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=On the Stage= A convention that has been in place throughout entertainment since the age of Grecian theatre, cross-dressing has undergone vast changes as society’s view of men and women’s roles in the world continues to shift. What began as a needs-based response to the fact that women weren’t allowed on stage transformed into a comedic tool in order to “neutralize” the sexuality of a woman (Gewertz citation added here). From Greece to England to Japan to America, this practice can be found in action.

Cross Dressing as Custom in Performance
Elizabethan England

In Renaissance England it was illegal for women to perform in theatres,[4] so female roles in the plays of Shakespeare and his contemporary playwrights were originally played by cross-dressing men or boys. Therefore the original productions of the above-mentioned Shakespeare plays actually involved double-cross-dressing: male actors playing female characters disguising themselves as males. Academic research into the contemporary attitudes towards the practise have yielded a variety of interpretations. Laura Levine argues that "an all-male acting troupe was the natural and unremarkable product of a culture whose conception of gender was "teleologically male""; she also suggests that contemporary protests against the practise (believing it made young actors "effeminate") reflected "deep-seated fears that the self was not stable and fixed but unstable and monstrous and infinitely malleable unless strictly controlled.

Japan

All roles in Japanese Noh dramas are traditionally played by male actors. Actors playing female roles wear feminine costumes and female-featured masks. Japanese Kabuki theatre began in the 17th century with all-female troupes performing both male and female roles. In 1629 the disrepute of kabuki performances (or of their audiences) led to the banning of women from the stage, but kabuki's great popularity inspired the formation of all-male troupes to carry on the theatrical form. In Kabuki, the portrayal of female characters by men is known as onnagata. The practice is detailed in a story of the same name by the Japanese writer, Yukio Mishima. The Takarazuka Revue is a contemporary all-female Japanese acting company, known for their elaborate productions of stage musicals. Takarazuka actresses specialize in either male or female roles, with male role actresses receiving top billing.

China

In ancient China, nearly all the characters in Chinese Opera were performed by men, so that all the male actors who played the role of a female were cross-dressing. A famous cross-dressing opera singer is Mei Lanfang. From early 20th century, Shanghai yue opera (or Shaoxin opera) is developed from all male to all female genre. Although male performers were introduced into this opera in 1950s and 1960s, today, Shanghai yueju (yue opera) is still associated as the only all female opera and the second most popular opera in China.

Italy

Cherubino of The Marriage of Figaro (Beaumarchais): This opera buffa by Mozart has historically cast the Count’s page as a mezzo-soprano in order to highlight the youth of the character. Even Commedia dell'arte, deals with shared space between men and women. What was more telling of the time than crossing-gender, was women crossing-class as one academic, Christine Varholy, claims that it was a "tell-tale sign of whoredom."

USA

In pantomime plays that are traditionally adaptations of fairy tales and performed around Christmastide, the role of lead male was once commonly played by a principal boy—a young, attractive, female. The role of a pantomime dame, a middle aged woman played by a man for comic relief, is still one of the mainstays of the Pantomime.

Cross-Dressing Stage Performers
While some performers cross-dressed only for certain roles, others achieved great success and became best known for their cross-dressing abilities and continued performances.

1600s

A historical example of an actress famous for trouser roles is Julie d'Aubigny, aka "La Maupin" (1670–1707), who dressed in male clothing both on and off stage.

1800s

One of the most famous cross-dressing actresses was Vesta Tilley, who grew up working in a music hall from five years old well into her fifties. Her famous tendency to dress as a man and act out "masculine" scenes and roles made her the highest paid woman in Britain by the late 1890’s.[6]

Fred Foster and Sarah Lane were two English stage actors of the late 19th century who cross-dressed as the opposite sex, Fred as the Queen and Sarah as a French Gentleman. In true Vaudevillian form, they performed small plays in which Fred, as the queen, would have to fend off the advances of the Gentleman played by Sarah. This was a large satirical social commentary at the time of the gendered roles in society, these two actors were able to perform opposing gender roles for laughs. In 1844, Sarah Louisa Fairbrother played Abdullah, a male character, in the pantomime of Open Sesame.

Julian Eltinge was a particularly popular actor during this time specifically for his ability to portray a woman’s character. As Mark Fearnow mentions in the Oxford Encyclopedia for Theatre and Performance, women audience members accepted his femininity so readily that they were able to simply “admire his elaborate costumes.” He was the first female impersonator to star in a Broadway show.

Neil Burgess was one of the most celebrated female impersonators of the late 19th century. He often portrayed older, ailing women such as Widow Bedott in 1879 or Auntie Abigail in the play The County Fair in 1889. He was remembered by George Odell as “not the least bit effeminate… and yet he was Widow Bedott to the life.”

1913- Present

Peter Pan the musical, based off the book by J.M. Barrie tells a classic tale of the little boy who never grows up is nearly always cast as a woman within the theatre. Peter has been played by Mary Martin, Sandy Duncan, Cathy Rigby, and Allison Williams. The first and most popular Peter Pan for nearly fifty years was the one and only Maude Adams. Beloved by fans and even J.M. Barrie himself, Adams set the tone for both fashion and heart of the young boy.

The Kids in the Hall comedy troupe often dress up as female characters. In contrast to Monty Python who dressed as women in an exaggerated fashion for comedic purposes, The Kids in the Hall usually played women straight, their reasoning for cross-dressing being that there are few if any women involved in their projects. This has gone on to be one of the groups defining characteristics.

Eddie Izzard, a British stand-up comedian and actor, states that he has cross-dressed his entire life. He often performs his act in feminine clothing, and has discussed his cross dressing as part of his act. He calls himself an 'executive transvestite'.

The British writer, presenter and actor Richard O'Brien sometimes cross-dresses and ran a "Transfandango" ball aimed at transgendered people of all kinds in aid of charity for several years.

Cross-Dressing Characters
Several plays and musicals include characters whose impetus to cross-dress was source of drama or comedy. This theatrical convention was crucial to the story that was being told.

Shakespeare

William Shakespeare’s plays are well known for their complex interpretations of cross-dressing.

Portia and her maid in The Merchant of Venice dress as men to plead in court on the merchant's behalf; in the same play, Shylock's daughter Jessica dresses as a man to elope with her Christian lover.

Viola, the protagonist of Twelfth Night deals extensively with cross-dressing. She disguises herself as a man, herself falls in love with a man, and is then wooed by a woman the man loves.

Rosalind and Celia flee court in As You Like It, Rosalind dresses, for their protection, as a man. However, as a way to further complicate the situation for comedic effect, Shakespeare has Rosalind's male character Ganymede dress as a woman to help a male friend, Orlando de Boys, practice wooing Rosalind, with whom he is smitten, while at the same time fending off the affections Phoebe has for "Ganymede". In other words, it is a man, (the actor), dressing as a woman, dressing as a man, dressing as a woman.

19th Century

In Noah Mordecai’s 1819 play She Would Be a Soldier, the character Christine cross dresses as an American soldier to follow the man she loves to an army camp and passes as male. Such a character in the early 19th century was bold and defied many tropes of performed femininity.

The 1892 English comedy Charley's Aunt features a male character, Lord Fancourt Babberly, who is persuaded by his friends to impersonate his friend Charley’s aunt. While acting as the old aunt Donna Lucia, Babberly complicates romantic relationships and cheeky confusion abounds.

20th Century

David Henry Hwang's 1988 play M. Butterfly focuses on a love affair between a French diplomat and a male Beijing opera singer who plays dan (旦), or female, roles.

In the 1996 musical Rent, Angel is an example of a modern cross-dresser.

Although there is some dispute as to whether the character is transgendered or simply a cross-dresser, the character of Hedwig from the musical Hedwig and the Angry Inch is another modern drag queen. The musical also features a male character played traditionally by a female actress, although the character's true gender is deliberately left with slight ambiguity.

In Clue: The Musical, Mrs. White is usually played by a man. The character description reads: "MRS. WHITE - fun-loving cockney maid, portrayed by a man; plays 40s-50s; wide vocal range"

In all versions of Hairspray, Edna Turnblad has been played by Harvey Fierstein, Michael Ball, Trevor Ashley, Mark Benton, and John Travolta to name a few.

=On the Screen=

The same convention readily translated into the world of film and television as technology advanced.

Cross-Dressing Screen Performers
Certain film performers became well known for their iconic cross-dressing roles on the screen.

1970s-80s

The Monty Python troupe have been known to cross dress for comedic purposes in their TV series and films. The troupe usually dress up as older, more unarousing women referred to by the troupe as "pepperpots". Although member Terry Jones was most famous for his female characters, all the members have been seen in drag in one sketch or another; members Michael Palin and Eric Idle have been said to look the most feminine, Graham Chapman specialized in screeching, annoying housewives and John Cleese, whom the troupe has said is the most hilarious in drag, appears so extremely unfeminine, with his square chin and six-foot, five-inch frame that it is funny. Cleese also wore female clothes while appearing as himself in a magazine advertisement for American Express. For more information about cross-dressing in movies and television, see the article Cross-dressing in film and television.
 * Monty Python's Flying Circus also did a sketch called "The Lumberjack Song," about a lumberjack who likes to "put on women's clothing and hang around in bars."

In Star Wars Episode IV: A New Hope, the male alien bounty hunter Greedo was portrayed by both a male and a female, each acting in different shots.

2000s

In addition to her many roles in the 2003 TV Miniseries, Angels In America, Meryl Streep took on the historically male role of a Rabbi.

Matt Lucas and David Walliams regularly cross-dress in the Little Britain television comedy show, with Lucas in particular often somewhat more feminine and convincing in his appearance and performances than cross-dressing comedians of the past. The two also sometimes play a pair of unconvincing transvestites as a parody of some cross-dressers who try to act in a stereotypically feminine way while not succeeding in "passing" as women.

Tyler Perry cross dresses to play the female character Madea in several of his films.

Michelle Ehlen plays a butch lesbian actress who gets cast as a man in a film in the comedic feature Butch Jamie.

Cross-Dressing Film Characters
1900s

Joe and Jerry in Billy Wilder's 1959 Some Like It Hot, two struggling musicians, have to dress up as women to escape the ire of gangsters. The film is a remake by Wilder and I. A. L. Diamond a 1935 French movie, Fanfare d'Amour, from the story by Robert Thoeren and Michael Logan, which was itself remade in 1951 by German director Kurt Hoffmann as Fanfaren der Liebe. An NPR’s retrospective look on the effects of the Hays Code in Hollywood speaks to this dichotomy when author, Bob Mondello claims:

"With its cross-dressing and homosexual pairings, Some Like It Hot was released in 1959 without a certificate of approval from the Production Code Administration. The Tony Curtis-Jack Lemmon comedy was an overwhelming success, weakening the authority of the code."

In Blake Edwards' 1982 musical comedy film Victor Victoria, Victoria Grant, a struggling soprano, is unable to find work but she finds success when she becomes "Count Victor Grazinski", a female impersonator. The film is a remake of Viktor und Viktoria, a German film of 1933.

The 1949 film I Was a Male War Bride tells the story of a french soldier who falls in love with an American nurse. The soldier, played by Cary Grant, must impersonate a nurse and claim to be a ‘war bride’ to come back to the United States with the nurse he plans to marry.

Dr. Frank-N-Furter in the Rocky Horror Picture Show wore nothing but women's clothing the entire movie/play.

In The Drew Carey Show, Drew's brother, Steve Carey, is a cross-dresser.

Robin Williams played a father who dressed as a nanny to be with his children in the 1993 comedy Mrs. Doubtfire.

Dame Edna was an elderly drag queen with "wisteria-colored hair" who did international chat shows in the 1990s.