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* Played with in [[Family Compo]]: for Masahiko's entry ceremony, he asks his [[Cross Dresser|crossdressing]] [[Nephewism|aunt and uncle/adoptive parents]] to dress according to their biological sex. [http://www.mangafox.com/manga/family_compo/v01/c004/10.html The result] [[Hilarity Ensues|isn't what he expected]]. They look like genuine crossdressers, but are in fact Recursive Crossdressers.
* In ''[[Nononono]]'', Nono is a girl who pretends to be a boy to continue ski jumping. After she's caught in her underwear by the [[Alpha Bitch]] Kourogi but mistaken for a crossdresser, she's forced to be Lourogi's slave, including wearing a maid's outfit.
* [[Wholesome Crossdresser|Minoru]] in ''[[
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* This is the main concept of ''Connie and Carla''. The two ladies, a performing duo, witness a murder and go into hiding by pretending to be drag queens.
* In Polish film ''Poszukiwany, poszukiwana'' (''Man or Woman Wanted'', a title hard to translate into English) by Stanisław Bareja, the main character, an art historian, has to hide from the police, wrongly accused of stealing a (godawful) painting. Therefore he disguises himself as a woman and takes up a work as a daily help. At one time he accidentally shows up to be more competent in certain area than one of his employers, so the latter decides to make the former his consultant. But the consultant [[God Save Us From the Queen|should be a man, so that people treat him seriously]], so the main character has to change once again but gives up job shortly afterwards.
* In ''[[Victor
* In the final scene of ''[[The Birdcage]]'', the senator's wife and daughter must pretend to be drag queens to escape the drag club without being noticed.
* At the end of ''[[Mulan]]'', Mulan does this in order to fight [[Big Bad|Shan Yu]] and save China.
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* Similarly, there's a Black Lace "novel" about a young woman who wants to be an artist, so she disguises herself as a boy to enter the all-male art academy and is later picked to play a girl in a parade. Many, many interesting situations later she's no longer sure ''who'' she is.
* [[Discworld]]:
** In ''[[Discworld
** Likewise in ''[[Discworld
* In ''[[Tipping the Velvet]],'' Nancy is deemed not to make a good male impersonator because she looks too much like an actual boy (this makes perfect sense in a setting where the point of male-impersonation acts is to be daring and transgressive rather than completely realistic). She becomes much more successful when her male costume is modified to look a little more feminine.
* [[Marion Zimmer Bradley]]'s Lythande is a woman pretending to be a man, since women are not allowed to be Magi. At one point, she has to pose as a female dancer, prompting comments of how realistic the costume is.
* Naomi Kritzer's ''Turning the Storm'' features a lesbian disguised as a man who dresses up as a woman...and then gets hit on by a gay man.
* The YA novel ''Flipside'' begins with the members of a high school drama department discussing ''As You Like It'', a play listed below. The casting director decides to make it one level more recursive by casting a guy as Rosalind and a girl as Orlando. Then the guy turns out to [[Wholesome Crossdresser|like wearing a dress]], the girl turns out to [[Conveniently-Common Kink|like guys who wear dresses]], and things get really weird. (And no, this ''isn't'' porn.)
* Played with in ''[[Garrett
* In ''Cue for Treason'' by Geoffrey Trease, one of the main characters is a girl who disguises herself as a boy in order to become an Elizabethan-era actor, and naturally ends up playing all the female parts onstage.
* Referenced when discussing Shakespeare in ''[[Horrible Histories]]'', describing Elizabethan casting as "women pretending to be boys pretending to be women pretending to be boys."
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== [[Live Action TV]] ==
* In ''[[History Bites]]'', one episode has a fan of Shakespeare who dresses up as her favourite character. This means she's dressed as a boy, who was actually a woman, who is played by a man, while wearing her own clothes.
* A slight twist occurs in the ''[[
* In ''[[Blackadder Goes Forth]]'' the character Bob, a [[Sweet Polly Oliver]], steps in to replace a drag performer. {{spoiler|The General who had become [[Attractive Bent Gender|attracted to the previous drag performer]] refuses to believe that Bob is female and loudly criticises "That disgusting drag act." It's even funnier if the viewer is aware that [[Reality Subtext|Stephen Fry, who plays the General, is gay]].}}
* ''[[The Drew Carey Show]]'' sends up this trope in "Drew's Inheritance," centered on the [[Hilarity Ensues|wacky hijinx]] resulting from the [[On One Condition|eccentric will]] of the Careys' late eccentric television-and-movies-obsessed relative. His condition for Steve Carey-- a [[Wholesome Crossdresser|heterosexual cross-dresser]]-- receiving his share was to dress like a recursive crossdresser, with a male layer of deception on top. Wearing a suit for such a formal occasion, Steve remarks that he can just dress as he is, and the executor realizes that Uncle Cecil didn't think that one through very far.
* In the Japanese TV show ''[[Journey to
* In the Japanese drama remake of [[Hana Kimi]], during a talent show, Ashiya's clothes were stolen, so "he" could walk onto the stage [[Shirtless Scene|shirtless]]. Fortunately, the doctor (who knew who she was) came along and slipped her a dress, along with a wig. The audience, mainly guys, were stunned that the cute classmate of theirs made such a pretty girl. One of Ashiya's friends, a playboy, promptly got a nosebleed and mentally berated himself for having such thoughts towards a "guy".
* In a ''[[Wings (TV series)|Wings]]'' episode, Brian and Helen are stranded in New York with no money, and a drag contest seems to be the only way to finance their way home. They agree that Brian would never make a convincing enough woman to win, so they pretend that Helen is a transvestite male and enter her in the contest.
* ''[[Glee]]'' has a rather odd example. Although Kurt does not have the same clothes, in the "Duets" episode he does "Le Jazz Hot" from ''[[Victor
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'''Jesse''': Oh, you mean like that weird show we saw in Vegas?<br />
'''Joey''': You might want to stay away from Shakespeare. }}
* The play ''[[Victor
* Happens quite frequently in [[Opera]] -- particularly when a female singer plays a guy who dresses as a woman at some point.
** The most famous example is probably ''[[
** This variant occurs in ''[[The Phantom of the Opera]]'', with Christine playing the pageboy, who is dressed as a maid because he's having an affair with the lady of the house and wants to be discreet. In the (thankfully brief) scene we see of this opera, the husband is completely fooled and hitting on the 'maid'.
** Another famous operatic use of this trope is ''[[
* The [[Gilbert and Sullivan]] operetta ''[[Princess Ida]]'' has men all-too-ready to crossdress as women, in order to slip into the women's college, where most of the opera takes place. In Gilbert's original play, ''The Princess'', the men were played by women actresses, and after the recursive crossdressing, then spent most of the play dressed as women.
* In ''Moby Dick! The Musical'', the Headmistress in the framing device is played by a man in drag. She then crossdresses (and goes back into a tenor/baritone range) to play Captain Ahab.
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