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 -- aren't I dear?

Ronnie Corbett: Oh, at least.

—The Two Ronnies, 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 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.

Examples of Recursive Crossdressing include:

Anime and Manga

Romeo X Juliet: Juliet gets to be a girl disguised as a boy disguised as a girl.
In the Manhwa 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.
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.
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.
Frequent in Ouran High School Host Club:
- Invoked when female fangirls giggle about how much they'd like to see Bifauxnen Fujioka Haruhi dressing in girls' clothing because "he" is so pretty.
- Haru is also dressed as a girl at one point for a Zuku production, and is really ridiculous-looking with strange ringlets and clown-like application of makeup that nearly descends into the Uncanny Valley. She's also 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.
- She also dresses in 17th century French "drag" for a host club event, as seen here.
- And 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.
- Haruhi has never tried to keep her gender a secret. The two reasons she doesn't tell anyone: 1. They didn't ask. 2. They enjoy their current preconceptions. The episode in which a secondary character discovers it is recommended.
In Ranma 1/2, 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.
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 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.
Played with in Family Compo: for Masahiko's entry ceremony, he asks his crossdressing aunt and uncle/adoptive parents to dress according to their biological sex. The result 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.
Minoru in AKB49: Ren'ai 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".

Film

Shakespeare in Love features Lady Viola dressing as a boy to get a part in a play; she ends up playing Juliet after having rehearsed as Romeo. Will Shakespeare knows she's really a woman, but the other actors either really don't or are hiding their knowledge even from her for most of the film. Which leads to Dame Judi Dench as Queen Elizabeth delivering a Crowning Moment of Awesome: After Viola has been accused of being a woman, Elizabeth observes her closely from all angles, then says "the illusion is remarkable." Of course, no one will contradict the Queen, so they have to let the illusion stand.
A minor example comes at the end of Miss Congeniality 2: 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 Life of Brian, many of the actors are men, who are playing women, who are disguising themselves as men so they can participate in stonings.
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 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 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.
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 Shan Yu and save China.
Transamerica, like many works where a non-TG actress plays a TG character, provides an example from the perspective of Real Life. Actress Felicity Huffman plays Bree, who is male-to-female transgender. Thus, in scenes where the preoperative Bree is cross-dressing, a woman is playing a character who is taking on the typical appearance of a woman.

Literature

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.
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 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 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 washerwomen. 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 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."
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 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.)
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.
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."

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 Star Trek: The Next Generation episode "The Outcast: an actress plays an androgynous alien who finds itself becoming female due to its attraction for Commander Riker, and has to cover this up because of societal taboo.
In Blackadder Goes Forth the character Bob, a Sweet Polly Oliver, steps in to replace a drag performer. The General 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.
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.
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.
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 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.
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.

Theatre

Practically every 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.

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—particularly when a female singer plays a guy who dresses as a woman at some point.
- The most famous example is probably The Marriage of Figaro, which was written just late enough that this sort of role would go to a woman rather than a castrato.
- 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 Der Rosenkavalier, where Octavian disguises himself as the maid Mariandel and fools the Baron completely.
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.
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.
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.

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 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.
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.

Web Comics

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.

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 recently-opened cafe in Tokyo features female staff dressed as young men in maid costumes. It caters to the fujoshi crowd.
If the Shakespeare example above wasn't 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 faux queens, women who purposefully adopt the mannerisms of drag queens - in music, Ana Matronic presents herself this way, as did Lady Gaga in her first few months in the spotlight.
Chevalier d'Eon was a French spy who lived as a man but frequently posed as a woman in the line of duty, and claimed to have been born a woman; eventually, it was demanded that d'Eon wear proper women's clothing, which d'Eon did until death, where the physicians examining him (or her) discovered he (or she) was anatomically male... making him/her a man claiming to be a woman but living as a man until ordered to live as a woman.