Recursive Crossdressing

Ronnie Barker: You'll have to bear with me, because remember, I'm a woman playing a man who is playing a woman.
Ronnie Corbett: Oh, at least.

— The Two Ronnies, "Ball and Socket"

A character or actor disguises their gender. For some (frequently contrived) reason they then have to re-disguise themself 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 Sweet on Polly Oliver — will comment on how unconvincing the second act of crossdressing is, revealing how completely he was fooled by the first.

Often this overlaps with Paper-Thin Disguise and Wholesome Crossdresser.

A Sub-Trope to Genuine Imposter.

Examples:

open/close all folders

Anime and Manga

Minoru in AKB49 – Renai Kinshi Jourei 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 Arata: The Legend eventually has to cross-dress as her true sex in order to infiltrate the location of Kugura's harem.
Crossplay Love: Otaku x Punk: The Maid Cafe Hana works at has a genderswap-themed day, so Hana ends up being a guy dressed as a girl dressed as a guy.
Touma & Mako-chan in Minami-ke. Touma in particular has issues with this since some people around her (i.e. Atsuko) keep geting confused about what gender she actually is.
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 Kourogi's slave, including wearing a maid's outfit.
Nozomu Nozomi plays this trope all over the map. Tao Nozomu starts out as a barely pubescent middle school boy whose interest in crossdressing somehow triggers an inexplicable Gender Bender. 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 Gender Bender, 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 Gender Bender 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 he is boy who likes to dress as a girl in secret or 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.
Frequent in Ouran High School Host Club, 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 Uncanny Valley Makeup. (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 Sailor Fuku, in the latter a ball gown and wig.
- She also dresses in 17th century French "drag" for a host club event, as seen 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.
Penguin Revolution:
- 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 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 attend school disguised as a girl. Fortunately for both Ryo and Yukari, Ayaori's eyesight is very poor.
- A later chapter features an event hosted by the Peacock where the talent managers dress in drag, including Yukari.
In Princess Knight, Sapphire must disguise "himself" with a blonde wig and gown to impersonate a girl when she wants to woo Prince Frank.
A major part of Aikawa's teasing of Maki in Prunus Girl is the suggestion that he might actually be a girl claiming to be a guy dressed as a girl. Maki keeps his distance.
In Ranma ½, for the battle with 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 Playboy Bunny under the male disguise. All of this, just so everyone believes that the Stripperiffic female look was a disguise meant to humiliate Mousse and his magician-like "Hidden Weapons" style. The Fuurinkan school audience is indeed quite fooled that the male Ranma had disguised himself as a woman (even when she's naked) who was disguised as a man. At least, until the "disguise" comes back and proves to be the real thing.
Romeo × Juliet: 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.
Spill it, Cocktail Knights! has a chapter where the crossdressing girl dresses back as a girl to give her male friends Valentine's chocolate so they don't feel bad for not getting any from girls. They accept it in the spirit in which it's given, but tell her that her she wouldn't be mistaken for a boy.
In Tokyo Crazy Paradise, 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.

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.
Played for Laughs in Kerry Kross: the titular detective (an attractive woman with a slightly mannish face) at one point has to infiltrate a party and puts on an evening dress with a fancy wig, but accidentally shows the I.D. card of a male friend of hers to the butler. When questioned on this, she "admits" she's a transvestite, much to the butler's embarrassment.
In Y: The Last Man, 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 Your Costume Needs Work.

Fan Works

The Rigel Black Chronicles: Harriet is attending Hogwarts under her pureblooded cousin Arcturus' name, but while there, she helps the Weasley Twins move an "elf on a shelf" around the school, making people laugh. To hide it in the girls' bathroom, she dresses as a girl — and gets caught by Professor Lockhart while leaving the bathroom. He doesn't see through her disguise, but Professor Snape does, with some amusing Dramatic Irony as he threatens to expel "Rigel" if he ever finds out "he" has been in the girls' bathroom again.

Films — Animated

Ursula of The Little Mermaid is a meta example, as she is a female character based on a man dressed as a woman (namely the drag queen Divine).
At the end of 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.

Films — Live-Action

Ace Ventura: Pet Detective: One of the main characters is a man disguised as a woman. But the character is actually played by a woman except for a flashback.
In the final scene of The Birdcage, 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.
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.
Discussed on the DVD commentary for Hedwig and the Angry Inch. 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.
Miss Congeniality 2: Armed and Fabulous: Near the end, two female agents have to pretend to be drag queens and one reminds the other, "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 Monty Python's Life of Brian, many of the actors are men, who are playing women, who are disguising themselves as men (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.
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 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.
The Taiwanese film 99 Cycling Swords has its protagonist, a female martial artist, taking on the guise of a man for most of the film. She did un-disguise back to a female when posing as her "sister" at one point in the film.
In Revenge of the Pink Panther, Clousseau is carjacked by a woman who turns out to be a transvestite, Claude Russo, who steals Clousseau's clothes (while leaving Clousseau with his dress) and is killed in his place shortly afterwards. Russo is played by actress Sue Lloyd, dubbed over by a male actor as soon as Russo reveals himself to be a man.
Shakespeare in Love features Lady Viola dressing as a boy to get a part in a play, and she manages to get the part of Romeo, 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.
In Tomboy, tomboy Laure pretends to be a boy. At one point her unwitting friend and Puppy Love object Lisa puts girly makeup on her noting how great "he" looks as a girl.
In Victor/Victoria, 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.

Literature

In Eien no Filena 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.
Coral in Undefeated Bahamut Chronicle needs to dress as a girl when tailing someone in a different country and later when she's made to act as Lux's bodyguard (in the latter case, to appear less threatening to potential attackers).
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.
A poem included in Ronnie Barker's compendium of old-fashioned bawdy humour Sauce! begins:
Two brothers started up a brother act,
But brother acts were a penny for ten.
So they started up a sister act instead,
But dressed themselves as smart young men.
In the world of A Brother's Price, 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.
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.
Played with in Deadly Quicksilver Lies, in which 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.
Discworld:
- In Monstrous Regiment, protagonist Polly Perks (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 (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 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.
- In The Last Continent 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."
The YA novel The Flip Side by Andrew Matthews 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 like wearing a dress, the girl turns out to like guys who wear dresses, and things get really weird. (And no, this isn't porn.)
In Haganai there's 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.
Referenced when discussing Shakespeare in Horrible Histories, describing Elizabethan casting as "women pretending to be boys pretending to be women pretending to be boys."
Suggested towards the tail-end of one of the Leviathan series's character arcs: Deryn Sharp, daring British soldier and secret girl, accepts 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 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.)
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.
- 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.
In Mademoiselle de Maupin by Théophile Gautier, Théodore is a Sweet Polly Oliver who plays Rosalind in a production of Shakespeare's As You Like It, adding yet another layer to a role which already involves Recursive Crossdressing.
In Mayo Chiki!, 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.
Happens to Lieutenant Winter Ihernglass (a classic Sweet Polly Oliver) in the second book of The Shadow Campaigns. 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 Old Flame. She even gets a classic Your Costume Needs Work from one of her other superiors who isn't in on the secret and is surprised that such a 'bad' disguise fooled anyone.
In Tad Williams' 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.
Sixes Wild: One of the few times Six willingly wears a dress is at a Stag Dance where she's passing as a guy in drag.
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 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.
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.
In The Shakespeare Stealer, one of the apprentices in Shakespeare's troupe is revealed to be a girl. Since the apprentices were prepubescent boys whose primary purpose in the troupe was to play female roles, she had been playing almost exclusively female roles onstage (the only one directly referenced is Ophelia, but there were unquestionably others). Adding to the layers, given Shakespeare's propensity for having female characters dress as men, it's likely that the girl in question, while posing as a boy, played a girl masquerading as a boy at least once.

Live Action TV

In Blackadder Goes Forth the character Bob, a Sweet Polly Oliver, steps in to replace a drag performer. The soldiers love it, but General Melchett who had become 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 Stephen Fry, who plays the General, is gay.
Degrassi: The Next Generation's Stuff Clare Says video features actress Jordan Todosey playing a transgender boy (Adam), playing a girl ("Clare").
The Drew Carey Show sends up this trope in "Drew's Inheritance," centered on the wacky hijinx resulting from the eccentric will of the Careys' late eccentric television-and-movies-obsessed relative. His condition for Steve Carey— a 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.
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/Victoria. This makes him a man paying homage to a woman dressed as a man dressed as a woman.
- When the theater club puts on a play of The Rocky Horror Picture Show, there's a lot of shuffling on who will play Dr. Frank N. Furter. Kurt flat out refuses to do it, and Mike is cast but then drops out because his parents don't want him to play a transvestite, so ultimately Mercedes is cast. Giving us a woman singing a song about being a drag queen.
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. 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 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.
In the Leonardo episode "Diabolical Acts", the Sweet Polly Oliver 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 much better in the role.
In the Japanese TV show Monkey, the male Buddhist monk Tripitaka is 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. Hilarity Ensues.
This has happened on RuPaul's Drag Race a few times:
- In Season 1's makeover challenge where the Drag Queen 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 Janelle Monáe-inspired tuxedo. Monae is known for her dapper androgynous suits.
- In Season 5's Subverted Kids' Show 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 Once a Season "Snatch Game" challenge where the queens impersonate celebrities for a Match Game 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 Ambiguously Gay mannerisms, it basically was a drag performance, and Kennedy won the challenge for both thinking outside the box and actually making it funny.
- Kennedy's performance has led to more male celebrities being impersonated, with the following seasons seeing Thorgy Thor as Michael Jackson, BenDeLaCreme as Paul Lynde, and Nina West as Harvey Fierstein, but like Little Richard, all three are flamboyant enough to still make it drag-like. The first UK season however saw two straight male celebrities, neither of whom are known for being campy and flamboyant: The Vivienne as Donald Trump, and Sum Ting Wong as Sir David Attenborough. Interestingly enough, the former was one of the winners, while the latter was eliminated.
A slight twist occurs in the Star Trek: The Next Generation 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. 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.^note
In a 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.

Manhwa

In Love In The Mask, 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.

Theatre

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.
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 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.
Subverted in Ben Jonson's Epicene, or The Silent Woman, in which the title character 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.
The Friend Who Dressed takes this to a ridiculous level, culminating in the main character being a boy disguised as a girl disguised as a boy disguised as a dog.
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.
Practically every William Shakespeare comedy, as originally performed, has boy actors playing women who disguise themselves as boys.
- As You Like It 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 Full House.
  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 Jodie Troutman's notes, when Lit Brick did an adaptation of Twelfth Night.
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.
- Portia from The Merchant of Venice 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.
The play Victor/Victoria, 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 The Marriage of Figaro, 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 Der Rosenkavalier, where the teenaged Octavian disguises himself as the maid Mariandel and fools the Baron completely. This is particularly interesting, since, for comedic purposes, the Mariandel-disguise has to be less than convincing. So you not only have a woman playing a man playing a woman, you have a woman playing a man playing an unconvincing woman.
- In the comic opera Der Wildschutz, a traveling noblewoman disguises herself as a young man (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.
The Phantom of the Opera: This variant occurs in Il Muto, with Christine playing the pageboy, who is dressed as a maid because he's having an affair with the lady of the house (played by Carlotta) 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 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.
Prince Kaguya: Kaguya, who was raised as a girl, has to disguise himself as a man at one point.
The Takarazuka Revue is an all-women musical theatre company. Their actresses are primarily divided into otokoyaku (male role actress) and musumeyaku (female role actress). However, some women can be played by otokoyaku for these reasons:
- The character is The Vamp, an older woman with a seasoned air, or villainous in general: the seductive Jaqueline in Me And My Girl, Lady of Black Magic Rosalia Condulmer in Casanova and Morgane in La Légende du Roi Arthur, etc. It's rare for musumeyaku to play a straight-up villainous character, as they are stereotyped as pure, if not heroic.
- One of the Revue's signature productions, The Rose of Versailles has Lady Oscar Francois de Jarjayes, a woman raised as a man. Lady Oscar is always played by otokoyaku, women trained to play assigned-male-at-birth roles. When it's an Oscar/André-centric musical, Oscar will be played by a top star (the lead otokoyaku of the troupe), because she's the main character, and it's expected that only top stars have the experience and talent required to walk the delicate line of gender presentation.
- Top musumeyaku Reika Manaki played Louis XIV in All For One, who is actually Louis' twin Louise, raised as a boy. She disguises herself as Louise and meets d'Artagnan outside of the palace, who remains unaware of her identity as the king during their encounter.

Video Games

In Jade Empire, 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 Emperors (if you go for the good ending) but not actors for some reason.
In Queen at Arms, 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 Sweet Polly Oliver; she has to pretend to be a man pretending to be a woman.
Umineko: Golden Fantasia has an example only noticable if you've played the original VN. In Jessica and Kanon's ending, the former forces the latter into cosplaying the Reimu to her Marissa. Keep count now - Sayo Yasuda is heavily implied to have been born male, but was assigned female after an accident damaged their genitals. Upon learning of this, they created the Kanon persona to see if life as a boy would suit them better, and now Kanon is cosplaying a female character. That has to be some kind of record.

Visual Novels

Chris in Princess Waltz 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 Player Character from Shall We Date?: Ninja Shadow is a bifauxnen who goes the Sweet Polly Oliver way to impersonate her dead brother, and in all the routes she actually has to dress up as a woman so she can gather info in the local Red Light District.

Webcomics

Averted in No Need for Bushido, 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.
xkcd has one non-gender example with convention of furries pretending to be humans.

Web Video

Contrapoints: Lampshaded in "The Aesthetic".
Natalie: People think I'm a man dressed as a women. But I'm actually a women who used to be a man, dressed as a man dressed as a women. Illusions~.
In Philosophy Tube's video "Antisemitism: An Analysis", Abigail (who had started her transition at this point but was still presenting as male online) plays Mademoiselle Y, a member of the French resistance and Author Avatar. To recap, Abigail is a transgender woman, pretending to be a man, who cross-dresses to play a woman.

Western Animation

The SheZow episode "Coldfinger" has SheZow - who is actually the male Guy Hamdon dressed as a female superheroine - dressing up as an ice cream man (complete with fake mustache) to fool Coldfinger into eating ice cream with spicy chips in it.
Perhaps the most extreme example on this page: In one episode, the main character of Xavier: Renegade Angel disguises himself as a businessman disguised as a woman disguised as a man disguised as a Sassy Black Woman disguised as a business man disguised as himself. And this is all in an attempt for him to become normal.

Real Life

According to Harpo Marx, the Marx Brothers once did a vaudeville tour with a woman pretending to be a drag queen.
Sarah Edmonds was a Sweet Polly Oliver 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.
A café in Tokyo features female staff dressed as young men in maid costumes. It caters to the fujoshi crowd.
If the William Shakespeare 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.
As one might expect, drag queens are very familiar with this trope:
- There are plenty of cisgender women who perform as drag queens. In music, Ana Matronic wore exaggerated makeup, as did Lady Gaga in her first few years in the spotlight.
- It's not uncommon for male drag queens to impersonate male artists for a single performance, particularly if the male artist is known for having a larger-than-life stage persona that blurs gender lines in his own way. Boy George, Prince, and David Bowie are perennial favorites.
- Many closeted trans people—who feel forced to pretend to be the gender they were assigned at birth—express themselves via drag, crossplay and other such activities which involve "impersonating" a member of their actual gender, if for whatever reason a full-time transition isn't a viable option for them.
A controversial theory about Joan of Arc states that "she" was actually a man disguised as a woman. Who then wore male clothes and armor on the battlefield.
The mid-Twentieth Century aerialist Barbette dressed as a woman while performing his act and no less than Jean Cocteau believed him to be the pinnacle of artistic artifice, indistinguishable from a woman until the end of his act when he took off his wig and made exaggeratedly masculine gestures. Thought to be the inspiration for Viktor und Viktoria (and later Victor Victoria).
One famous literary hoax was that of JT Leroy, a young gender-dysphoric gay man who wrote semi-autobiographical novels and short stories based on his abusive childhood and his life as a sex worker. The hoax was that he didn't exist; the books were written by a woman, Laura Albert, and Leroy's public face was played by her sister-in-law, Savannah Knoop. This trope came into play in how Knoop got away with it unchallenged for so long; they disguised themself in drag as an effeminate man, but when pressed would explain that "he" was undergoing a gender transition to female and dressed as a man in public for privacy reasons. Even without this explanation (which is already complex enough), many of the photoshoots Knoop took part in as Leroy involved wearing dresses and make-up. The title of Knoop's autobiography regarding this period of their life is called, appropriately enough, "Girl Boy Girl".

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

Recursive Crossdressing

Examples:

Previous

Index

Next