->'''Ronnie Barker:''' You'll have to bear with me, because remember, I'm a woman playing a man who is playing a woman -- aren't I dear?
->'''Ronnie Corbett:''' Oh, at least.
-->-- ''Series/TheTwoRonnies'', as "Ball and Socket"

A character or actor disguises their gender. For some (frequently contrived) reason they then have to re-disguise it as their real gender. And then re-re-disguise as their fake gender, and so on until they collapse into a singularity of androgyny. Often, another character -- who may have been SweetOnPollyOliver -- will comment on [[YourCostumeNeedsWork how unconvincing the second act of crossdressing is]], revealing how completely he was fooled by the first.

Often this overlaps with PaperThinDisguise and WholesomeCrossdresser.

A SubTrope to GenuineImposter.


[[folder:Anime and Manga]]
* In ''LightNovel/BokuWaTomodachiGaSukunai'' there's [[spoiler: Yukimura Kusunoki - a girl who pretends to be a boy, but dresses like a girl in order to be more manly. She does not even know that she is female and is convinced that she is a boy, albeit a feminine one.]]
* In ''LightNovel/MayoChiki'' when Subaru is disguised as "his" female cousin Puniru, Usami is not convinced by the ''obvious'' disguise...even though Subaru is actually a girl who regularly pretends that she is a boy.
* ''Anime/RomeoXJuliet'': Juliet is a girl who has been raised as a boy for safety reasons, and everyone outside her closest circle thinks she's a boy. One of these people is her friend Emilia, who at the start of the series dresses her up as a girl... not knowing that she's invoking the trope.
* In the {{Manhwa}} ''LoveInTheMask'', Hyubin is a girl forced to be a boy because her boss claimed no one would take a female bodyguard seriously. In one of the few happy moments of her angst-filled life she gets to play Juliet in her school's traditionally gender-flipped performance of ''Romeo and Juliet''. Naturally, everyone comments on how "he" is the most beautiful and feminine Juliet ever.
* Touma & Mako-chan in ''Manga/MinamiKe''. Touma in particular has issues with this since some people around her (i.e. Atsuko) keep geting confused about what gender she actually is.
* ''Manga/PenguinRevolution'':
** Recursive Crossdressing becomes an ongoing issue for Yukari Fujimaru after she agrees to become Ryo Katsuragi's personal agent. Because Ryo's talent agency doesn't employ women as agents, Yukari is obliged to [[WholesomeCrossdresser pretend to be a man]] while acting as Ryo's agent, while at the same time she continues to attend high school as herself. Since she has nowhere else to live, she moves in with Ryo and his roommate Ayaori... who works for the same talent agency and attends the same high school. Yukari and Ryo get around this issue by telling Ayaori that, like Ryo himself, "Yutaka" has been instructed to [[WholesomeCrossdresser attend school disguised as a girl]]. Fortunately for both Ryo and Yukari, Ayaori's [[BlindWithoutEm eyesight is very poor]].
** A later chapter features an event hosted by the Peacock where the talent managers dress in drag, including Yukari.
* In ''Manga/PrincessKnight'', Sapphire must disguise "himself" with a blonde wig and gown to impersonate a girl when she wants to woo Prince Frank.
* Frequent in ''Manga/OuranHighSchoolHostClub'', with the subversion Haruhi Fujioka never actively ''tries'' to keep her gender a secret. The two reasons she doesn't tell anyone are 1. They didn't ask. 2. They enjoy their current preconceptions. The episode in which a secondary character discovers it is recommended.
** Invoked when female fangirls giggle about how much they'd like to see {{Bifauxnen}} Haruhi dressing in girls' clothing because "he" is so pretty.
** Haruhi is also dressed as a girl at one point for a Zuka Club production, and is ''really'' ridiculous-looking with strange ringlets and clown-like makeup that nearly descends into the UncannyValley. (though theatrical makeup is often exaggerated, it's never exaggerated ''that'' much) She's much more believably "disguised" as a girl in the episode with the obnoxious elementary school boy who wants to impress the girl he likes and the episode with the big ball where the club is trying to get the heir to the china company and his fiance together. In the former she just wears her old middle school SailorFuku, in the latter a ball gown and wig.
** She ''also'' dresses in 17th century French "drag" for a host club event, as seen [[http://static.tvtropes.org/pmwiki/pub/images/host_club_smaller.jpg here]].
** When the Host Club dresses in kimonos, Haruhi wears one designed for a woman. Her clients mention that she looks just like a girl in it.
* In ''Manga/RanmaOneHalf'', for the battle with [[HyperspaceArsenal Mousse]], Ranma, who is stuck in female form at the time, disguises herself as a guy (and faked a deep voice) and disguises herself ''further'' as a PlayboyBunny under the male disguise. All of this, just so everyone believes that the {{Stripperiffic}} [[MsFanservice female look]] was a disguise meant to humiliate Mousse and his magician-like "Hidden Weapons" style. The Fuurinkan school audience is indeed [[MaleGaze quite fooled]] that the ''male'' Ranma had disguised himself as a woman (even when she's [[ClothingDamage naked]]) who was disguised as a man. At least, until the "disguise" comes back and proves to be the real thing.
* A major part of Aikawa's teasing of Maki in ''Manga/PrunusGirl'' is the suggestion that he might actually be a girl claiming to be a guy dressed as a girl. Maki keeps his distance.
* In ''Manga/TokyoCrazyParadise'', the main character, who has been raised as a boy even though she is female, has to dress in women's clothing early on in the series, and feels like she is crossdressing. People who knew her and saw her would think she's in drag, even though she's (genetically) female.
* Played with in ''Manga/FamilyCompo'': for Masahiko's entry ceremony, he asks his {{transsexual}} [[NePhewism aunt and uncle/adoptive parents]] to dress according to their biological sex. [[http://www.anymanga.com/family-compo/001/004/010/ The result]] [[HilarityEnsues isn't what he expected]], since they look like genuine crossdressers, but are in fact Recursive Crossdressers.
* In ''Manga/{{Nononono}}'', Nono is a girl who pretends to be a boy to continue ski jumping. After she's caught in her underwear by the AlphaBitch Kourogi but mistaken for a crossdresser, she's forced to be Lourogi's slave, including wearing a maid's outfit.
* [[WholesomeCrossdresser Minoru]] in ''Manga/AKB49RenaiKinshiJourei'' claims to be working in a crossdressing café when he was caught by his senior in his normal male self. Luckily for him, she was convinced and was even impressed by the perfectness of his "disguise".
* Mikusa from ''Manga/ArataKangatari'' eventually has to cross-dress as her true biological sex [[spoiler:in order to infiltrate the location of Kugura's harem.]]
* Jun from ''Manga/NatsuNoArashi''.
* ''Manga/NozomuNozomi'' plays this trope all over the map. Tao Nozomu starts out as a barely pubescent middle school boy whose interest in [[WholesomeCrossdresser crossdressing]] somehow triggers an inexplicable GenderBender. Nozomu is so convincing as his "cousin" Nozomi that even his potential love interest doesn't recognize him. Even his little sister, who knows about the cross dressing but not about the GenderBender, is astounded at how girly "Nozomi" acts, not realizing that Nozomu ''is'' a (physical) girl pretending to be a boy dressed as a girl. Nozomu/Nozomi manages to hide his/her GenderBender for a full year as he/she undergoes female puberty and experiences all of the physical and mental changes that entails, to the point where Nozomu no longer knows if [[WholesomeCrossdresser he is boy who likes to dress as a girl in secret]] or [[SweetPollyOliver she is a girl who is forced to dress as a boy in public.]] Ultimately a school swim class and a crush on her male best friend force Nozomu's hand, as she is no longer androgynous enough physically or mentally to maintain the pretense.

[[folder:Comic Books]]
* ''Fashion Beast'' stars Doll Seguin, a woman with a manly frame and face and small breasts who dresses and carries herself like a drag queen. Her counterpart, "Tomboy", is a man who dresses and carries himself like, well, a tomboyish girl.
* In ''ComicBook/YTheLastMan'', the titular Yorick must conceal his gender for his own safety much of the time. At one point, he has let his beard grow out, encounters a female-to-male crossdresser, and has to pretend to be the same. He is treated to a particularly humiliating instance of YourCostumeNeedsWork.

[[folder:Films -- Animated]]
* At the end of ''Disney/{{Mulan}}'', Mulan and the rest of the squad disguise themselves as concubines to get into the Imperial Palace. Although Mulan's already been revealed as a woman and discarded her disguise by then, so technically she's just a woman disguised as a... different woman.
* Ursula of ''Disney/TheLittleMermaid'' is a meta example, as she is a female character based on a man dressed as a woman (namely the drag queen Divine).

[[folder:Films -- Live-Action]]
* AceVenturaPetDetective: One of the main characters is [[spoiler:a man disguised as a woman. But the character is actually played by a [[Creator/SeanYoung woman]] except for a flashback.]]
* ''Film/ShakespeareInLove'' features Lady Viola dressing as a boy to get a part in a play, and she manages to get the part of Romeo, [[spoiler:only leaving after being ratted out by Tilney and John Webster. In the end, she has to play Juliet after the boy actor's voice broke, with Will, Henslowe, and everyone present when Tilney outed her having to play along, and the rest believing she is just that good. Tilney isn't fooled, though, and it's only through Queen Elizabeth's intervention that they get away with it.]]
* ''Film/MissCongeniality 2'': Near the end, two female agents have to pretend to be drag queens and one reminds the other, "[[Film/VictorVictoria Just remember that you're a woman pretending to be a man pretending to be a woman.]]"
* In the stoning scene near the beginning of ''Film/MontyPythonsLifeOfBrian'', many of the actors are men, who are playing women, who are disguising themselves as men ([[GirlsWithMoustaches badly]]) so they can participate in stonings. Except that some of the actors are actually women passing off as male actors doing the above, since Monty Python had made such a tradition of comic crossdressing.
* 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 a certain area than one of his employers, so the latter decides to make the former his consultant. But the consultant [[GodSaveUsFromTheQueen should be a man, so that people treat him seriously]], so the main character has to change once again but gives up the job shortly afterwards.
* In ''Film/VictorVictoria'', Julie Andrews plays a woman who masquerades as a man who works as a drag queen. The film was later adapted for Broadway (see Theater, below), and is itself an adaptation of a 1933 German film, ''Viktor und Viktoria''.
** The 1935 English film ''First a Girl'' works on the same premise.
* In the final scene of ''Film/TheBirdcage'', the senator's wife and daughter (along with the "conventionally crossdressed" senator himself) must pretend to be drag queens to escape the drag club without being noticed.
* ''Film/{{Transamerica}}'', like many works where a non-TG actress plays a TG character, provides an example from the perspective of RealLife. Actress Felicity Huffman plays Bree, a male-to-female {{Transsexual}}. Thus, a biologically female actress is playing a biologically male character who has the typical appearance of a woman.
* Discussed on the DVD commentary for ''Film/HedwigAndTheAngryInch''. A deleted scene shows Yitzhak's back story. Yitzhak, in both the film and the stage show, is played by a woman. Yitzhak also wants to be a drag queen. During the deleted scene in the film, you have Hedwig--a transwoman played by a gay man--and Yitzhak kissing. Yitzhak is played by a straight woman pretending to be a man who wants to be a woman (and comes out in drag at the end of the show). You could get lost in the number of genders in that one scene, but that's what Hedwig is all about.

* In Creator/TadWilliams' novel ''Shadowplay'', the exiled Princess Briony disguises herself as a boy and takes refuge with an all-male theater company, who convince her to play the female lead in their new play. Most of the actors quickly figure out that she's a girl, but keep her secret for as long as she remains with them.
* 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.
* Literature/{{Discworld}}:
** In ''Discworld/MonstrousRegiment'', protagonist Polly Perks [[spoiler: (along with her fellow women-disguised-as-men from the squad)]] dresses up as a washerwoman to sneak into an occupied fortress. Which, as she points out, means she's a woman disguised as a man disguised as a woman. True to the trope, their "disguise" as women is immediately caught when they try to enter, and one of their number [[spoiler:(who is with child) winds up having to prove her gender in the most obvious way possible. Meanwhile, the one actual man who disguised himself as a woman gets in without a hitch]], which irks Polly to no end. This is even more convoluted at the end, when [[spoiler: the entire squad is discovered to be actually female, brought up on charges for dressing like men, which is illegal, and their lawyers point out they are actually dressed as women at the time.]] Polly turns down an offer of male clothing because "Then I'd be a woman dressed as a man dressed as a woman dressed as a man," which would be too confusing even for ''this'' book.
** Likewise in ''Discworld/TheLastContinent'' there is a woman who filled in for her brother in his friends' drag act after a nasty surfboarding accident, but after her fellow drag queens get into yet another fight, she decides "Being a female impersonator is no job for a woman."
* In ''Literature/TippingTheVelvet,'' Nancy is deemed not to make a good male impersonator because she looks too much like an actual boy (this makes perfect sense in context, as the point of male-impersonation acts is to be transgressive rather than convincing). She becomes much more successful when her male costume is modified to look a little more feminine.
* Creator/MarionZimmerBradley's Literature/{{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.
** In another story Lythande ends up cursed with possession of an magical item which only tolerates a female owner and can only covertly dispose of it by infiltrating a stronghold which only admits women. In this instance trying to pass as female (given the terrible risk of simply being identified as female) is treated as a very uncomfortable and nervous business rather than a source for comedy.
* ''[[Literature/FiresOfTheFaithful 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 [[WholesomeCrossdresser like wearing a dress]], the girl turns out to [[ConvenientlyCommonKink like guys who wear dresses]], and things get really weird. (And no, this ''isn't'' porn.)
* Played with in ''[[Literature/GarrettPI Deadly Quicksilver Lies]]'', in which [[spoiler: the drag-queen villain is reputed to have posed as a call girl and had assignations with unsuspecting men in his feminine guise. It's eventually revealed that the villain is ''genuinely'' female, who'd created a sadistic crossdresser persona to pose as her own pimp, rather than be bullied into working for a real one]].
* 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 ''Literature/HorribleHistories'', describing Elizabethan casting as "women pretending to be boys pretending to be women pretending to be boys."
* In the world of ''Literature/ABrothersPrice'', female whores try to look as masculine as possible. A rare male character briefly disguises himself as one, wearing makeup and a feather boa to hide his man's apple.
* Suggested towards the tail-end of one of the ''Literature/{{Leviathan}}'' series's [[SweetPollyOliver character arcs]]: Deryn Sharp, daring British soldier and secret girl, accepts [[spoiler: a job as a hush-hush British spy]]. It's suggested that she, while still impersonating a boy in her larger life, would perhaps have to disguise herself as a woman on some missions. It's twisted even farther in a bonus chapter, in which her [[spoiler: [[SweetOnPollyOliver love interest]], Prince Alek of Hohenburg, himself wears a dress to a costume party after trying to get Deryn, who still lives as a boy, to go to the party in one.)]]
* Happens to Lieutenant Winter Ihernglass (a classic SweetPollyOliver) in the second book of ''Literature/TheShadowCampaigns.'' Winter's CO, who is in on the secret of her true gender, orders her to infiltrate The Leathernecks, an infamous all-female organized crime outfit in Vordan City. Winter amusedly comments that she's really a girl passing as a guy who's going undercover as a girl. The twist goes even further once she actually ''does'' contact The Leathernecks, as it turns out that the entire gang knows of her gender-bending exploits, thanks to the gang's leader, who turns out to be an OldFlame. She even gets a classic YourCostumeNeedsWork from one of her other superiors who isn't in on the secret and is surprised that such a 'bad' disguise fooled anyone.

[[folder:Live Action TV]]
* In ''Series/HistoryBites'', 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 ''Series/StarTrekTheNextGeneration'' episode "The Outcast": an actress plays an androgynous alien reveals that it ''actually'' leans female in order to act on its attraction for Commander Riker. [[DoesThisRemindYouOfAnything She/it has had to cover this up all its/her life because of a societal taboo against gender identity, which is seen as unnatural and officially classified as a mental illness]].
** Jonathan Frakes, the actor playing Riker, apparently lobbied beforehand to have the female-identifying alien played by a male actor (which would add ''another'' layer of this trope), in order to heighten the social commentary by playing with the audience's own sense of the taboo involved.
* In ''Series/{{Blackadder}} Goes Forth'' the character Bob, a SweetPollyOliver, steps in to replace a drag performer. [[spoiler: The soldiers love it, but General Melchett who had become [[AttractiveBentGender 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 [[RealitySubtext Stephen Fry, who plays the General, is gay]].]]
* ''Series/TheDrewCareyShow'' sends up this trope in "Drew's Inheritance," centered on the [[HilarityEnsues wacky hijinx]] resulting from the [[OnOneCondition eccentric will]] of the Careys' late eccentric television-and-movies-obsessed relative. His condition for Steve Carey-- a [[WholesomeCrossdresser 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 ''{{Series/Monkey}}'', the male Buddhist monk Tripitaka is [[CrosscastRole played]] by a female actor (Masako Natsume). In one episode, Monkey disguises Tripitaka as a woman, so that he can be sneaked through the Land Of Nightmares. Crossdressed Tripitaka is so beautiful that both the lustful Pigsy, and the King of the Land of Nightmares become infatuated with him. HilarityEnsues.
* In the Japanese drama remake of ''Manga/HanaKimi'', during a talent show, Ashiya's clothes were stolen, so "he" could walk onto the stage {{shirtless|Scene}}. 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 ''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.
* ''Series/{{Glee}}'' has a rather odd example. Although Kurt does not have the same clothes, in the "Duets" episode he does "Le Jazz Hot" from ''[[Film/VictorVictoria Victor/Victoria]]''. This makes him a man paying homage to a woman dressed as a man dressed as a woman.
* ''Series/{{Degrassi}}'''s [[http://www.youtube.com/watch?v=88BlhSp5wig Stuff Clare Says]] video features actress Jordan Todosey playing a [[{{Transsexual}} transgender]] boy (Adam), playing a girl ("Clare").
* In the ''Series/{{Leonardo}}'' episode "Diabolical Acts", the SweetPollyOliver Lisa/Tomaso auditions for a play. Leo advises her not to take a female role, because "You can't be a girl playing a boy playing a girl. It's too confusing". In the end, she's the female lead, although the actor-manager thinks Leo would be [[YourCostumeNeedsWork much better in the role]].
* This has happened on ''Series/RuPaulsDragRace'' a few times:
** In Season 1's makeover challenge where the DragQueen contestants had to give glamorous makeovers to {{Tomboy}} martial artists, Ongina and her partner do a prom king and queen look, with Ongina as the "king".
** In a Season 4 runway, Milan came out in a Music/JanelleMonae-inspired tuxedo. Monae is known for her dapper androgynous suits.
** In Season 5's SubvertedKidsShow challenge, Alaska became "Buffalo Bill", a male farmer, to the judges' confusion. Whereas Milan was at least still impersonating a woman in the above example, Alaska was simply a man in overalls.
** In a Season 6 runway where the queens had to pay homage to one of [=RuPaul=]'s outfits, Milk came out as "Workroom Ru", when Ru interacts with the queens as his normal male self. This became one of Milk's most memorable and (among the other queens) controversial moments.
** In the OnceASeason "Snatch Game" challenge where the queens impersonate celebrities for a ''Series/MatchGame'' parody, a few have portrayed other drag queens, but Season 7's Kennedy Davenport was the first to straight-up play a man: Little Richard. But due to Richard's flamboyant style of dress and AmbiguouslyGay mannerisms, it basically ''was'' a drag performance, and Kennedy won the challenge for both thinking outside the box and actually making it funny.

* Classical Athenian comedy was probably the place where this trope originated, since all the actors in the Athenian theatre were men. The most prominent example is Creator/{{Aristophanes}}' Ekklesiazusae ("Women of the Citizen Assembly"), which features a variety of cross-dressing and gender-based humour. In this play the women of Athens (played by male actors) wear false beards and pretend to be men in order to vote themselves into political franchise.
* Practically every Creator/WilliamShakespeare comedy, as originally performed, has boy actors playing women who disguise themselves as boys.
** ''Theatre/AsYouLikeIt'' goes even further: the female lead (Rosalind) disguises herself as a boy (Ganymede) who is then asked by Rosalind's lover Orlando to pretend to be Rosalind so he can practice courting her. Certain modern productions can be even worse. The epilogue to ''As You Like It'' is nominally spoken by Rosalind, but actually by the boy playing her (it contains the line "If I were a woman..."). Thus, if Rosalind is played by an actress and the epilogue included, we have: a modern actress playing a Shakespearean boy actor playing a woman disguised as a boy who pretends to be a woman (for ''five'' levels of recursivity).
** Lampshaded when explained on an episode of ''Series/FullHouse''.
-->'''Joey''': In all the original stage productions, the women's parts were actually played by men.
-->'''Jesse''': Oh, you mean like that weird show we saw in Vegas?
-->'''Joey''': You might want to stay away from Shakespeare.
** Also Lampshaded in John Troutman's notes, when ''Webcomic/LitBrick'' did an adaptation of ''TwelfthNight''.
** Portia from Theatre/TheMerchantOfVenice does this in the climax. As written, much of the humor of the scene is with regards to the actor playing Portia is a man, pretending to be a woman, pretending to be a man. Its especially noted in because Portia is regarded as one of the most positive female characters in Shakespeare's works, and is to female Thespians what playing Hamlet is to male Thespians. A male playing the role of Portia as written is unheard of in modern theater.
--> I suspect that Viola’s disguise would probably be better in a real life production of this play. Hell, in the 1600s, they would’ve just had to take the fake boobs off their actor.
* The play ''Theatre/VictorVictoria'', an adaptation of the original film (see above), is about this. A down-on-her-luck opera singer named Victoria (Julie Andrews in the film) can't find work, so a recent acquaintance and homosexual talent agent convinces her to pretend to be Victor, a drag queen who presents himself as a woman named Victoria. A confused mobster falls in love with her/him/her.
* Happens quite frequently in {{Opera}} -- usually a female singer plays a guy who dresses as a woman at some point.
** The most famous example is probably Cherubino from ''Theatre/TheMarriageOfFigaro'', which was written just late enough that this sort of role would go to a woman rather than a castrato.
** Another famous operatic use of this trope is ''Theatre/DerRosenkavalier'', where the teenaged Octavian disguises himself as the maid Mariandel and fools the Baron completely.
** In the comic opera ''Der Wildschutz'', a traveling noblewoman disguises herself as a young man ([[SweetPollyOliver it's safer]]). When she arrives in a village, they prevail on "him" to disguise himself as a woman and visit the local (notoriously lecherous) baron's castle. The villagers think it's hilarious that the baron is trying to seduce a boy--and are horrified when the baron's wife, to protect the innocent "girl", insists on sharing her own bed with her.
* This variant occurs in ''ThePhantomOfTheOpera'', 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'.
* The Creator/GilbertAndSullivan operetta ''Theatre/PrincessIda'' 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.
* ''[[http://www.youtube.com/watch?v=Cy6jgch8IVI The Friend Who Dressed]]'' takes this to a ridiculous level, culminating in the main character being [[spoiler:a boy disguised as a girl disguised as a boy disguised as a ''[[PaperThinDisguise dog]]''.]]
* This trope was very common in Spanish classic theatre (contemporary of Sir William), notably in Lope de Vega and Calderón de la Barca plays. Calderón's ''La Dama del Aire'' is possibly the best example.
* Subverted in Ben Jonson's ''Epicene, or The Silent Woman,'' in which the title character [[spoiler: is revealed to be a boy disguised as a woman. It's a subversion because, as a Jacobean play, all the female roles would have been played by boys, so revealing that a character played by a cross-dressed boy actually ''was'' a cross-dressed boy would have been quite surprising.]]

[[folder:Video Games]]
* In ''VideoGame/JadeEmpire'', this is noted by one playwright to be rather common in the acting industry, as women are technically barred from being actresses, but nobody cares to enforce it. Which is an interesting take on this trope, as it's noted that these scenarios typically involve the actual costumes being worn recursively, leading to the actress playing the female role ''actually being'' unconvincing. Weirdly, this seems to be the only instance of institutionalized gender restrictions in the game world. Women can be soldiers, philosophers, and [[spoiler:Emperors]] (if you go for the good ending) but not actors for some reason.
* In ''LightNovel/EienNoFilena'' or ''Eternal Filena'', the princess of the fallen kingdom of Filosera is raised and dressed as a man to protect her identity. During the game, she has to sneak away with an all female dance troupe which involves her assuming a female disguise over her male one.
* In ''VideoGame/QueenAtArms'', Prince Alastor throws a morale-boosting masquerade ball for the soldiers in his father's army. Being the quirky sort, he plans for it to be a {{crossdressing}} event, with the men in dresses and the (few) women in trousers. The trope comes in with protagonist Marcus, who is a SweetPollyOliver; she has to pretend to be a man pretending to be a woman.

[[folder:Visual Novels]]
* Chris in ''VisualNovel/PrincessWaltz'' is a girl who dresses like the boy she intends to become. At one point she is forced to dress like a female cheerleader by the rest of her class. The main character expects Chris to be angered by this (as she normally blows her top when treated like a girl), but Chris explains she doesn't care that much because she's being treated like a cross-dressing boy.
* The PlayerCharacter from ''[[VisualNovel/ShallWeDateNinjaShadow Shall We Date: Ninja Shadow]]'' is a {{bifauxnen}} who goes the SweetPollyOliver way to [[DeadPersonImpersonation impersonate her]] [[DudeLooksLikeALady dead brother]], and in all the routes she actually ''has'' to dress up as a woman so she can gather info in the local RedLightDistrict.

* Averted in ''Webcomic/NoNeedForBushido'', when the main characters must substitute for kabuki actors. Ina is specifically told not to play the female lead, because she wouldn't be convincing as a man playing a female role.

[[folder:Western Animation]]
* Perhaps the most extreme example on this page: In one episode, the main character of ''WesternAnimation/XavierRenegadeAngel'' disguises himself as a businessman disguised as a woman disguised as a man disguised as a SassyBlackWoman disguised as a business man disguised as [[ForHalloweenIAmGoingasMyself himself]]. And this is all in an attempt for him to become normal.

[[folder:Real Life]]
* According to Harpo Marx, the Creator/MarxBrothers once did a vaudeville tour with a woman pretending to be a drag queen.
* Sarah Edmonds was a SweetPollyOliver who enlisted with the Union army during the American Civil War. She spent most of the war working for the intelligence division behind enemy lines, in various -- mostly female -- disguises.
* [[CosplayCafe A café in Tokyo]] features female staff dressed as young men in maid costumes. It caters to the [[YaoiFangirl fujoshi crowd]].
* If the Creator/WilliamShakespeare example above was not bad enough there are more than a few recorded instances of women dressing up as men to become actors, possibly adding an extra layer of cross-dressing to an already heavily cross-dressed plot.
* Then there's the 'biologically-challenged' drag queens or [[http://en.wikipedia.org/wiki/Faux_queen faux queens]], women who purposefully adopt the mannerisms of drag queens - in music, [[ScissorSisters Ana Matronic]] presents herself this way, as did Music/LadyGaga in her first few months in the spotlight.
* A controversial theory about UsefulNotes/JoanOfArc states that "she" was actually a man disguised as a woman. Who then wore male clothes and armour on the battlefield.



...''Confused'' doesn't even ''begin'' to describe how I feel now...