Creepy Crossdresser

"How many times have I told that boy not to accept food from mortal enemies out for revenge, disguised as girls?"

— Shoubu's mother, Duel Masters

A Crossdressing 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 always "he") is evil or deranged. While the look of the Wholesome Crossdresser tends to gloss over the dissonance between genders, this trope often calls attention to it. Often, this crossdresser exaggerates Tertiary Sexual Characteristics without bothering to cover up secondary (or primary) ones. Makeup Is Evil is often involved. Frequently, the 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 Noblewoman's Laugh, and absolute narcissism. He also often has a crush on the Big Bad, The Dragon, or in more humorous works, the Chaste Hero.

Sometimes coincides with both Trans Equals Gay and Depraved Homosexual, for a lethal combination of stereotypes. May overlap with Disguised in Drag (or, very rarely, its Distaff Counterpart, Sweet Polly Oliver) if the character adopts a crossdressing disguise more often than seems strictly necessary and/or enjoys it. Also may overlap with Fan Disservice. For the opposite, see Wholesome Crossdresser and Embarrassingly Dresslike Outfit. See also Sissy Villain.

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Examples:

Anime & Manga

• Chapter 279 of Air Gear reveals that the villainous girl Shalott who dresses in a frilly dress and wears a hat is actually a guy.
• In Akazukin Cha Cha, Doris is the twin brother of Dorothy who is in love with their childhood friend Seravy, who has Belligerent Sexual Tension 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 Squicks Seravy out to the point he is usually very violent to Doris (and only to Doris.)
• Rosiel from Angel Sanctuary often skirts the line with his unusual outfits. Anti-Villain Belial also counts.
  • Played for Drama with Sevothtarte.
• Anohana: The Flower We Saw That Day: 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.
• Baikinman from 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.
• McCoy from the anime Bakuen Campus Guardress 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.... and he is built like a linebacker.
• Black Butler: In episode five of the second season, Alois 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.
• Hansel and Gretel of Black Lagoon are very fond of swapping clothes (and, more disturbingly, personalities) with each other. Which one's which gender, though, is anyone's guess.
• Bleach:
  • Charlotte Chuhlhourne is a flamboyant Magical Girl 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 pelvic area. His hair is very long and painstakingly curled and styled and he wears long, false eyelashes. In his Resurrection form, called Reina de Rosas, he transforms into a frilly, bikini-style tutu costume that is designed with the petals of a rose in mind. He's extremely proud of his 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. Yumichika claims she reeks of semen, and a resurrected Charlotte also identifies her as "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.
• Osamu from Bokura no Hentai 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 Wholesome Crossdresser Jun.
• In Brave10, one of the 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. Token Evil Teammate Kamanosuke has also used this to trick people back when he was a bandit.
• Code Geass examples:
  • Earl Kanon Maldini, the aide to Prince Schneizel. In the series, he is not shown as a crossdresser (but he is feminine looking enough and once jokes about aiding Schneizel in "his private affairs" as well), but the Code Geass novels not only say he is, but that he was persecuted for it until he met Schneizel and was hired as his assistant.
  • 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).
• Deadman Wonderland had an Anti-Hero example in the form of Choplin "Peacock" Sukegawa, who was a mix of this and Wholesome Crossdresser. He was a gay man in a relationship with a bisexual Gold Digger and after being bullied by his coworkers over his sexuality, upon finding his boyfriend cheating on him with a woman he snapped, accidentally killing her with his Blood Magic. After being sent to prison he began dressing like the woman he killed out of envy for her good looks, but aside from that was rather personable for a death row inmate. By the end of the story he drops the "creepy" part entirely, having found the confidence to adopt his own identity instead of hijacking someone else's.
• Examples from Fist of the North Star:
  • Yuda represents the essence of this trope, particularly as played in anime. Outrageous outfit, annoying laugh, and insanely self-absorbed and narcissistic personality. Also obviously, albeit not explicitly, a Depraved Bisexual.
  • 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.
• Flame of Recca'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 unperturbed, considering the much stranger people he's met at this point, except in being completely nonplussed and confused by the reformed Aoi trying to explain his complicated backstory.
• Fragments of Horror story "Magami Nanakuse" is about the eponymous author, a cruel personality who has a bizarre memetic influence on people when she makes weird gestures, or tics, and she imprisons people to watch them develop tics of their own so she can write about them. She also happens to be biologically male (though it's not clear whether she's been in drag or is trans), which the protagonist insults her for after being accused of being a faker and a liar herself, arguing that Nanakuse just as bad for dressing contrary to her sex.
• Fullmetal Alchemist (2003):
  • 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 Word of God, no one knows Envy's true gender — not even Envy).
  • The serial killer Barry the Chopper first appeared dressing as a woman when out delivering meat from his butcher shop. He kidnapped Winry and almost murdered both her and Edward.
• In The Garden of Sinners, 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.
• Ghost in the Shell: Stand Alone Complex has a special case in which Pazu's Psycho Ex-Girlfriend wants to kill him and take both his cybernetic body and his identity. Fortunately, the real Pazu won. There are just enough clues at the end of the fight to prove it.
• Haou Airen: Huo Long. His heart is in the right place, but he is a Triad member.
• 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 going to 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.
• Jakotsu from Inuyasha has a crush on Inuyasha (and flirts with Miroku and Sesshomaru), but later 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 so cute he wants to cut them off.
• JoJo's Bizarre Adventure:
  • Narciso Anasui from Stone Ocean might classify as this depending on who you ask, given his Sociopathic Hero nature. But he is technically part of the "good guys", so he might be in a different category of crossdresser.
  • Despite what his name may suggest, Mrs. Robinson from Steel Ball Run is both a crossdressing man and one of the creepiest Starter Villains of any Part.
• Kirby: Right Back at Ya! has Escargon, a Camp Gay villain with a not-so-subtle crush on his boss who has cross-dressed a few times (usually because said boss wanted him to).
• Yuuji Fukunaga from Liar Game starts off as this, but slowly pulls a Heel–Face Turn and becomes one of the main supporting characters while still making a better looking girl than most of the female cast combined.
• The bad guy in Lupin III: The Pursuit of Harimao's Treasure was Herr Maphrodite, who doubles as a Sissy Villain and Effeminate Misogynistic Guy, as well. The clothing and behavior during the villain scenes made him creepy long before we find out who he really is.
• "Miss Aki," an unattractive example from Magical Shopping Arcade Abenobashi.
• Mariya from Maria†Holic 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.
• Lady Bat from Mermaid Melody Pichi Pichi Pitch.
• Monster offers a particularly creepy example in which this trope is not played for laughs. 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.
• Michio Yuki of manga series, MW, cross-dresses as his female victims after killing them.
• In My Bride is a Mermaid, 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 Dating Sim). The end result completely horrifies EVERYONE else, especially the two girls. Seeing the anime equivalent of the Terminator wearing a sailor fuku is not a pretty sight. Funny, but not pretty.
• Naruto:
  • Orochimaru of Naruto, who is actually a man 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... wearing Sailor Fuku. UGAH!
  • Gai on occasions in Rock Lee's Springtime of Youth.
• One Piece 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). Though after losing, he pulls a Heel–Face Turn, like many One Piece villains, transforming into a Wholesome Crossdresser.
  • Taken to absurd levels with Emporio Ivankov, the "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. When a pirate attacked him, berating him for having transformed his father into a woman and humiliated his whole family, Ivankov transformed him into a woman too and mocked him, sending him fleeing in tears. 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 a commander of the 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 Evil Versus Evil).
  • Zigzagged with the inhabitants of Kamabakka Kingdom, the original followers of Emporio Ivankov. They're certainly creepy looking, since they are very bad at crossdressing — simply throwing on cutesy female clothes and makeup on unshaven and hideously masculine bodies. But they're presented as being fundamentally decent people who don't want to hurt anyone. But then again, they're also very bad at taking "no" for an answer when it comes to guys not wanting to become "okama" like themselves. And yet at the same time, they were also instrumental in helping Sanji get stronger during the Time Skip.
• Suzu in Peacemaker Kurogane dresses in a more feminine manner after becoming gay and insane. He wears nail polish, makeup, revealing clothes, and sometimes wears a long, black fur robe (without wearing anything else underneath).
• Count D in Petshop Of Horrors is good friends with a group of drag queens and transvestites, and his peacocks also appear this way in their 'human' forms.
• Pokémon: The Series 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.
• Even Pretty Cure got in on this, as Phantom, the Pretty Cure Hunter, went into battle as Cure Un-Lovely, a Cure Lovely lookalike dressed in red and black, in one episode.
• Tsubasa Kurenai from Ranma ½. 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 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 is a boy.
• Kamatari of Rurouni Kenshin, though he's portrayed fairly sympathetically and is driven by an unrequited love for Shishio. Otowa, on the other hand, is just a Psycho for Hire.
• The Big Cheese from Samurai Pizza Cats. Strangely, his flirting with male subordinates was mostly left intact in the English dub.
• Fish Eye from Sailor Moon has shades of this, though is clearly intended to appeal to the fetish. As the other villains disguise themselves, the Hand Wave is dressing as a woman is simply a modus operandi to cover the 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 closer to Earth, and he has the first Heel–Face Turn of the season. In the manga, Fish Eye doesn't do this, but it applies to Tiger's Eye instead.
  • 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.
• Sakurako from Sakura Gari 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 Villainous Breakdown and committed suicide.
• Tamagotchi gives us a decidedly more innocent example. In one episode, Himespetchi's crush on Mametchi reaches the point where she crossdresses as him. While it's unsettling to everyone else, she's not being outright malicious.
• One early example of this trope would be Rock, from the various manga by Osamu Tezuka. Who, in his more villainous incarnations, would often disguise himself as a woman.
• Elendira the Crimsonnail from 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 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 goes Million Winged Angel. (Meanwhile, 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.
• Fumiya Ninomiya from Wandering Son 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.
• Welcome Back, Alice: Before the audience knows anything about their motivations, Kei comes off as a stereotype of a perverted crossdresser, using their androgynous appearance to sexually tease their friends.
• Marube from Yuureitou is obsessed with becoming beautiful to the point where he would do anything to become a female including attempting a brain transplant with his son Tetsuo. In his final appearance he's dressed as a woman, and a very attractive one despite being in his forties, but is very unhinged.

Comic Books

• In American Flagg!, Ivor Overholt, who makes himself into a doppelganger for the presumed-dead Peg Krieger in order to seduce and blackmail a character who was obsessed with her. Possibly a borderline example of Easy Sex Change as well, though the character still had his original genitalia and still appeared as a man in public.
• In Grant Morrison's Arkham Asylum: A Serious House on Serious Earth, the Joker was originally going to be sporting a costume with Madonna's signature cone-shaped bra and stilletto boots, simply because he knew it would make Batman highly uncomfortable.
• 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 Lori Lovecraft: Into the Past, Moral Guardian and mayor of Los Angeles C. Aubrey White turns out to have had a previous career as a transvestite prostitute called 'Lola'. He readopts the Lola guise to murder those who know the truth and can expose him.
• One comic book in the Plants vs. Zombies series has the evil Dr. Zomboss dress up in several costumes in order to sneak into a human book club and eat their brains, with one costume being a rebellious cheerleader. He later dresses up as a zombie version of Marie Antoinette as part of the book club's themed meetings, and is seen drooling when the club's leader comments that seeing the costumes are stimulating her brain.
• The Punisher (2001) had The Russian, an Ax-Crazy Cyborg Husky Russkie whose augmentations involved hormone injections that resulted in him growing giant boobs. He took this in stride and started wearing women's clothing, with Spider-Man calling him "Giant-Sized Ma'am Thing".
• The Purple Marauder, transvestite women-hating archnemesis of the Anti-Hero 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.
• Wonder Woman:
  • Golden Age foe Blue Snowman was a rare female version of this, being a woman who dressed up in a male snowman outfit to commit crimes.
  • Wonder Woman (1942): Maru is a very pretty Japanese woman whose disguise as Dr. Poison makes her look like a wrinkles unattractive man.
  • Hypnota wears fake facial hair and dons a phony French accent to pass herself off as a man, and has an Ambiguous Gender Identity as they and their sister usually use male pronouns to refer to Hypnota. In the Post-Crisis stories, this aspect was dropped and she's referred to as Hypnotic Woman.

Comic Strips

• Sanjak from Terry and the Pirates is a rare female version. A Frenchwoman who dresses like a man, using a monocle to hypnotize people, and displays a sexual interest in Terry's girlfriend April Kane. She works for the Axis, impersonating a pilot to infiltrate Terry's Air Force base.

Fan Works

• Evangelion 303: Saburo starts to cross-dressing as part of a plan to win Kaworu back. However Kaworu finds it creepy and unsettling.
• A Homestuck fanart calendar featured a badly-crossdressing Eridan Ampora in the March page as a joke. The "March Madness" outfit caught on and became a fandom meme, even making a cameo appearance in the Ministrife updates.
• In Thirty Hs, Harry Potter wears women's underwear. The inquisitors wear them too. Because of this, they realise they are all men of the Lord.

Films — Animation

• Snatcher performs as Madame Frou Frou to spread fear of The Boxtrolls.
• Played for Laughs in The Super Mario Bros. Movie when The Dragon Kamek dresses up as Princess Peach to help Bowser practice his proposal to her.
• As a part of his master plan in Teen Titans Go! To the Movies, Slade disguises himself as the female Jade Wilson.

Films — Live-Action

• In 31, Death-Head wears a tutu.
• Ace Ventura: Pet Detective has the villain Lois Einhorn, who is actually disgraced football player Ray Finkle, who had stolen the identity of a missing hiker. The creepiness is less because of appearance, as it's a Fair Cop who impresses the men around (to the point that Ace is 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.
• After the climax of Alvin and the Chipmunks: The Squeakquel, Ian Hawke tries to stand in for the Chipettes after he lost them, failing spectacularly.
• Deconstructed and Played for Laughs in Austin Powers: International Man of Mystery. Austin is used to spotting and de-wigging evil assassins disguised as women, as befitting a Campy Tuxedo and Martini spy flick, essentially rendering him Wrong Genre Savvy in The '90s. This leads to him knocking back Basil's poor mother and trying to pull her wig off.
• In Beyond the Valley of the Dolls, the character 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.
• Black Rat: It turns out that there are actually two Black Rats: Ajura's sister Akane, and Keno, who wears the same schoolgirl uniform and rat mask.
• Both Frank Booth and Ben, two villains from Blue Velvet, deserve some mention here as they both wear feminine makeup at some point in the movie.
• The Boondock Saints: While the character is heroic, detective Smecker's crossdressing disguise is played to be comically off-putting. The fact that he's played by Willem Dafoe helps.
• The Borrower: 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.
• Played distressingly straight in the otherwise comic 60s caper flick Caprice, in which it’s revealed that villainous Stuart Clancy got into the fashion industry so he could wear women’s clothes.
• The Celluloid Closet: One scene from Freebie and the Bean is pointed out where a depraved crossdresser is murdered in cold blood, and how audiences in the theater cheered it loudly.^note After a lengthy chase, the “transvestite” villain shoots Bean, seriously injuring him, and Freebie faces him in a final showdown in a bathroom at the baseball stadium. Freebie is beaten at first, knocked on the ground by the “transvestite” who interrupts his kicks and punches for a little preening time, but eventually Freebie manages to grab a gun and empties it into the transvestite’s chest. Audiences reportedly cheered at the death scene, not just happy for the villain’s demise but cheering “the death of the fag.” Notably, the shooting was deemed too violent for network reruns of the film, who removed several of the gunshots to reduce it down to just two. — Queer Blog-a-Thon
• In Chai Lai Angels: Dangerous Flowers, the Big Bad's chief lieutenant is a crossdresser (implied to be transgender) nicknamed King Kong. He is prone to throwing hissy fits whenever thing don't go his way.
• While committing murders, Leonard Marliston from Cherry Falls dresses like his mother.
• In The Dark Knight, 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 invoked, seeing as he'd kept his Joker face paint 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).
• Dead Man: In The Wild West, William Blake happens upon three men camping in the woods, two looking like mountain men and one (played by Iggy Pop) wearing a woman's dress and bonnet. The trio behave very strangely before revealing that they're going to kill Blake as part of some biblical ritual.
• In Death Spa, David has taken to dressing as his dead sister Catherine, although not entirely voluntarily.
• In Death Walks on High Heels, Crusty Caretaker Hallory is revealed to be a creepy crossdresser when Michel and the police discover him him dancing around the cottage where Nicole was murdered wearing a wig and gown belonging to her.
• In Death Wish V: The Face of Death one of the villains is Fredrick "Freddie Flakes" Garrity (not at all played by Sid the coroner from CSI: NY), 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).
• Doctor in Trouble: After finding a shoeless Dr. Burke in Ophelia's cabin with a dress wrapped around his neck and a pair of women's shoes on the floor, the Master-at-Arms gets the wrong idea and assumes he's "one of them".
• Dressed to Kill: It turns out that Michael Caine's character was the killer all along and is a cross dresser, as referenced by the title. The final scene has him strangle a nurse and steal her outfit to escape the mental asylum.
• In Filth, the main character is this, although, frankly, he's creepy independently of this habit and the actual crossdressing is played for sympathy.
• Freebie and the Bean, a buddy cop film from the 70's, features a beautiful blond crossdressing antagonist played by Christopher Morley.
• In Fresh Meat, Ritchie takes Rina to her room to exploit her sexually. He dresses in her bra and panties and while she pretends to be interested in him, bites his crotch until it bleeds, forcing the other criminals and family back into the same area. According to Rina, he didn't get hard untill he put on her bra and panties.
• One of the killers in Ghostland is a man wearing a dress and black wig.
• Loco in The Great Silence is a downplayed example who is not Played for Laughs. As noted in the original Italian version, he "wears a priest's hat and a woman's scarf".
• Grom: A Rough Childhood has a downplayed example with the villain Anubis, who—though modeled after the male deity of ancient Egypt—is revealed to be the female chief of police. The protagonist, Konstantin Grom, is able to discern the killer's identity as soon as he gets close, thanks to the familiar scent of her cigars and "old lady perfume".
• Lord Voldemort from Harry Potter was apparently one, according to Ralph Fiennes.
• 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.
• Dark from 2002's Hunting Humans. As Something Awful 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."
• James Bond:
  • Thunderball has an old enemy of Bond disguised as his own "widow".
  • Blofeld undertook a spot of cross-dressing (although it was technically a desperate disguise) in the film adaptation of Diamonds Are Forever.
• Real Life 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.
• In Night After Night After Night, the Serial Killer disguises himself in drag to evade the police after he is almost caught, and the presence of wigs, makeup and women's clothing in his lair indicates that this is not a new activity for him.
• In On the Buses, Mavis assumes Blakey is wearing frilly pants and a black suspender belt under his mac when she believes he has tried to steal her friend's knickers.
• Pirates of the Caribbean: The Curse of the Black Pearl sees 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 (some of whom react favorably). Pintel is decidedly unhappy.
• Psycho: Infamously, Norman Bates dresses up as his mother while murdering people.
• Dr. Frank N. Furter from The Rocky Horror Picture Show. Also a Depraved Bisexual, not that anyone's complaining. An unusual example of the trope because his crossdressing isn't portrayed as disgusting or ugly in itself (though it shocks the more sheltered characters); instead, it's treated as part of what makes him so attractive and charismatic, with his attractiveness and charisma in turn being used to manipulate and abuse people. (Richard O'Brien, the writer of the film, is queer and a crossdresser himself, and accordingly created the character as someone to either envy or be attracted to rather than purely someone to be horrified by, depraved though he is.)
• Harry Russo from Schizophreniac The Whore Mangler and its sequels, apparently the result of his horribly abusive parents wanting a girl.
• Dickie from Set The Thames On Fire wears short, girly dresses and exaggerated makeup throughout the movie, all the while acting in a manner that can be described as creepy. However, Dickie doesn't seem to have any bad intentions, and any of his creepy behavior towards the main characters can be chalked up to a misunderstanding.
• In Shine, David (it's implied) sleeps with one while he is studying in the Royal College of Music.
• Buffalo Bill from The Silence of the Lambs. 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.
• Angela turns out to be one in the famous Twist Ending of the Slasher Movie Sleepaway Camp. To be fair though, Peter was forced to take his dead sister's identity by his demented aunt.
• In Stripped to Kill, the Serial Killer turns out to be Roxanne's brother Eric who has killed his sister and adopted her identity, including dancing at the strip club in her place.
• In Terror Train, the killer Kenny has come on board the train disguised as the Magician's Lovely Assistant.
• Leatherface is a crossdresser in Texas Chainsaw Massacre: The Next Generation. The character was loosely based on real-life killer Ed Gein in the first place anyway, so it makes at least some kind of sense, unlike the rest of the movie.
• The Toxic Avenger: One of the two thugs in Cigar Face's street gang is a crossdresser in a dress, wig and make-up. While the Toxic Avenger is ripping his buddies apart, the crossdresser stands aside to reapply his make-up before joining the fray.
• Marion Penrose in Unhinged (1982), due to his mother being an insane misandrist.

Folklore

• One Urban Legend features a serial killer disguised as an old woman who asks passerby to help "her".

Literature

• Ascendance of a Bookworm has Justus, a Seeker Archetype 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 Disguised in Drag. 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 Cloudcuckoolander's Minder to watch him to not wanting him inside it at all when he seriously offers to cross-dress to avoid making the Does Not Like Men adult residents of the girl's building uneasy.
• Child of God: After Lester becomes a full-on serial killer, he starts wearing the clothes of his female victims. At first it comes across as Lester, a homeless man who lives primarily in caves at this point, wearing any clothes he can get his hands on, but towards the end of the book it's mentioned that he made at least one wig out of a scalp.
• Antiheroic example in 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?
• Ellery Queen: The murderer in The Last Woman is His Life is one. It is the reveal of him being this (and a Depraved Homosexual) and the victim's reaction that drives him to murder.
• I, Claudius features a scene where Caligula 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.
• Jaine Austen Mysteries:
  • In The PMS Murder, Pam Kenton disguised herself as a male building inspector to get into Rochelle's and mess with the guacamole, and later dresses as a male employee of the hotel Jaine is going to to kill her.
  • Fiona Williams from Death of a Trophy Wife can pass herself off as a man pretty well, which comes in handy when she lures out Bunny's maid Lupe to silence her.
  • Barnaby, the killer of "Nightmare on Elf Street", dresses up as a sort of grandma character while murdering Scotty.
  • In Death by Tiara, Jaine discovers pageant judge Dr. Edwin Fletcher, is a crossdresser, and was being blackmailed by Candace over it. He only really goes into the "creepy" territory when he attacks Jaine to scare her out of talking. He's also not the killer.
• "Why Grandma, what big eyes you've got!" The Big Bad Wolf from Little Red Riding Hood is one of the oldest ones in the book, dressing up as the title heroine's grandmother.
• The Machineries of Empire, "Extracurricular Activities": Jedao has to steal a medic's clothes during an infiltration Indy Ploy, which he does despite the medic being a woman. They keep him from being identified as an enemy operative and he's androgynous enough to make the disguise work, but he keeps getting appalled stares and isn't sure why.
• Bèbelle from Malevil. Part of it is being creepy and evil, another part is using Disguised in Drag to infiltrate settlements prior to his marauding army invading.
• Herman Goering was depicted as a transvestite in A.E. Hotchner's novel The Man Who Lived at the Ritz.
• In 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 Take That! against Grady (who is a trans boy).
• 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.
• In the 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 Mirror Monologue 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..."
• Troubled Blood, the fifth installment of the Cormoran Strike series by Robert Galbraith, features Dennis Creed, a serial killer who dresses as a woman to lure his victims into a sense of false security (although he ultimately turns out to be a false lead in the murder investigation at the center of the novel's plot).

Live-Action TV

• Arrested Development:
  • After Lindsey kicks him out, several episodes have Tobias dressing as an elderly British nanny so he can stay close to his daughter. It would be "wholesome" in his motivation, but the results creep out pretty much everybody.
    Narrator: It was the exact plot of Mrs. Doubtfire.
  • 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 doesn't even 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.
• The Big Bang Theory has a transvestite who used to live across from Sheldon before Penny moved in. He's shown once, in an outfit clearly designed for weirdness and comedic effect, leading to the punchline of him describing Sheldon as "the crazy guy across the hall", as if Sheldon's weirdness must be exceptional for someone who looks like that to call him "crazy".
• Community Dean Pelton could be considered a Wholesome Crossdresser, as he's not a bad guy; but in-universe, most people are weirded out by his bizarre (often 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 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.
• Criminal Minds:
  • "Machismo" was Ripped from the Headlines 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. Even when he was just a serial rapist beforehand, they utilised crossdress, but that's likely because it makes it easier to be under the radar until they attack/when they leave after the assault.
  • 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.
• Doctor Who: While the Master spends the majority of "The End of Time" wearing a black hoodie, the climatic sequence where 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 seen as funny.
• When Luke and Laura on General Hospital went on the run in 1980, they eventually encountered Sally, a hitman who wore a dress.
• Ghostwatch is a British ghost investigation Mockumentary featuring a poltergeist named "Mr. Pipes" by the family living in the house. Despite the whimsical name, Pipes is the frightening and sinister spirit of a crossdressing paedophile named Raymond Turnstall, who lived in the house as a lodger in the 1960s and hanged himself in the basement. He sometimes appears in the background as a menacing figure in a black dress with a Skull for a Head (his cats ate his face when he died).
• Guiding Light. Brent Lawrence, after drugging and raping Lucy, faked his death, then returned to town as Marion Crane, in order to befriend and ultimately terrorize his unsuspecting victim.
• 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.
• LazyTown: Robbie has cross-dressed several times to further a scheme, like as a birthday fairy, a fortune teller, and a manners teacher.
• The male conspirator who murders Georgia Trotman in Line of Duty is disguised as a nurse.
• The Miami Vice pilot, "Brother's Keeper," features a hitman whose signature method of killing is to dress as a woman so as to conceal himself from his intended victims until it's too late for them to react.
• Whiterose, the Big Bad of Mr. Robot, first appears to Elliot dressed as a woman, but later seemingly appears in public as the male Minister Zhi Zhang. At first the series is vague on what is going on with Zhang and Whiterose; Zhang claims that his collection of dresses belongs to his sister, and the two are shown having conversations at several points. The final season reveals that Whiterose is transgender, and she's planning on shedding the Minister Zhang persona as soon as she's taken over the world.
• In the NYPD Blue 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.
• The Outer Limits (1995): 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.
• Alonzo Torquemada of HBO's 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.
• Red Dwarf plays this trope for laughs a few times:
  • In "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 "Quarantine", when Rimmer contracts a holo-virus that sends him mad, he appears out of uniform, and holding Mr 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?
• Borderline-ish example: the second season of Skins features a 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, who happens to be gay. It doesn't work.
• Victorious: Jade spends a night at Cat's house for a sleepover. When she wakes up, she notices that Cat's brother stole her bra and is wearing it.
• White Rabbit Project: 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.
• Wire in the Blood has an extreme Values Dissonance example where a MtF transwoman is believed to actually be a Depraved Homosexual by the therapist protagonist, making the scene where the protagonist is kidnapped and tortured the epitome of this.

Music

• The titular character in Pink Floyd's first single, "Arnold Layne."
  Arnold Layne,
  Had a strange hobby,
  Collecting clothes,
  Moonshine washing line,
  They suit him fine!
• Velvet Underground's "Sister Ray".
• New York Dolls played up this image by wearing trashy women's clothing on stage.

Pro Wrestling

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

Video Games

• "The Queen" of Alice Is Dead. He is a dangerous crime lord.
• beatmania IIDX 19 Lincle's Lincle Kingdom event features Rche, one of the bosses of the event, representing Pride. He is dressed very femininely and his gender is often (but not always!) censored in supplemental material. His name is a play on "Lucifer", and his "attack" consists of him suddenly transforming into a goat and firing at the Q-pro.
• In Black Sigil: Blade of the Exiled, Mondu after the world fusion.
• Monsieur Scarlet from Bug Fables wears red effeminate attire with a dress, damsel hat, and a pink umbrella, and he is also a Serial Killer who preys on unsuspecting exploration teams via luring them with false help requests and then draining their life-force to the husk. Ironically, he is the only male ant encountered in the game.
• Flea from Chrono Trigger. A 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. His official art even has a bust (he wears a push-up bra).
• Doc Fingers in Cyberpunk 2077, a perverted Mad Doctor 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 Femme Fatalons. What makes him even creepier is that he's infamous for giving his patients (primarily struggling prostitutes) low-quality cybernetics, forcing them to frequently come back for repairs or replacement while accepting "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 (and resist the urge to beat him to death).
• Dark Sun Gwyndolin from Dark Souls 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.
• Thomas MacLaine in Deadly Premonition, who at that point in the story has been in such a massive Trauma Conga Line as well as being the villain's Replacement Goldfish for the woman he actually loves that he's gone completely off the edge of sanity.
• Kefka is the only male character other than Cloud who is allowed to wear the crossdressing items in Dissidia Final Fantasy. Then again, given that in the same game his official preferred weapons are flutes this might be an invocation of the Rule of Funny.
• A man in Fable II 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.
• Final Fantasy Tactics A2: The Night Dancer is a cross-dressing Camp Gay 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.) [1]
• Ganbare Goemon is rife with these, the most prevalent being Sister Bismaru, Ebisumaru's descendant who dresses like a cross between a nun and a miko.
• In Grand Theft Auto: Vice City, during the mission "Psycho Killer," Tommy Vercetti must chase down and kill a psycho who's dressed as a woman who "wants to see Love Fist burn" after the band "ruined his life." His deep voice doesn't help the creepiness.
• In Grand Theft Auto V, Trevor can buy and wear dresses, which naturally invokes this reaction from passerby. One scene when you switch to him also sees him waking up from a drinking binge atop a mountain in a dress.
• Justice from Guilty Gear 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 Voice of the Legion.) Later games make his gender more obvious and his change in allegiance make him more of a Wholesome Crossdresser.
• Though Ghirahim from The Legend of Zelda: Skyward Sword 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.
• Tamamo no Mae from Onmyōji who often assumes the form of a woman (which is also his Awakened appearance) to go around wreaking havoc. This and his voice actress makes him the victim of a lot of Viewer Gender Confusion.
• Plants vs. Zombies 2: It's About Time: 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 midget male zombie with an oversized brain.
• Alfred Ashford from Resident Evil – Code: Veronica is already creepy on his own with his mannerisms and tone of voice, but his crossdressing only serves to make him even creepier. Due to his upbringing being very screwed up, he had a rather "close" bond with his twin sister before she went missing. Alfred's mind got so messed up that he'll dress up as his sister and even talk and act like her. When Claire finds out about his crossdressing secret, she calls him a crossdressing freak the next time they meet.
• Gao from Rhapsody: A Musical Adventure. 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.
• In Saints Row 2, Saints Row: The Third, and Saints Row IV 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 Transgender through Easy Sex Change, if they so desire. This can go into "Creepy" territory instead of "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 wrestling moves and 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 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 the Syndicate and it's funny.
• Undead Drag Queens appear as early-game enemies in Shin Megami Tensei: Devil Summoner: Soul Hackers. 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 100% Completion. 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.
• The SNK Gals Fighters Fighting Game 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.
• Kanan of Soul Nomad & the World Eaters, according to Vitali. Penn in the Demon Path counts as well.
• Kamek from the Super Mario series dons Princess Peach's dress and a wig as a disguise in both New Super Mario Bros. U and Mario & Luigi: Dream Team....and, in the latter, accidentally confirms that he likes wearing the dress. Mario & Luigi: Partners in Time also sees him wearing a frilly, white lace apron over his usual robe.
• The Medic in Team Fortress 2, sort of. He has an unlockable wig that's in a Geisha style with a comb and small flowers, leading to a Broken Base over those who thought Valve was pandering to the fans who wanted more Ho Yay (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 Total War: Shogun 2-tie-in item, and geisha are some of the most badass units in that game.
• The Thin Men from XCOM: Enemy Unknown are revealed to all be genetically female in the sequel (due to their males being exterminated by the Elders in order to curb their Explosive Breeder tendencies). This presumably also applies to the Speaker, who is an upgraded Thin Man.
• One of the "Majima Everywhere" encounters from Yakuza Kiwami is "Goromi-chan", AKA Majima in a pink go-go dress, fishnets, high heels, and a blonde wig. All in the name of sweet talking "Kiryu-chan" into getting in to a drag-out fight in the street when Kiryu "spurns" him.

Visual Novels

• Danganronpa V3: Killing Harmony plays with this trope; Tsumugi is the Ultimate Cosplayer, which means she is revealed to be a very adept at crossplaying as well. This would fall under the Wholesome Crossdresser trope if it weren't for the circumstances in which she shows off this talent, namely that she's using her talent to cosplay and crossplay as all the previous Danganronpa protagonists, revealing that she's the true ringleader of the killing game and that the previous Danganronpa characters were all fictional characters.
• Phoenix Wright: Ace Attorney – Spirit of Justice has Queen Ga'ran Sigatar Khura'in, who dressed herself up in the clothes and attire that belonged to the corpse of her brother-in-law Dhurke Sahdmadhi as part of a Dead Person Impersonation in her effort to frame him for the murder of her Hero Killer husband Inga Karkhuul Khura'in.
• Either Zepar or Furfur from Umineko: When They Cry. One is female and one is male, but as for which◊ is which◊...
• Rio Ranger, the Arc Villain of Your Turn to Die chapter 2-1, is a Rummage Sale Reject who happens to wear a skirt. The other characters would have found it unremarkable if not for the fact that he stole these clothes from dead participants.

Webcomics

• Red Mage from 8-Bit Theater often wears a dress for not always apparent reasons.
• Chelsie Warner of Concession is not technically a villain, but is definitely problematic.
• A female example in Elsanna – Bram Stoker's Dracula, 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.
• Last Res0rt'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.
• Nicholas in Samurai Princess 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.
• A psychopathic but not overtly effeminate mook in a skirt appears near the end of Shadow Girls. Since he's also an obvious cyborg it's implied that what's under the skirt isn't exactly normal either.
• Unsounded: Ruckmearkha—a giant, monsterous, soul eating 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 Roger, his latest braindead victim, in a bag under his dress.

Web Original

• The Sailor Bubba meme features an obese hairy guy cosplaying as Sailor Moon, and is a common stereotype of male to female cross-players (although there is the other extreme). Once this one became too common and no longer "edgy", the Man Faye meme took its place.
• In Survival of the Fittest 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.
• Ten Little Roosters episode 3 has Miles running around, wearing Lindsay's Ruby Rose cosplay dress, complete with make up and lipstick.
• Channel Awesome:
  • As another plan to get in Todd in the Shadows's pants, The Nostalgia Chick 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.
• A fan video for Mr. Bungle'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 recurring shots from his point of view where the woman is dressed elegantly instead of in casual clothes - at the climax he tracks her to her home and starts attacking her and forcibly smearing lipstick on her face too, but in the shots from his perspective he's in a suit, she's still in a formal dress, and they're simply having a romantic slow dance together.

Western Animation

• Adventure Time: At the end of Season 6, Princess Bubblegum is usurped by the King of Ooo as ruler of the Candy Kingdom. In "Varmints", one of the first episodes of Season 7, Marceline pops into Bubblegum's old bedroom to find the King wearing a wig and Bubblegum's pajamas.
  King of Ooo: Tell Bubblegum I wear her nightgown! Tell everyone!
• In American Dad!, Roger goes out in public using male and female disguises.
• In Batman: The Brave and the Bold The Joker disguises himself as an Amazon to try and kill Wonder Woman.
• In The Fairly OddParents!, Timmy manages 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."
• In the Felix the Cat (Joe Oriolo) episode "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 sics a shark after Felix.
• In Foster's Home for Imaginary Friends, there's a creepy looking bearded homeless man who wears a dress and keeps reappearing in some episodes.
• Played for Laughs in Jimmy Two-Shoes, during a Zombie Apocalypse. Jimmy sees Heloise about to consume what will turn her into a zombie; however, when she turns around, it's most definitely not Heloise.
  Dorkus: You, uh, probably shouldn't tell Heloise about this.
  Jimmy: Really, I wouldn't know how.
• In a King of the Hill Christmas Episode, Straw Loser Bill's seasonal depression stemming from his ex-wife Lenore leaving him worsens to the point he's Driven to Suicide. After a series of shenanigans with the gang foiling multiple attempts, he has a nervous breakdown and out of a desperate desire to reconnect with his wife starts trying to act like her, putting on a dress and speaking in a high-pitched voice like a fat, balding Norman Bates. He later crashes Hank's Christmas party during this, and the other Good Ol Boys in attendance get the wrong idea and start harassing him under the belief he's some pervert, until Hank saves the day by putting on a dress himself to play it all off as a joke.
• Ice Man, of all characters, has a go at this in the beginning of the Mega Man (Ruby-Spears) episode "Ice Age".
• The Simpsons: In the episode "There is Something About Marrying", pro golfer Veronica is 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 Transgender so much as a creepy male golfer who only crossdresses so that he can compete on the womens' tour.
• HIM, the Flaming Devil from The Powerpuff Girls (1998), usually dresses in a fuzzy pink skirt and thigh-high stiletto boots. His voice also tends to shift between falsetto and a deep growl depending on his mood.
• Sakko from Super Robot Monkey Team Hyperforce Go!.

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