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Incredibly Conspicuous Drag
I agree, it's not my best disguise, but I had to make do.

"How it becomes clear that he is not a woman is not nearly as interesting as how anyone could possibly have thought he was a woman in the first place. He plays a woman as if determined, in every scene, to signal to the audience that he's absolutely straight and only kidding."
Roger Ebert on Matt LeBlanc in All the Queen's Men

Somebody passing for the other gender is a common trope in comedy, all the way back to Shakespeare. However, it usually works only if the actor in question actually makes an effort to look and behave like a member of the opposite sex, otherwise the audience's Willing Suspension of Disbelief is broken and instead of being about, say, a man trying to pass as a woman, the work becomes about how a group of morons didn't realize they were trying to pick up a drag queen. Occasionally it works, if applied side by side with Rule of Funny.

Compare Paper-Thin Disguise. A Sister Trope to Larynx Dissonance and (naturally) Disguised in Drag.


Examples:

    open/close all folders 

     Anime and Manga  
  • Abenobashi Mahou Shoutengai's Crossdresser "Ms." Aki. is never outed, but is rather obvious — so much so that it seems the rest of the cast is aware of it and just treats him/her as a lovable eccentric.
  • All the crossdressers from One Piece are incredibly ugly and clearly don't shave, though they still behave much like women. The only exception so far is the secondary character Izou: The only thing that gives away his sex is his lack of a cleavage.
  • In Penguin Revolution, the talents and managers of Peacock are required to dress in drag for a publicity event. Most of the actors pull it off remarkably well, but Kaneda, one of the managers, just looks like a man in a dress.
  • Mad Bull 34 takes the cake, here. The "Mad Bull" himself, an eight-foot-tall muscular behemoth of a police officer with a full beard and mustache, goes undercover as a nun and as a female prostitute. He somehow expects this disguise to work.
  • Sven in the anime of Black Cat refused to allow Eve to serve as a Dirty Harriet in order to lure out a Serial Killer who targets women, so he does so himself and doesn't even bother shaving his beard.

     Comic Books  
  • The Beagle Boys in Donald Duck comics. They still wear their masks, and don't shave.
  • Aversion in a Don Martin cartoon for MAD: Men looking for an escaped convict at a train station see a hairy-armed, tattooed, stubble-faced person in a dress walk by. One of them pulls off the person's wig and they jump on the presumed escaped convict... but let her go with shamefaced apologies.
  • Jokey Smurf in The Smurfs one-page gag in "Romeo And Smurfette", who disguises himself as Smurfette (not perfectly) in order to fool a Smurf into a Prank Date. Needless to say, the Smurf was neither fooled nor amused.
  • The National Lampoon had a comic-book style ad for magazine subscriptions with two clearly middle-aged men (one had a moustache, the other stubble and a cigar) dressed like housewives at a supermarket. They addressed each other with female names, the employees regarded them as women, then the last panel had the police turn up and haul them off. None of this was explained in the least.

    Film 
  • As the page quote indicates, the WWII comedy All the Queen's Men (allegedly Based on a True Story) completely destroys any possibility of seeming authentic because the actors (including Eddie Izzard) make absolutely no attempt to be believable as women.
  • A number of the Carry On films involve Sid James or Bernard Bresslaw (or another similarly unmistakeably masculine cast member) wearing a dress, and the authority figure they're trying to evade falling instantly for him, despite the fact that he's clearly Sid James or Bernard Bresslaw wearing a dress. (The fact that the authority figure was frequently Kenneth Williams may add a bit of subtext to this.)
  • Played for Laughs in Gangs of New York when an incredibly obvious transvestite (stubble and all) shows up to a dance where males are paired with females. He, of course, goes to the "female" side.
  • Subverted in The Rocky Horror Picture Show. Frank N. Furter doesn't really try to pass off as a woman yet Brad (ASSHOLE!) ends up falling for his seductive charm anyway.
  • Averted in Some Like It Hot. Jack Lemmon and Tony Curtis actually walked around the studio lot in drag in order to make sure they could realistically pass for female. The scene were they try using mirrors in the public ladies' room in order to fix their makeup is based on something they actually did while on the lot.
    • When asked why his "Josephine" was so much more feminine than Jack Lemmon's "Daphne", Tony Curtis explained that he was so scared to be playing a woman (or a man pretending to be one) that his tightly wound body language could be read as demure and shy, traditionally feminine traits, whereas Lemmon, who was completely unbothered, "ran out of his dressing room screaming like the Queen of the May," kept much more of his masculine body language.
  • Sorority Boys is a textbook example. Back to Roger Ebert:
    "What is unusual about "Sorority Boys" is how it caves in to the homophobia of the audience by not even trying to make its cross-dressing heroes look like halfway, even one-tenth-of-the-way, plausible girls. They look like college boys wearing cheap wigs and dresses they bought at Goodwill. They usually need a shave. One keeps his retro forward-thrusting sideburns and just combs a couple of locks of his wig forward to "cover" them. They look as feminine as the sailors wearing coconut brassieres in South Pacific."
  • In Taking Woodstock, Liev Schrieber plays Vetty von Vilma, a transvestite woman. In the part he's very muscular and has an apparent deep voice, in addition to very visible facial hair.
  • There was a short from The Three Stooges where Curly dressed like an Indian maiden and a mountain man fell in love with him. Guess it's been a really long time since he last saw a woman.
  • Averted by Dustin Hoffman in Tootsie. He might not be an attractive woman (a fact lampshaded several times in the film) but he at least looks like one. That Oscar nomination was well-deserved.
  • The failure—or prime source of comedy, depending on how you look at it—of White Chicks is generally considered to be a combination of this and disturbingly unconvincing makeup.
  • In Gentlemen of Fortune, the crooks end up escaping in drag. Not only it's incredibly conspicuous, one of the crooks still tries to hit after girls and tries to use the men's bathroom.
  • Averted with Zahara in Bad Education, who makes an effort to adopt feminine mannerisms, hair, and makeup on top of the women's clothing. And then played straight with the real Ignacio, who has stubble and an extremely deep voice.
  • Sherlock Holmes: A Game of Shadows had Holmes disguising himself as a woman. Since it was a last minute disguise, it wasn't one of the better ones.
  • At the climax of Mulan several of Mulan's male comrades join her in infiltrating the palace by disguising themselves as concubines. Yao doesn't even bother shaving his beard and one of Ling's breasts appears to be crooked, but Chien-Po is the most passable of the three. Amazingly the disguises work on some guards.

    Literature 
  • Averted/Lampshaded in Adventures of Huckleberry Finn. Huck goes into town disguised as a girl, but a woman he encounters immediately tells he's just a boy in disguise.
  • Hilariously played with in the Discworld novel Monstrous Regiment. Blouse takes the guise of a woman and is ridiculously bad at it, to the point where all the washerwomen notice right away but don't say anything because they think it's entertaining. But while the women aren't fooled by his awful, extremely stereotypical act, the male guards buy it completely. The funniest part is when the female soldiers masquerading as male soldiers decide to don women's clothing to also infiltrate enemy lines, they're immediately accused of being this trope, saying that they're obviously male and it's the worst attempt at drag they've ever seen.
  • Dave Barry's Only Travel Guide You Will Ever Need recommends that airline passengers who might fit the profile of a terrorist ("Sex: Male; Age: 15 to 74; Looks Suspicious: Yes") to draw away the attention of security personnel away by wearing a dress and "periodically remarking out loud to nobody in particular: 'I certainly have a lot of body hair, for a woman!'"

     Live Action TV  
  • Bosom Buddies ran on this trope.
  • Done on purpose in the short-lived series The Ugliest Girl in Town.
  • Conan wore pearls, lipstick and a wig to try to pass himself off as Callista Gingrich in Conan.
  • There was an episode of Jeeves and Wooster where Wooster goes undercover as a woman for some reason, and later in the episode Jeeves does. It was far-fetched, even compared to the usual events of the series.
  • Barney Miller - the detectives were assigned to disguise themselves in drag to catch criminals - Dietrich took to the job with good humor, but never realized he just looked like a big guy in a dress.
  • Like many British comedies, Doctor in the House and its sequel series featured many episodes of men dressing as ladies, and never looking believable doing it.
    • In "Doctor on the Box" from Doctor in the House, three medical students dress a fourth up as an elderly female patient to sabotage an interview as part of a documentary on the hospital; the fact that he is supposed to be an old woman does not stop him from squeezing the female interviewer's bottom. Chaos ensues when the subjects of the documentary discover the deception and decide to administer an enema, and then the real patient returns.
    • The Doctor in Charge episode "Mum's the Word" involves the board members having to choose between Dr. Waring and Dr. Bingham as a junior doctor representative on the board; Dr. Stuart-Clark claims that Waring's mother is a Countess (she is, in fact, a policeman's wife). As she is at the hospital as a patient, the board members decide to meet her, and Stuart-Clark dons a blonde wig, blue eyeshadow, and women's clothing and pretends to be Mrs. Waring while the real Mrs. Waring is kept out of sight. His disguise manages to charm the board members, and Waring gets the position on the board.
    • "A Turn for the Nurse" from Doctor on the Go sees Stuart-Clark trying to enter a ringer for a "best nurse" competition so that no-one need find out the prize money doesn't exist; Waring persuades her to drop out of the competition, and when Stuart-Clark finds out and reveals the "prize money" quandary, Waring has to dress up in drag as their entrant. His boss, Professor of Surgery Sir Geoffrey Loftus, recognises Waring immediately, but bites his tongue; meanwhile, rival hospital Highcross board member Sir Edmund Steele takes quite a liking to Waring...

    Mythology 
  • There is a Norse story in which Thor must disguise himself as Freya in order to trick the giants. The giants fall for every one of Loki's excuses about why "Freya" looks so haggard, has such a big appetite and can eat an entire cow, has a beard and can drink so much.

    Professional Wrestling 
  • Santino Marella's appearances as "his twin sister from Italy", Santina.
  • In 2003, thanks to a match stipulation, Stephanie McMahon had to engage in Hot Lesbian Action with another woman. Eric Bischoff said he found "the ugliest lesbian in the world" for her, but everyone (except Bischoff) knew the "lesbian" was Rikishi.
  • In Memphis in 1987, Jerry Lawler disguised himself as a female fan at ringside so he could get close to and attack Tommy Rich. In his book, Lawler said that outside of a little lipstick, they didn't put any makeup on him for it.
  • In the 1980's, Jimmy Valiant got Miss Atlanta Lively, "the toughest hooker in Atlanta", to be his tag team partner for a match. "Miss Atlanta Lively" was future NWA Champion Ronnie Garvin in a blond wig and a padded bra.

    Theatre 
  • Plump washerwomen take note, this is an absolute requirement for any Dame in any Pantomime! Never leave home without your ovious falsetto voice or bustle. Failure to produce bustle or react with extreme scepticism to cries of "they're behind you!" may lead to revoking of your 12x10 comedy-sized licence.
  • The character The Old Snatch in the musical Me and My Dick— there are other cross-dressing roles, but this one is played by a man with a gravelly voice and a beard.
  • The original stage version of Hairspray cast gravelly-voiced Harvey Fierstein as the mother, Edna Turnblad. The original movie and movie-musical also have the role played by a man, but they attempt to make the mother somewhat feminine and are not examples.

     Video Games  
  • In SNK Gals Fighters, Iori Yagami has disguised himself as "Miss X" by wearing a long-skirted Sailor Fuku and a mask (in true sukeban fashion) and insisting he's a girl. Nobody who sees him believes it.

    Web Animation 
  • Rapid Thunder (alias Codename: Albatross) in Mappy is a male corporate spy disguised as the female personal assistant of Nyamco CEO Goro. His whole disguise is literally a wig that isn't on right; he doesn't even affect a voice.

    Webcomics 

     Western Animation  
  • In an episode of Bob's Burgers, Bob makes friends with some fairly successful transvestite hookers, who look exactly like men in spandex dresses.
  • Hefty Smurf disguises himself as Smurfette (also not perfectly) in The Smurfs episode "Smurfette For A Day" to protect her from a gnome who wants to marry her.
  • In the "Black Friday" trilogy of South Park (and also in South Park: The Stick of Truth), Kenny dresses up as a princess... and still wears his parka underneath the whole thing, making it very conspicuous.


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