History Main / CreepyCrossDresser

* Canadian Col. Russell Williams, who is as of October 2010 being sentenced for multiple murders, sexual assaults, breaking and entering, and so on, took thousands of photos documenting his crimes. The ones the papers put on their front pages to show what a horrific monster he was? That'd be the ones of him wearing women's underwear, because any man who ever does ''that'' [[UnfortunateImplications is obviously a disgusting pervert]].
** 'Ahem'. That happened to be [[SickAndWrong''little girl's underwear'']]. Taken with [[MoralEventHorizon all the other shit]] he pulled, he was [[CompleteMonster ''beyond'']] a "disgusting pervert.

** Earl Kanon Maldini, the aide to Prince Schneizel. In the series, he is not shown as a crossdresser (but he ''is'' [[AlwaysCamp feminine looking enough]] and once jokes about [[SubordinateExcuse aiding]] [[HoYay Schneizel]] [[IfYouKnowWhatIMean in "his private affairs"]] as well), but [[AllThereInTheManual the Code Geass novels]] say he is.
** Kanon [[AllThereInTheManual is a crossdresser.]] He [[TruthInTelevision was persecuted for it]] until he met Schneizel.
** [[MagnificentBastard Lelouch]] does this at least twice in the picture dramas. In one of them, the Student Council has a crossdressing festival so everyone crossdresses (and Suzaku... mentions having done it a few times before?).

* GhostInTheShell:StandAloneComplex has a special case in which [[spoiler: Pazus]] ex-girlfriend wants to kill him and take both his cybernetic body and his identity.
** [[spoiler: Hard to say, but she might very well have succeeded.]]
* [[spoiler: [[CreepyChild Sakurako]]]] from SakuraGari [[spoiler: is actually Souma's brother, named Youya. He stole his mother's name and dressed in her clothing after she died. Soon after his gender was discovered, he committed suicide.]]

* Creed, who is actually the BigBad in ''BlackCat'', fits this pretty well. Although he doesn't out-and-out crossdress, he certainly dresses in very flamboyant clothing, has an annoying evil laugh, and is extremely narcissistic (Rinslet even refers to him as "that narcissist"). AND it's made very obvious that he has a [[StalkerWithACrush huge and obsessive crush]] on Train.

* Casey(WillKeenan), the killer in ''TerrorFirmer''.

A [[{{Crossdresser}} Crossdressing]] character whose dressing is played for weirdness, for creepiness, for {{Squick}}, simply for shock value, or to show that he (and it's virtually always "he") is evil or deranged. While the look of the WholesomeCrossdresser tends to gloss over the dissonance between genders, this trope often calls attention to it. Often, this crossdresser [[{{FetishFuelStationAttendant}} fetishistically ]]exaggerates TertiarySexualCharacteristics without bothering to cover up secondary ([[{{FullFrontalAssault}} or primary]]) ones. Frequently, the [[UnfortunateImplications implication]] is that crossdressing is, in itself, creepy, but it may simply be one aspect of a character who's ''generally'' creepy.

** Made even worse in an omake where he and his apprentice, Kabuto, show up... wearing SailorFuku. [[BrainBleach UGAH!]]

* Suzu in ''PeacemakerKurogane'' dresses in a more feminine manner after becoming gay and insane. He wears nail polish, makeup, revealing clothes, and sometimes wears a long, black [[FurAndLoathing fur robe]] (without wearing anything else inside).

** Supposedly, Jakotsu was originally supposed to be a woman, but the author changed it because she didn't like the idea of the characters killing a human woman, undead or not. Regardless of the gender-switch, Jakotsu is also the most psychotic and murderous of the Band of Seven, with quirks that include sadism and a heavily implied tendency to torture his "lovers" to death.

* Herman Goering's transvestite habits were brought up in A.E. Hotchner's novel ''The Man Who Lived at the Ritz''.

* RealLife transvestite head of the Nazi ''Luftwaffe'' Herman Goering was depicted in a 1988 TV Movie, ''The Man Who Lived at the Ritz'', based on A.E. Hotchner's novel.

* Herman Goering was depicted as a transvestite in A.E. Hotchner's novel ''The Man Who Lived at the Ritz''.

* RealLife head of the Nazi ''Luftwaffe'' Herman Goering was depicted as a transvestite in a 1988 TV Movie, ''The Man Who Lived at the Ritz'', based on A.E. Hotchner's novel.

* Haku from ''{{Naruto}}''. When Naruto actually [[DroppedABridgetOnHim finds out]], he yells "WHAT? No way! He's prettier than Sakura!" Though he is actually an AffablyEvil BattleButler.
** Orochimaru, also from ''{{Naruto}}'', who is actually a man [[BodySurf in a woman's body]] (by the start of the series) ShapeShifting as an effeminate male.
** Haku is really more of an AntiVillain. He's a good person who does bad things out of obligation to Zabuza, whom he owes his life to. Still, he's done enough wrong to qualify for this trope.
** Zabuza even states that having to fight Naruto and company broke his (Haku's) heart. He was ultimately a kind person who had a [[{{Understatement}} horrific childhood]] and was living his life only for Zabuza's sake, seeing as Zabuza was the first and only one who saw his [[CursedWithAwesome genetic defect]] as a good thing.

** Haku is really more of an AntiVillain. He's a good person who does bad things out of obligation to Zabuza, whom he oews his life to. Still, he's done enough wrong to qualify for this trope.

** Team Rocket, often ([[OnceAnEpisode Oooh, I think I know that episode.]]) Subverted once when Jessie crossdressed as a male (complete with mustache), while James crossdressed as a female at the same time. No reason was given why they couldn't just disguise themselves as their own gender.

May overlap with DisguisedInDrag (or, very rarely, its DistaffCounterpart, SweetPollyOliver) when the character adopts a crossdressing disguise more often than seems strictly necessary and/or ''enjoys'' it. For the opposite, see WholesomeCrossdresser.

For the opposite, see WholesomeCrossdresser. May overlap with DisguisedInDrag (or, very rarely, its DistaffCounterpart, SweetPollyOliver) when the character adopts a crossdressing disguise more often than seems strictly necessary and/or ''enjoys'' it.

This trope can be played in a number of ways, but a few common traits tend to turn up in Japanese works: a combination of a gaudy outfit, a NoblewomansLaugh and absolute narcissism. He also often has a crush on the BigBad, TheDragon, or in more humorous works, the ChasteHero.

A [[{{Crossdresser}} Crossdressing]] character whose dressing is played for weirdness, for creepiness, for {{Squick}}, simply for shock value, or to show that he (and it's virtually always "he") is evil or deranged. While the look of the WholesomeCrossdresser tends to gloss over the dissonance between genders, this trope often calls attention to it. Often, this crossdresser [[{{FetishFuelStationAttendant}} fetishistically ]]exaggerates TertiarySexualCharacteristics without bothering to cover up secondary ([[{{FullFrontalAssault}} or primary]]) ones. Frequently, the [[UnfortunateImplications implication]] is that crossdressing is, in itself, creepy, but it may simply be one aspect of a character who's creepy for multiple reasons.

For the opposite, see WholesomeCrossdresser.

* "I have the biggest balls in this whole city. That's right, I said it." Play as a Latin female in ''SaintsRow'' and she'll hint at this.

* Earl Kanon Maldini, the aide to Prince Schneizel in ''CodeGeass''. In the series, he is not shown as a crossdresser (but he ''is'' [[AlwaysCamp feminine looking enough]] and once jokes about [[SubordinateExcuse aiding]] [[HoYay Schneizel]] [[IfYouKnowWhatIMean in "his private affairs"]] as well), but [[AllThereInTheManual the Code Geass novels]] say he is.
** Then again, IIRC Kanon is mentioned to have been fired from several jobs despite his great competence... purely ''because'' of his crossdressing. Schneizel is the only boss of his' who doesn't mind it, so!

** [[spoiler: Hard to say, but she might very well have succeded.]]

* [[MetalHeroes Uchuu Keiji Shaider]]'s main villain's grandson is the crossdressing Shinkan Poe, who, in a [[NightmareFuel scary series of events]], is revealed to be [[spoiler: a demon who preserves his "beauty" by drinking a potion made of young girls' beauty every millenia or so]].

* Mr. 2 Bon Clay of Baroque Works, from ''OnePiece''. He's the only Baroque Works officer without a female partner, since he counts as both the man and the woman.
** [[spoiler:[[DefeatMeansFriendship Though after losing]], he pulls a HeelFaceTurn, like many ''One Piece'' villains, transforming into a WholesomeCrossdresser.]]

* Sakko from SuperRobotMonkeyTeamHyperforceGo

* In TheFairlyOddparents, Timmy managed to humiliate Crocker on a global scale and get him arrested for developing a supposed computer virus by uploading a video file of himself modeling one of his mother's dresses.

A [[{{Crossdresser}} Crossdressing]] character whose dressing is played for weirdness, for creepiness, for {{Squick}} value, or to show that he (and it's virtually always "he") is evil or deranged. Frequently, the [[UnfortunateImplications implication]] is that crossdressing is, in itself, creepy, but it may simply be one aspect of a character who's creepy for multiple reasons.

* Dr. Frank N. Furter from ''[[TheRockyHorrorPictureShow The Rocky Horror Show]]''. Also a DepravedBisexual.