman.

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* In ''WesternAnimation/BatmanTheBraveAndTheBold'' TheJoker SelfDemonstrating/TheJoker disguises himself as an Amazon to try and kill WonderWoman.Franchise/WonderWoman.
4th Mar '16 10:48:37 PM Pichu-kun
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** The androgynous but genuinely male Envy has traits of this which were especially played up in the English dub, where his voice is more feminine.
*** This only applies in the 2003 anime, however, as Envy in the manga has no gender (or, according to [[WordofGod Word of God]], no one knows Envy's true gender not even Envy). So whether or not they have one is up for debate. If they do, they're as lost as we are.
** Barry the Chopper (anime version), who dresses as a woman when out delivering meat from his butcher shop.

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** The androgynous but genuinely male Envy has traits of this which were especially played up in the English dub, where his voice is more feminine.
***
feminine. This only applies in the 2003 anime, however, as Envy in [[Manga/FullmetalAlchemist the manga manga]] has no gender (or, according to [[WordofGod Word of God]], no one knows Envy's true gender not even Envy). So whether or not they have one is up for debate. If they do, they're as lost as we are.
** The serial killer Barry the Chopper (anime version), who dresses first appeared dressing as a woman when out delivering meat from his butcher shop.shop. He kidnapped Winry and [[WouldHurtAChild almost murdered]] both her and Edward.



** Team Rocket, most of the time: Jessie would crossdress as a male (complete with mustache), while James crossdressed as a female at the same time. Perhaps the most disturbing example is the infamous "bikini contest" episode. Amusingly, no reason was ever given why they couldn't just disguise themselves as their own gender.

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** Team Rocket, most of the time: In Kanto and Johto, Jessie would crossdress as a male (complete with mustache), while James crossdressed as a female at the same time. Perhaps the most disturbing example is the infamous "bikini contest" episode. Amusingly, no reason was ever given why they couldn't just disguise themselves as their own gender.


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* [[spoiler:Marube]] from ''Manga/{{Yuureitou}}'' is obsessed with [[IJustWantToBeBeautiful becoming beautiful]] to the point where he would do anything to become a female [[spoiler:including attempting a brain transplant with his [[{{transsexual}} biologically female son]] Tetsuo.]] In his final appearance he's dressed as a woman, and a very attractive one despite [[OlderThanTheyLook being in his forties]], but is very unhinged.
20th Feb '16 3:09:38 AM IndirectActiveTransport
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* 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.

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* Harvey Whippleman as "Harvina" won the WWF Women's Championship, and Santino Marella's Wrestling/SantinoMarella's [[PaperThinDisguise identical twin sister]] "Santina" won the Miss WrestleMania Wrestling/WrestleMania battle royale.royale.
* Kyle Kruze became one in Nova Scotia based Main Stream Wrestling so he could challenge [[Wrestling/SarahStock Sweet Sarah]] to a "[[GimmickMatches bra and panties match]]".
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]]



* Bèbelle 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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* Bèbelle 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]]
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http://tvtropes.org/pmwiki/article_history.php?article=Main.CreepyCrossdresser