[[quoteright:350:[[Film/TheDarkKnight http://static.tvtropes.org/pmwiki/pub/images/nolan5.png]]]]
[[caption-width-right:350:[[JustForFun/{{Hello}} Hi...]]]]

->'''Bugs Bunny:''' Usually, ''([[HyperspaceWardrobe spins to change into female garb]], speaking in a feminine voice)'' I play the female love interest.
->'''Kate Houghton:''' About the crossdressing thing: In the past, funny. Today, disturbing.
-->-- ''Film/LooneyTunesBackInAction''

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 played UpToEleven. 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.

Japanese works tend to play up a few common traits for this character type: 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.

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.



[[folder:Anime & Manga]]
* Examples from ''Manga/FistOfTheNorthStar'':
** Yuda represents the essence of this trope, particularly as played in anime. Outrageous outfit? Check. Annoying laugh? Check. Insanely self-absorbed and narcissistic? To ''eleven''. Also obviously, albeit not explicitly, a DepravedBisexual.
** Dekai Babaa is a giant thug disguised as an old woman and tried to give poisoned water to the heroes, but his old lady facade wasn't convincing enough for them.
* In ''Anime/AkazukinChaCha'', Doris is the twin brother of Dorothy who is in love with their childhood friend Seravy, who has BelligerentSexualTension with Dorothy, ever since she had a makeover which Seravy hates (she changed her natural golden curls to a straight red-pink hair). In an effort to win Seravy's affections, he himself had a makeover to ''look exactly like his sister's original appearance.'' Naturally, this only {{Squick}}s Seravy out to the point he is usually very violent to Doris (and ''only to Doris''.)
* ''Manga/HaouAiren'': Huo Long. His heart is in the right place, but he ''is'' a Triad member.
* ''Manga/OnePiece'' examples:
** Mr. 2 Bon Clay of Baroque Works, the only Baroque Works officer without a female partner, since he counts as both the man and the woman. His alias reflects this, being a combination of a number (traditional for male officers) and and a reference to a holiday (traditional for female officers). [[spoiler:[[DefeatMeansFriendship Though after losing]], he pulls a HeelFaceTurn, like many ''One Piece'' villains, transforming into a WholesomeCrossdresser.]]
** Taken to absurd levels with Emporio Ivankov, the "[[DragQueen queen]]" of Kamabakka Kingdom. His design was modeled on no less than Dr. Frank N. Furter himself. When he was arrested and locked in Impel Down, he founded a Prisoner's Paradise between the prison's two harshest floors where everyone dressed in fishnet stockings and switched freely between genders thanks to Iva's hormone controlling "Horu-Horu" Fruit.
** And yet despite his absurd level of creepiness, he can still be considered one of the top good guys of the entire ''One Piece'' world, being [[spoiler:a commander of the [[LaResistance World Revolution Army]], just about the ''only'' faction who opposes the corrupt World Government for presumably altruistic reasons (for most pirate crews it's more a case of EvilVersusEvil)]]
* Kamatari of ''Manga/RurouniKenshin'', though he's portrayed fairly sympathetically and is driven by an unrequited love for Shishio. Otowa, on the other hand, is just a PsychoForHire.
* Jakotsu from ''Manga/InuYasha'' has a crush on Inuyasha (and flirts with Miroku and Sesshomaru), but later [[HiddenDepths is shown in a more sympathetic way]] through his genuine friendship with Bankotsu. 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 tendency to torture his "lovers" to death. For example, he says Inuyasha's ears are [[ALoveToDismember so cute he wants to cut them off.]]
* Suzu in ''Manga/PeacemakerKurogane'' dresses in a more feminine manner after becoming [[DepravedHomosexual gay and]] [[UnfortunateImplications insane]]. He wears nail polish, makeup, revealing clothes, and sometimes wears a long, black [[FurAndLoathing fur robe]] (without wearing anything else underneath).
* ''Anime/FullmetalAlchemist'':
** 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 [[Manga/FullmetalAlchemist the manga]] has no gender (or, according to [[WordofGod Word of God]], no one knows Envy's true gender Ė 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 first appeared dressing as a woman when out delivering meat from his butcher shop. He kidnapped Winry and [[WouldHurtAChild almost murdered]] both her and Edward.
* 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 a gay fashion designer), 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.
** Also Zoisite, though played a bit straighter (no pun intended) than the openly camp Fish Eye. Guilty of feminine appearance, romantic relationship with a male, shrill laugh, and sakura petals ''everywhere''. Fits this trope because he actually crossdresses as the title heroine in order to lure Tuxedo Mask out of hiding. Though the crossdressing was Kunzite's idea, not his.
** Zoisite and Nephrite both crossdress to disguise themselves in the manga. Also, it is not Fish Eye but Hawks Eye who crossdresses in the manga.
** Also of note in regards to Fish Eye, in one episode he dresses up as a female ballerina with clearly visible breasts and cleavage. Regardless if it was magic or not, he showed he was ''really'' committed to pulling off a good disguise.
* Elendira the Crimson Nail from ''Manga/{{Trigun}} Maximum'' (the later volumes of the manga), although he or she is most likely a {{transgender}} woman.
** Given the body-mod capabilities of Gunsmoke science demonstrated in the series, she could be, but could also still be male. Either way, she's scary as hell, one-upped Legato by some way, but was sadly too freaky (as much for the 'fighting style based on graphic impalement with giant red hardware from [[HammerSpace nowhere]]' bit as for being transgender) to get into the anime.
*** Notable for the fact that, unlike Kamatari above, although she's competing for the affection of a man who will never look at her she's easily the most sane ''and'' the most physically powerful force he can mobilize, until he [[spoiler: goes [[OneWingedAngel Million Winged Angel]].]] (Meanwhile [[TheWoobie Legato's]] 'eat steak with no hands' and 'float around in sarcophagus of doom' lines have inspired mutinies out of sheer embarrassment from his subordinates.
*** [[spoiler:Incredibly drawn-out death sequence was solid horror.]] Can we get Freudian about those humongous nails [[DoesThisRemindYouOfAnything ramming through bodies]], please?
* The Big Cheese from ''Anime/SamuraiPizzaCats''. Strangely, his flirting with male subordinates was mostly left intact.
* Lady Bat from ''Manga/MermaidMelodyPichiPichiPitch''
* [=McCoy=] from the anime ''Anime/BakuenCampusGuardress'' is a semi-subversion of this trope. He has the laugh, the mascara and the leather dominatrix outfit, he brags about how beautiful he is.... [[{{Gonk}} and he is built like a linebacker]].
* Orochimaru of ''Manga/{{Naruto}}'', who is actually a man [[BodySurf in a woman's body]] (at the start of the series) ShapeShifting as an effeminate male. Just to make matters creepier, he first shows up wearing a woman's face as a disguise, after ''tearing it off''.
** Made even worse in an omake where he and his apprentice, Kabuto, show up... [[FanDisservice wearing]] SailorFuku. [[BrainBleach UGAH!]]
** Gai on occasions in ''Manga/RockLeesSpringtimeOfYouth''.
* ''Manga/FlameOfRecca'''s Kurenai may be effeminate, but the real version of the trope doesn't appear until very late in the manga when the clone Aoi poses as a female student. Recca seems nonplussed considering the much stranger people he's met at this point, except in being completely confused by the [[HeelFaceTurn reformed]] Aoi trying to explain his complicated backstory.
* ''Manga/{{Monster}}'' offers a particularly creepy example in which this trope is '''not''' played for laughs. [[spoiler:Johan impersonates his twin sister, Anna, in a flawless fashion that is quite disturbing. He still manages to sound threatening while wearing a dress, which says a ''lot'' about how ultimately creepy he can be. Interestingly, the creep factor doesn't come so much from the gender implications so much as how much it represents his concept of himself and Anna as the same person.]]
* ''Manga/{{Bleach}}'':
** Charlotte Chuhlhourne is a flamboyant MagicalGirl parody. His normal attire may involve trousers, but he wears a tight tank top with plunging, frilly neckline and bared midriff, and his trousers expose the tops of his thighs on each side as well as revealing a little too much of his [[FanDisservice pelvic area]]. His hair is very long and painstakingly curled and styled and he wears long, false eyelashes. In his Resureccion form, called ''Reina de Rosas'', he transforms into a frilly, bikini-style tutu costume that is designed with the petals of a [[FlowerMotif rose]] in mind. He's extremely proud of his [[MachoCamp muscular strength]] and his costumes are designed to show off his body as much as possible.
** Giselle is accused of being a man by Yumichika but neither confirms nor denies the accusation. While she actually dresses in a quite wholesome-looking fashion, the more that's revealed about her, the less wholesome she appears. [[spoiler:Yumichika claims she reeks of semen, and a [[TheUndead resurrected]] Charlotte also identifies her as "[[DragQueen resembling]]" him after sniffing her. Giselle creates zombies by infecting shinigami with her blood and even kills her Quincy friend Bambietta to turn her into a zombie. She drools when excited and the thought of using her blood on others seems to turn her on.]]
* ''Anime/{{Pokemon}}'' loves crossdressing villains:
** 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, where James has a pair of inflatable breasts that led to the episode being banned. Amusingly, no reason was ever given why they couldn't just disguise themselves as their own gender.
** Harley is also a great, albeit much less permanent, example, but technically he only crossdresses once.
* ''Manga/JoJosBizarreAdventure''
** [[NamesToRunAwayFromReallyFast Diavolo]], the BigBad in Part 5 straddles dangerously close to this with both of his personalities.
** Annasui 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]].
** In Part 2, TheHero Joseph dressed as a woman in order to fool guards into getting past. The result was... [[{{Gonk}} not convincing]].
* ''Anime/CodeGeass'' examples:
** 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]] in "his private affairs" as well), but [[AllThereInTheManual the Code Geass novels]] not only say he is, but that he [[TruthInTelevision was persecuted for it]] until he met Schneizel and was hired as his assistant.
** [[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?).
* Tsubasa Kurenai from ''Manga/RanmaOneHalf''. A straight guy who dresses up like a schoolgirl and relentlessly stalks former schoolmate Ukyo Kuonji (a straight girl who spent most of her life [[{{Bifauxnen}} dressing up like a guy]]) while disguised as various inanimate objects. Tsubasa is assumed to be a lesbian at first because he's ''very'' passable and is only interested in women. Ranma tries dating Tsubasa while in male form to set "her" straight, only to find that Tsubasa [[UnsettlingGenderReveal is a boy]].
* Mariya from ''Manga/MariaHolic'' does a very convincing job as a girl. Since this is an all girls' school, no surprise that he gets Kanako falling for him the moment they meet. He's also incredibly sadistic.
* One early example of this trope would be Rock, from the various manga by Creator/OsamuTezuka. Who, in his more villainous incarnations, would often disguise himself as a woman.
* Yuuji Fukunaga from ''Manga/LiarGame'' starts off as this, but slowly pulls a HeelFaceTurn and becomes one of the main supporting characters while still making a better looking girl than most of the female cast combined.
* 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).
* Fumiya Ninomiya from ''Manga/WanderingSon'' crossdresses just to impress Saori Chiba. While not an outright "villain", he is portrayed as a bit of a slimeball when compared to the actual transgender people.
* ''Anime/GhostInTheShellStandAloneComplex'' has a special case in which [[spoiler: Pazu's]] PsychoExGirlfriend wants to kill him and take both his cybernetic body and his identity. [[spoiler: Fortunately, the real Pazu won. There are just enough clues at the end of the fight to prove it.]]
* [[spoiler:[[CreepyChild Sakurako]]]] from ''Manga/SakuraGari'' [[spoiler:is actually Souma's brother, named Youya. He stole his mother's name and dressed in her clothing after she died, having been traumatised after witnessing said mom's murder at the hands of Souma and Katsuragi. Soon after his gender was discovered by Masataka, he tried to kill both him and Souma, then had a heartbreaking VillainousBreakdown and [[DrivenToSuicide committed suicide]].]]
* [[EvilTwin Rosiel]] from ''Manga/AngelSanctuary'' often [[IncrediblyLamePun skirts]] the line with his... ''[[FashionVictimVillain unusual]]'' [[FashionVictimVillain outfits]]. AntiVillain [[{{Bifauxnen}} Belial]] also counts.
** PlayedForDrama with [[spoiler:[[SamusIsAGirl Sevothtarte]]]].
* Chapter 279 of ''Manga/AirGear'' reveals that the villainous loli Shalott who dresses in a frilly dress and wears a NiceHat is [[UnsettlingGenderReveal actually a guy]].
* [[CreepyTwins Hansel and Gretel]] of ''Manga/BlackLagoon'' are very fond of swapping clothes (and, more disturbingly, ''personalities'') with each other. Which one's which gender, though, is [[AmbiguousGender anyone's guess]].
* ''Manga/BlackButler'': In episode five of the second season, [[CuteAndPsycho Alois]] [[CreepyChild Trancy]] dresses up as a maid to lure Ciel into his bedroom so he can flirt with him and take his eyepatch. It's also shown that he has a few dresses in his wardrobe.
* "Miss Aki," an unattractive example from ''Anime/MagicalShoppingArcadeAbenobashi''
* Count D in ''Manga/PetshopOfHorrors'' is good friends with a group of drag queens and transvestites, and his peacocks also appear this way in their 'human' forms.
* The bad guy in ''Anime/LupinIIIThePursuitOfHarimaosTreasure'' was [[ThoseWackyNazis Herr Maphrodite]], who doubles as a SissyVillain and EffeminateMisogynisticGuy, as well. The clothing and behavior during the villain scenes made him creepy long before we find out who he really is.
* Michio Yuki of manga series, ''Manga/{{MW}}'', cross-dresses as his female victims after killing them.
* In ''Manga/MyBrideIsAMermaid'', Both Sun and Lunar's fathers try to get to know their daughters a little better by exploring some research into teenage life (I.E: they explored a goofy DatingSim). The end result completely horrifies ''EVERYONE'' else, especially the two girls. Seeing the anime equivalent of the Franchise/{{Terminator}} wearing a sailor fuku is not a pretty sight. Funny, but not pretty.
* Baikinman from ''Franchise/{{Anpanman}}'' will commonly disguise himself as characters to either get the character he's disguised at in trouble, or to get free food out of people. Most of the time, he'll end up disguising himself as some of the female characters...even if Dokinchan is with him. When he disguises as a female character, Dokinchan will either crossdress as a male character that works with the female character, or even sometimes make up a male counterpart to the existing female character.
* ''Anime/AnoHanaTheFlowerWeSawThatDay'': A more tragic example. After the death of his childhood love, Menma, Yukiatsu takes to dressing up as her and running around their childhood hangout at night. This is his way of coping with his loss.
* Happens, accidentally, to Sora in ''Manga/KingdomHeartsII'', when the fairies put him in a ball gown (complete with tiara) while designing a new outfit for him. It's clear from that scene that he hates cross-dressing.
* Kaito from ''Himegoto - Juukyuusai No Seifuku'' comes off as this at first. He is a man who enjoys dressing up as the woman he has a crush on, a JerkAss who toys with women's emotions, pretended he was gonna rape Yuki, and generally acts manipulative and sly. However, the further the manga goes the more it becomes obvious that Kaito is more likely {{Transgender}} than just a villainous crossdresser. His obsession with Mikako is creepy, however, a lot of things he does happen out of fear for not being accepted the way he is. The time he spends with Yuki as his girl persona he is a genuinely caring and nice person, albeit somewhat pushy. And the women he goes out/sleeps with to get money so he can afford his other life as a girl are middle-aged women who sleep with a 19-year-old to prove to themselves they're still desirable. He is sly and manipulative, but actually pales in comparison to his crush Mikako.
* Osamu from ''Manga/BokuraNoHentai'' has shades of this. He's portrayed as less emotionally stable than the other crossdressers.
* Izumi from ''Boku to Boku'' isn't too villainous but he's portrayed as a perverted, more mean spirited foil to the WholesomeCrossdresser Jun.
* [[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 [[{{transgender}} 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.
* In ''Manga/Brave10'', one of the [[VillainOfTheWeek villains of the week]] Ishikawa Goemon turns out to be one. Since his whole family was targeted to be exterminated, he had to disguise himself as a girl. TokenEvilTeammate Kamanosuke has also used this to [[WoundedGazelleGambit trick people]] back when he was a bandit.
* Even ''Franchise/PrettyCure'' got in on this, as [[Anime/HappinessChargePrettyCure Phantom, the Pretty Cure Hunter,]] went into battle as Cure Un-Lovely, a Cure Lovely lookalike dressed in [[RedAndBlackAndEvilAllOver red and black]], in one episode.
* In ''LightNovel/KaraNoKyoukai'' 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''.

[[folder:Comic Books]]
* The Purple Marauder, transvestite women-hating archnemesis of the AntiHero Lusiphur, the elvish protagonist of the series ''Poison Elves'' (originally titled "I, Lusiphur") by late artist/writer Drew Hayes (1969-2007). The Purple Marauder (a human) is a foppish Zorro-like vigilante swordsman who terrorizes the world of Amrahly'nn with his rapier and mustache-twirling villainy but mainly with the sight of his hairy fishnet-clad legs. He dresses, as the name insinuates, all in purple from head to toe: large purple hat, purple women's dress, purple boots. His sworn mission: To convert men from the ways of lust and women.
* While he's technically more of a mercenary with a small modicum of heart and it was only the once, when {{Deadpool}} spent a brief time with the X-men he insisted on wearing one of their costumes. Specifically, Marvel Girl's. For unknown reasons he also retained the underwear from the costume underneath his suit even when he went back to his black-and-red tights.
* In Creator/GrantMorrison's ''Comicbook/ArkhamAsylumASeriousHouseOnSeriousEarth'', the Joker was originally going to be sporting a costume with Madonna's signature cone-shaped bra and stilletto boots, simply because [[ForTheEvulz he knew it would make Batman highly uncomfortable]].
* In ''Comicbook/AmericanFlagg'', [[spoiler:Ivor Overholt]], who makes himself into a doppelganger for the presumed-dead [[spoiler:Peg Krieger]] in order to seduce and blackmail a character who was obsessed with her. Possibly a borderline example of EasySexChange as well, though the character still had his original genitalia and still appeared as a man in public.
* GoldenAge ComicBook/WonderWoman foe Blue Snowman was a rare female version of this, being a woman who dressed up in a male snowman outfit to commit crimes.

[[folder:Comic Strips]]
* Sanjak from ''ComicStrip/TerryAndThePirates'' is a rare female version.

[[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:Films -- Animation]]
* Snatcher performs as Madame Frou Frou to spread fear of ''WesternAnimation/TheBoxtrolls''.

[[folder:Films -- Live-Action]]
* Dr. Frank N. Furter from ''Film/TheRockyHorrorPictureShow''. Also a DepravedBisexual, [[EvilIsSexy not that anyone's complaining.]]
* Buffalo Bill from ''Film/TheSilenceOfTheLambs''. He seems to be an erotic crossdresser who's expressed interest in sex-reassignment surgery. Dr. Lecter and Clarice agree that he's not really transgender.
* ''Film/AceVenturaPetDetective'': The 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:''' 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.
* 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". 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.]]
* Even Film/JamesBond's nemesis Blofeld undertook a spot of cross-dressing (although it was technically a desperate disguise) in the film adaptation of ''Film/DiamondsAreForever''. Also, ''Film/{{Thunderball}}'' has an old enemy of Bond disguised as his own "widow".
** Charles Gray was a fitting choice as the criminologist in ''Film/TheRockyHorrorPictureShow''.
%%* Creator/MichaelCaine in ''Film/DressedToKill''.
* In ''Film/TheDarkKnight'', The Joker disguises himself as a nurse in one scene to get to Harvey in the hospital. Instead of wearing unisex scrubs or just dressing as a male nurse, he goes drag, complete with a wig. It manages to be funny and creepy at the same time. It was likewise intentionally [[InvokedTrope invoked]], seeing as he'd kept his Joker facepaint and green hair color (and displayed in an earlier scene that he was willing to go without them when making a sincere effort to disguise himself).
* ''Freebie and the Bean'', a buddy cop film from the 70's, features a beautiful blond crossdressing antagonist played by Christopher Morley.
* After the climax of ''Film/AlvinAndTheChipmunks: The Squeakquel'', [[CorruptCorporateExecutive Ian Hawke]] tries to stand in for the Chipettes after he lost them, [[PaperThinDisguise failing spectacularly]].
* [[spoiler: Casey (Will Keenan), the killer]] in ''Film/TerrorFirmer''.
* Leatherface is a crossdresser in ''Film/TexasChainsawMassacreTheNextGeneration.'' The character was [[VeryLooselyBasedOnATrueStory loosely based on]] real-life killer Ed Gein (listed below) in the first place anyway, so it makes at least some kind of sense, unlike the rest of the movie.
* Norman Bates from ''Film/{{Psycho}}.''
* Both Frank Booth and Ben, two villains from ''Film/BlueVelvet'', deserve some mention here as they both wear feminine makeup at some point in the movie.
* In Film/CaptainBerlin Doctor Sinds mutant is wearing high-heeled shoes
* In ''Film/DeathWishVTheFaceOfDeath'' one of the villains is Fredrick "Freddie Flakes" Garrity ([[SuspiciouslySpecificDenial not at all played by Sid the coroner from]] ''Series/{{CSINY}}''), a high-priced mob assassin (nicknamed because of his frequent dandruff) who not only crossdresses during one of his schemes, but later, when hanging out with his girlfriend, comments her shoes, saying he can't wait to see how they fit. (He also has what is quite possibly the stupidest death of the series, immolated by an exploding soccer ball).
* Gene Simmons's character in ''Never Too Young To Die''.
* ''Film/PiratesOfTheCaribbeanTheCurseOfTheBlackPearl'' sees [[ThoseTwoBadGuys Pintel and Ragetti]] wearing pretty dresses, rowing a boat around the Isla de Muerta to distract the Navy. Ragetti really gets into it, even flirtatiously calling out to some of the confused Navy men ([[FunnyBackgroundEvent some of whom react favorably]]). Pintel is decidedly unhappy.
* Belle in ''Film/FrightNightPart2''. Paired with some rollerskates, he's (she's) definitely OurVampiresAreDifferent.
* {{Deconstructed}} and PlayedForLaughs in ''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'': Detective Smecker (Willem Dafoe) gets a little too into character when dressing drag to infiltrate a mob manor. So do the Mook guards.
* Bob, one of Holli Would's Goons from ''Film/CoolWorld''.
* Zack from the 1988 SlasherMovie ''Film/HideAndGoShriek''.
* Dark from 2002's ''Film/HuntingHumans''. As Website/SomethingAwful put it:
--> "Despite his stupid name, I have to admit that Dark can be a pretty interesting character. Until this point in the movie we never actually see him. When he walks onscreen, however, he steals the show, mostly because he is wearing women's clothing. Without explanation. When you see a cross-dressing serial killer in a movie, he is usually wearing makeup in a dress. Something that says "hey, I am a psycho and I wear clothes that obviously belong to a woman." This is not the case with Dark. Instead of a skirt or something, he wears a pink tube-top and woman's executive jacket with padded shoulders. And, again, this is never explained. It is almost as if the movie goes out of its way to ignore this fact, like the only person who would take the role was some cross-dresser at the bus stop and they're trying to downplay the fact."
* Marion Penrose in ''Unhinged'', due to his mother being an insane misandrist.
* The villain of the Hong Kong slasher film ''He Lives By Night'' is a crossdressing serial killer who prowls the streets at night, brutalizing women before strangling them with white stockings.
* Harry Russo from ''Schizophreniac: The Whore Mangler'' and its sequels, apparently the result of his horribly abusive parents wanting a girl.
* While committing murders, [[spoiler:Leonard Marliston]] from ''Film/CherryFalls'' dresses like his mother.
* 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.
* Played distressingly straight in the otherwise comic [[TheSixties 60s]] caper flick ''Caprice'', in which itís revealed that [[spoiler:villainous Stuart Clancy got into the fashion industry so he could wear womenís clothes.]]
* Loco in ''Film/TheGreatSilence'' is a downplayed example who is not PlayedForLaughs. As noted in the original Italian version, he "wears a priest's hat and a woman's scarf".
* [[spoiler: Angela]] turns out to be one in the infamous TwistEnding of the SlasherMovie ''Film/SleepawayCamp''. To be fair though, [[spoiler: she got forced onto Angela/Peter by a demented aunt.]]
* ''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.
* ''Film/TheBorrower'': Scully escapes from the hospital by assaulting and knocking out the female cop who was guarding him. He ties her up and rapes her before he steals her clothes to walk out of the hospital. He even puts on her underwear and lipstick.
* In ''Film/ThirtyOne'', Death-Head wears a tutu.

* One [[UrbanLegends Urban Legend]] features a serial killer disguised as an old woman who [[WoundedGazelleGambit asks passerby to help "her"]].

* ''"Why Grandma, what big eyes you've got!"'' The Big Bad Wolf from ''Literature/LittleRedRidingHood'' is one of the [[OlderThanFeudalism oldest ones in the book]], dressing up as the title heroine's grandmother.
* Norman Bates from ''Film/{{Psycho}}''.
** Norman doesn't really fit the stereotype given in the trope description-- his cross-dressing is to give his other personality a more convincing appearance.
* In the ''Film/{{Redwall}}'' series, Emperor Ublaz Mad Eyes is a possibly-not-intentional-on-the-author's-part borderline example. The silk robes, painted nails and perfume he is mentioned as having in his first appearance are par for the course for an evil exotic emperor, but the entire book revolves around him attempting to steal a famous set of six large pink pearls to put in his crown. He goes so far as to slaughter entire tribes to get the things. He also stops in the middle of his angry MirrorMonologue to debate what he's going to wear for the victory parade; ''"If I had the Tears of all Oceans now, they would be set in my crown, all six of them, wondrous rose-colored pearls! I would don my green silk mantle, or maybe the black one with gold trim..."''
* An odd little novel called ''Pest Control'' by Bill Fitzhugh featured, among other things, a diminutive hitman who likes to dress up as a little girl to do his hits. He also bangs a repressed middle-aged mom who has a thing for midgets and circus peanuts.
* "Adult comics" vendor Sid Sleaze in ''Film/WhoCensoredRogerRabbit?''
* Antiheroic example in ''Literature/{{Discworld}}'''s Nobby, who picked up the habit in Foreignland and has gotten to the point where he asks:
-->Nobby: Do I look good in taffeta?
-->Angua: Erm, yes. Lovely.
-->Nobby: Really? You don't think it makes me look too fat?
* Herman Goering was depicted as a transvestite in A.E. Hotchner's novel ''The Man Who Lived at the Ritz''.
* 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.
* ''{{Literature/I Claudius}}'' features a scene where [[TheCaligula Caligula]] (see below under real life) summons the title character and two other men out to his palace unexpectedly, scaring all three shitless because they expect to be executed, only to shock them when he prances out in full drag and does a performance for them. Also mentions the real life incidents where he dressed as Venus.
* In ''Literature/{{Parrotfish}}'', some football players dress up in drag at the start of a game. It's supposed to be funny and is supposedly a long-standing tradition, however Kita finds it an offensive TakeThat against Grady (who is a {{trans|gender}} boy).

[[folder:Live-Action TV]]
* Borderline-ish example: the second season of ''Series/{{Skins}}'' features a [[StalkerWithACrush character]] who, while still visibly female, binds her chest and dresses in boyish clothes with hopes of making herself more attractive to the object of her romantic obsession, [[FagHag who happens to be gay]]. It doesn't work.
* Alonzo Torquemada of HBO's ''Series/{{OZ}}'' is a tall, strapping Hispanic crossdresser with one glass eye and a penchant for hallucinogens. While not quite as evil as his namesake, Torquemada isn't above slipping his enemies poisoned dope, or seducing Miguel Alvarez.
* When Luke and Laura on ''Series/GeneralHospital'' went on the run in 1980, they eventually encountered Sally, a hitman who wore a dress.
* The episode "Machismo" of ''Series/CriminalMinds'' was RippedFromTheHeadlines about Mataviejitas, "The Old Lady Killer." It featured a man who dressed as a woman to gain entrance into old elderly women's apartments to kill them. The actual case is a subversion. Authorities believed the killer was a man dressing as a woman; in fact, she was just a woman. It's worth pointing out that the show lampshades and (perhaps?) subverts the trope, explicitly stating that their villain is ''not'' a crossdresser: dressing as a woman is not a lifestyle for him, but a tactic.
** It may have actually been more than a tactic. Before he became a serial killer, he was a serial rapist, and even then he wore dresses and the like, despite having no apparent reason to (he didn't use a ruse then, just blitzed the victims, who never really saw him, since he came up from behind and blindfolded them).
** The [=UnSub=] in "Limelight" is a crossdresser, wearing his victim's clothes as a means of reliving his murders.
** "Conflicted" takes the cake of this trope, with an [=UnSub=] who is a cross-dressing serial killer alter personality who lures and disarms her victims sexually and then rapes them (penetratively). The cross-dressing is more convincing to the characters than to the audience, and to top it off, the [=UnSub=] has a habit of suddenly cross-acting without redressing.
* While TheMaster spends the majority of the ''Series/DoctorWho'' story ''The End of Time'' wearing a black hoodie, the climatic sequence where [[spoiler:the Master uses the immortality gate to transform nearly the entire global population into copies of himself, sees him don a variety of outfits. The sight of John Simm in a dress applauding himself while giggling insanely can also be counted as a CrowningMomentOfFunny.]]
* 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.
* ''Series/RedDwarf'' plays this trope for laughs a few times:
** In the season five episode "Demons and Angels", Lister is running for his life from the evil versions of the Red Dwarf crew, until he runs into Evil Rimmer, wearing what is best described as a Dominatrix-type get up.
** In another Series 5 episode, "Quarantine", when Rimmer contracts a holo-virus that sends him mad, he appears out of uniform, and holding [[HandPuppet Mr]] [[EnsembleDarkhorse Flibbles]]. Also lampshaded:
--->[Rimmer appears in an observation window. He is NOT in uniform.]
--->'''Rimmer''': Is something amiss?
--->'''Lister''': [trying to disguise the tremor in his voice] Amiss? God no. What could possibly be amiss?
--->'''Rimmer''': You don't think there's anything amiss? I'm sitting here wearing a red and white checked gingham dress -- and army boots -- and you think that's un-amiss?
* ''Series/{{Community}}'' Dean Pelton could be considered a WholesomeCrossdresser, as he's not a bad guy; but in-universe, most people are weirded out by his bizarre (often [[FanDisservice revealing]]) outfits, which puts him in the territory of this trope. It doesn't help that he's also a dalmatian furry fetishist with a [[StalkerWithACrush serious crush]] on one of his students. The students note a few times that he'd be less creepy if he would just admit he's a crossdresser, instead of constantly pretending to be forced to borrow clothes from his nonexistent sister.
* ''Series/{{JAG}}'': In "Retrial", a sailor had unbeknownst to him hired a transgender prostitute. When finding out, the sailor changed his mind and the prostitute threatens him with a knife.
* ''Series/ArrestedDevelopment'' has a few:
** Tobias would be "wholesome" in his motivation, but the results creep out pretty much everybody:
*** After Lindsey kicks him out, several episodes have Tobias dressing as an elderly British nanny so he can stay close to his daughter.
-->'''Narrator''': It was the [[LampshadeHanging exact plot]] of ''Film/MrsDoubtfire''.
** 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]].
** Barry Zuckerkorn goes to the City of Industry to pick up a prostitute, but quickly drives off when the prostitute reveals that she is ''not'' a man in drag. There are also some hints that Barry himself is a closet cross dresser.
** While he was hiding in the attic, George Sr. dresses in his late daughter-in-law's maternity clothes. During a hug, Michael also notes that he was wearing her perfume, too.
* ''Series/GuidingLight''. Brent Lawrence, after drugging and raping Lucy, faked his death, then returned to town as [[ShoutOut Marion Crane]], in order to befriend and ultimately terrorize his unsuspecting victim.
* In the ''Series/NYPDBlue'' episode "Andy Appleseed" (season 11), the detectives go to the apartment of a murdered woman because they think the suspected murderer may be there. They find him in her closet, trying on her bras and panties.
* ''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.
* ''Series/WhiteRabbitProject'': The ''Wardrobe Malfunction'' legend has this as one of the attempted escape shenanigans in the "Jailbreak" episode. A convict disguises himself as his visiting wife, trading places with her to escape. The title comes into play in that the convict was poorly disguised, couldn't act like a woman convincingly, and got recaptured within 15 minutes.

* The titular character in Music/PinkFloyd's first single, "Arnold Layne."
-->''Arnold Layne,\\
Had a strange hobby,\\
Collecting clothes,\\
Moonshine washing line,\\
They suit him fine!''
* Music/VelvetUnderground's "Sister Ray".

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

* "The Queen" of ''VideoGame/AliceIsDead''. He is a dangerous crime lord.
* Kefka is the only male character other than Cloud who is allowed to wear the crossdressing items in ''VideoGame/DissidiaFinalFantasy''. Then again, given that in the same game his official preferred weapons are ''flutes'' this might be an invocation of the RuleofFunny.
* Flea from ''VideoGame/ChronoTrigger''. A [[FanWank popular fan theory]] that made it into some fanfic was Flea, being from a race of monsters, doesn't worry about the details of what humans wear so much as wear what he thinks is cute.
** This may not quite excuse the official art having a bust.
*** It's a push-up bra apparently.
** [[http://i63.photobucket.com/albums/h128/Rikkuni/Chrono%20Cross/ePSXe2008-06-1615-46-07-76.png "She" is a cutie in the sequel, though.]]
* [[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.
* 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]].
* The ''VideoGame/SNKGalsFighters'' FightingGame has "Miss X", who is essentially the badass Iori Yagami in a sailor uniform and a bandit's mask. Predictably, no one in the rest of the all-female cast falls for it, and all of them point it out immediately.
* Gao from ''VideoGame/RhapsodyAMusicalAdventure''. In fact, due no doubt in large part to the graphical limitations of the game, it's actually near-impossible to tell it's a girl. She ends up giving a forced, out-of-place speech about how people can't tell she's a girl just before you fight her simply so the audience can know.
* ''VideoGame/GanbareGoemon'' is rife with these, the most prevalent being Sister Bismaru, Ebisumaru's descendant who dresses like a cross between a [[NunsAreMikos nun and a miko]].
* Justice from ''VideoGame/GuiltyGear'' counts, if only because of the huge crotch spike in her armor...
** There's also the tendency for people to identify mecha as male unless they look distinctly feminine. Even without the crotch spike, she looks sort-of gender-neutral, and thus would likely be identified as male at first glance.
** More obviously, Testament in the first game, which also doubles as the game where his gender is the most ambiguous (thanks to him practicing his VoiceOfTheLegion.) Later games make his gender more obvious and his change in allegiance make him more of a WholesomeCrossdresser.
* Kanan of ''VideoGame/SoulNomadAndTheWorldEaters'', according to Vitali. [[spoiler:Penn in the Demon Path]] counts as well.
* ''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]]
* In ''VideoGame/BlackSigil: Blade of the Exiled'', [[spoiler:Mondu after the world fusion]].
* A man in ''VideoGame/FableII'' is wearing a very crude attempt at a home-made woman's outfit. It turns out that he's insane and trying to feed people to his adopted family of goblin-like monsters. The game allows the player character to cross-dress, but no other characters do.
* In ''VideoGame/SaintsRow2'', ''VideoGame/SaintsRowTheThird'', and ''VideoGame/SaintsRowIV'' 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 {{Transgender}} through EasySexChange, if they so desire. This can go into "Creepy" territory instead of "[[WholesomeCrossdresser Wholesome]]" by having a hugely muscled man running around in a tiny dress or worse/more hilarious a string bikini and beating random passerby's to death with [[WrestlerInAllOfUs wrestling moves]] and [[GroinAttack nut punches]] when he isn't blowing their brains out or running them over in a tank. In the third game, there's also a [[GiantMook Brute]], an 8-by-4 foot mountain of muscle, dressed like a naughty schoolgirl in the dungeons of a S&M sex club. There is no context for it being there outside of the club is run by [[BigBad the Syndicate]] and it's funny.
* 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/TotalWarShogun2''-tie-in item, and geisha are some of the most badass units in that game.
* [[spoiler:Thomas [=MacLaine=]]] in ''VideoGame/DeadlyPremonition'', who at that point in the story has been in such a massive TraumaCongaLine as well as [[spoiler:being the villain's ReplacementGoldfish for the woman he actually loves]] that he's gone completely off the edge of sanity.
* [[spoiler:Rudy D'Avanzo]] from ''VideoGame/GrandTheftAutoChinatownWars''.
* Though Ghirahim from ''VideoGame/TheLegendOfZeldaSkywardSword'' has a pretty effeminately flamboyant appearance, he generally doesn't seem to be outright wearing ''women's'' attire, as would be true to this trope. Still, a few elements of his appearance seem to border on it, particularly in the way his face looks like it's covered in women's makeup, e.g. heavy pink eyeliner and white lipstick.
** Yuga from ''A Link Between Worlds'' is an androgynous male antagonist who is obsessed with beauty and perfection.
* ''VideoGame/{{beatmania}} IIDX 19 Lincle''[='=]s ''Lincle Kingdom'' event features Rche, one of the bosses of the event, representing [[SevenDeadlySins Pri]][[{{Pride}} de]]. He is dressed very femininely and his gender is often (but not always!) censored in [[AllThereInTheManual supplemental material]]. His name is a play on "[[{{Satan}} Lucifer]]", and his "attack" consists of him [[JumpScare suddenly]] transforming into a goat and firing at the [[PlayerCharacter Q-pro]].
* ''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]].
* [[http://megamitensei.wikia.com/wiki/Drag_Queen Undead Drag Queens]] appear as early-game enemies in ''Franchise/ShinMegamiTensei: Devil Summoner: VideoGame/SoulHackers''. You could potentially recruit them, but given that they're of the Dark affinity and you only get the ability to recruit Dark demons quite a bit later in the game, it's not worth it except for OneHundredPercentCompletion. Recruiting one (or getting one through fusion) reveals in the Compendium that they are men who somehow became zombies as a result of their devotion to cross-dressing.
* 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.
* The Thin Men from ''VideoGame/XCOMEnemyUnknown'' are revealed to all be genetically female in [[VideoGame/XCom2 the sequel]] (due to their males being [[GenderCide exterminated]] by the Elders in order to curb their ExplosiveBreeder tendencies). This presumably also applies to [[MouthOfSauron the Speaker]], who is an upgraded Thin Man.

[[folder:Visual Novels]]
* Either Zepar or Furfur from ''VisualNovel/UminekoWhenTheyCry''. One is female and one is male, but as for [[http://media.giantbomb.com/uploads/3/39130/1230766-29ynxoo_large.png which]] is [[http://media.giantbomb.com/uploads/3/39130/1230765-ezn7h4_large.png which]]...

[[folder:Web Comics]]
* ''Webcomic/LastRes0rt'''s Kurt Striaeta is not-so-ironically nicknamed "Geisha" and shown in his mugshot wearing a very feminine kimono. The surprising part is, he's actually one of the few "explicitly evil" criminals in the comic.
* [[spoiler:Chelsie Warner]] of ''{{WebComic/Concession}}'' is not technically a villain, but is definitely [[CreepyChild problematic]].
* Nicholas in ''WebComic/SamuraiPrincess'' has a very serious case of a bad man trying to be a woman. He has so far been shown in a geisha-like dress, a catsuit and, heaven forbid, a maid outfit.
* Red Mage from ''Webcomic/EightBitTheater'' often wears a dress for not always apparent reasons.
* A psychopathic but not overtly effeminate mook in a skirt appears near the end of ''WebComic/ShadowGirls''. Since he's also an obvious cyborg it's implied that what's under the skirt isn't exactly normal either.
* A female example in ''Webcomic/ElsannaBramStokersDracula'', where Elsa crossdresses as a Victorian gentleman. As a result, Anna (as Mina Harker's expy) does not have a good first impression of her.

[[folder:Web Original]]
* The Sailor Bubba meme features an obese hairy guy cosplaying as ''Franchise/SailorMoon'', and is a common stereotype of male to female cross-players (although there is [[AttractiveBentGender the other extreme]]). Once this one became too common and no longer "edgy", the [[Anime/CowboyBebop Man Faye]] meme took its place.
* In ''RolePlay/SurvivalOfTheFittest'' v2, Damien Carter-Madison comes across women's clothing inside a wardrobe... and starts playing dress-up. One of the outfits he tries on is a sailor fuku, of all things. Note that he is a well-known villain of that version.
* 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.
** Douchey [=McNitpick=] is hinted to be one in "The Next Top 11 Fuck-Ups"; he's stated to have a corset amongst his wardrobe and apparently does this enough to know the difference between a Georgian dress and a Victorian dress.
* [[http://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.
* ''WebVideo/TenLittleRoosters'' episode 3 has Miles [[spoiler:running around, wearing Lindsay's [[WebAnimation/{{RWBY}} Ruby Rose]] cosplay dress, complete with make up and lipstick.]]

[[folder:Western Animation]]
* In the WesternAnimation/JoeOrioloFelixTheCat episode [[Recap/JoeOrioloFelixTheCat1x08BlubberinoTheWhale "Blubberino the Whale"]], The Professor briefly disguises himself as a mermaid with a bowl of fruit just to tease the marooned and starving Felix. He quickly sheds the disguise and sicks a shark after Felix.
* HIM, the FlamingDevil from ''WesternAnimation/ThePowerpuffGirls'', 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.
* Sakko from ''WesternAnimation/SuperRobotMonkeyTeamHyperforceGo''.
* Ice Man, of all characters, has a go at this in the beginning of the ''WesternAnimation/MegaMan'' episode "Ice Age".
* 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."
* PlayedForLaughs in ''WesternAnimation/JimmyTwoShoes'', during a ZombieApocalypse. Jimmy sees Heloise about to consume what will turn her into a zombie; however, when she turns around, [[EyePop it's most definitely not Heloise]].
-->'''[[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 a genuine {{Transgender}} so much as a creepy male golfer who only crossdresses so that he can compete on the womens' tour.)
* In ''WesternAnimation/FostersHomeForImaginaryFriends'', there's a creepy looking bearded homeless man who wears a dress and keeps reappearing in some episodes.
* In ''WesternAnimation/BatmanTheBraveAndTheBold'' ComicBook/TheJoker disguises himself as an Amazon to try and kill Franchise/WonderWoman.
* In ''WesternAnimation/AmericanDad'', Roger goes out in public using male ''and'' female disguises.