History Main / CreepyCrossDresser

* In ''WesternAnimation/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.
--> "Oh well, I suppose it does make me look pretty."

-->'''[[spoiler:Dorkus]]''': You, uh, probably shouldn't tell Heloise about this.\\
'''Jimmy''': Really, I wouldn't know how.

* In ''WesternAnimation/TheSimpsons'', episode "There is Something About Marrying", pro golfer Veronica was going to marry Patty under the false pretense of being a lesbian woman. (It's somewhat unclear, but Veronica doesn't seem to be genuinely UsefulNotes/{{Transgender}} so much as a creepy male golfer who only crossdresses so that he can compete on the womens' tour.)
* HIM, the FlamingDevil from ''WesternAnimation/ThePowerpuffGirls1998'', usually dresses in a fuzzy pink skirt and thigh-high stilleto boots. His voice also tends to shift between falsetto and a deep growl depending on his mood.

* Website/ThatGuyWithTheGlasses:

* ''Series/TheOuterLimits1995'': In "What Will the Neighbors Think?", after he sleeps with a woman, Dom Pardo likes to keep their underwear and wear it himself as he loves the feel of the silk against his skin. He does so with underwear belonging to Shirley Baxter and Delia Pendergast. After gaining telepathic powers, Mona Bailey uses this piece of information to blackmail Dom into letting her join his poker game with Shirley and Delia's respective husbands Vince and Miles.

A {{Crossdress|er}}ing character whose choice of attire is played for weirdness, for creepiness, for {{Squick}}, simply for shock value, or to show that he (and it's virtually [[AlwaysMale 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 exaggerates TertiarySexualCharacteristics without bothering to cover up secondary ([[FullFrontalAssault or primary]]) ones. MakeUpIsEvil is often involved. Frequently, the [[UnfortunateImplications unfortunate implication]] is that crossdressing is, in itself, creepy, but it may simply be one aspect of a character who's ''generally'' creepy.

* In ''LightNovel/TheGardenOfSinners'', Lio Shirazumi starts dressing and styling himself like Shiki and committing murders like this. The fact that he manages to look seriously creepy in a rather silly looking skirt says a lot.

** Narciso Anasui from ''Manga/StoneOcean'' might classify as this depending on who you ask, given his SociopathicHero nature. But he is technically part of the "good guys", so he might be in a different category of [[WholesomeCrossdresser crossdresser]].
** Despite what his name may suggest, [[GenderBlenderName Mrs. Robinson]] from ''Manga/SteelBallRun'' is both a crossdressing man and one of the creepiest [[StarterVillain Starter Villains]] of any Part.
* The ''Franchise/{{Kirby}}'' [[Anime/KirbyRightBackAtYa anime]] has Escargon, a CampGay villain with a not-so-subtle crush on his boss who has crossdressed a few times (usually because said boss wanted him to).

* ''Anime/{{Pokemon}}'' loves crossdressing villains:

[[folder:Films — Animation]]

[[folder:Films — Live-Action]]

* ''Film/AceVenturaPetDetective'' has the villain Lois Einhorn, who is actually disgraced football player Ray Finkle, who had [[DisguisedInDrag stolen the identity]] [[DeadPersonImpersonation of a missing hiker]]. The creepiness is less because of appearance, as it's a FairCop who impresses the men around (to the point that Ace is [[UnsettlingGenderReveal particularly grossed out when he figures out Einhorn is a man]]... as does everyone else, ''including a dolphin'', when he reveals it to a roomful of policemen), but for behavior, as it's a "transition" done for the sole reason of exacting a murderous revenge plot.

* [[https://www.youtube.com/watch?v=TwWQYg7aS5o A fan video]] for Music/MrBungle's ''Pink Cigarette'' revolves around a woman being stalked by a man in a dress and a wig with lipstick smeared all over his face. Adding to this is the fact that there's a recurring fantasy sequence where he's sweeping her off her feet rather than attacking her, and in those shots the same character is dressed in a suit without the makeup or wig.

* ''ComicBook/ThePunisher2001'' had The Russian, an AxCrazy {{cyborg}} HuskyRusskie whose augmentations involved hormone injections that resulted in him growing GagBoobs. He took this in stride and started wearing women's clothing, with ComicBook/SpiderMan calling him "[[ComicBook/ManThing Giant-Sized Ma'am Thing]]".

* Fish Eye from ''Manga/SailorMoon'' has shades of this, though is clearly intended to appeal to the fetish. As the other villains disguise themselves, the HandWave is dressing as a woman is simply a ''modus operandi'' to cover the [[CastSpeciation left over type of victims -- males]] -- as Hawks Eye targeted older women and Tigers Eye targeted younger women. He actually dresses as a male for a specific mission (targeting gay fashion designer Yoshiki Usui), and while exclusively using ''male'' pronouns when in circus attire, will only use ''feminine'' pronouns when disguised. Ironically, his femininity seems to make him [[WomenAreWiser closer to Earth]], and he has the first HeelFaceTurn of the season.

* The Big Cheese from ''Anime/SamuraiPizzaCats''. Strangely, his flirting with male subordinates was mostly left intact.

* [[GenderFlip Tamamo no Mae]] from ''[[VideoGame/{{Onmyoji}} Onmyōji]]'' who often assumes the form of a woman (which is also his [[PowerMakeover Awakened]] appearance) to go around wrecking havoc. This and his [[Creator/RomiPark voice actress]] makes him the victim of a lot of ViewerGenderConfusion.

* ''LightNovel/AscendanceOfABookworm'' has Justus, a SeekerArchetype who has channeled his great hunger for information and willingness to go to great lengths to obtain it into doing spy work. Since he lives in a society in which gender segregation is far from being absent, there are some places he can't go without making use of DisguisedInDrag. If his willingness to do so gets any in-universe comment, it's treated as one of his bigger quirks among the laundry list he has accumulated in the midst prioritizing information gathering over several social norms. One of such comments comes from the protagonist, who switches from not wanting Justus in her orphanage without their shared CloudcuckoolandersMinder to watch him to not wanting him inside it at all when he seriously offers to cross-dress to avoid making the DoesNotLikeMen adult residents of the girl's building uneasy.

* ''Webcomic/{{Unsounded}}'': Ruckmearkha--a giant, monsterous, soul eating [[SnakePeople snake man]]--dresses as an unsettling version of Yerta with a creepy mask for Treenahin. He's not so much trying to look like a person as he's disguising himself as a pymaric for the parade, and his plump belly to immitate Yerta's pregnant one is created by stuffing poor mangled [[spoiler:Roger]], his latest braindead victim, in a bag under his dress.

Sometimes coincides with both TransEqualsGay and DepravedHomosexual, for a lethal combination of stereotypes. May overlap with DisguisedInDrag (or, very rarely, its DistaffCounterpart, SweetPollyOliver) if the character adopts a crossdressing disguise more often than seems strictly necessary and/or enjoys it. Also may overlap with FanDisservice. For the opposite, see WholesomeCrossdresser. See also SissyVillain.

* Chapter 279 of ''Manga/AirGear'' reveals that the villainous loli Shalott who dresses in a frilly dress and wears a hat is [[UnsettlingGenderReveal actually a guy]].

* Doc Fingers in ''VideoGame/Cyberpunk2077'', a perverted MadDoctor who's described as having the fashion sense of "a fourteen-year-old girl stuck in the body of a bum". He's a thin, balding middle-aged man with a pencil mustache wearing a fishnet tank top, pink short-shorts, a belly dancer's sash, make-up and pink FemmeFatalons. What makes him even creepier is that he's infamous for giving his clients (primarily struggling prostitutes) low-quality cybernetics, forcing them to frequently come back for repairs or replacement while accepting "[[SexualExtortion other]]" forms of payment if they can't afford it. Despite all of this, he can provide some of the best cyberware in the game to players that can afford it ([[HateSink and resist the urge to beat him to death]]).

* Dark Sun Gwyndolin from ''VideoGame/DarkSouls'' was a male moon god born to a family of sun gods. As the moon is associated with femininity he was raised as a daughter and wears feminine clothing which makes it looks like he has breasts. The 'creepy' part comes from the fact he lurks in a hidden tomb and has ''dozens of snakes for legs.'' His personality is otherwise fairly normal.

* ''Anime/FullmetalAlchemist'':

!!!'''Series:'''