A Short History of Cross-Dressing in Media


All the hubbub about Brian Bedford’s spectacular performance as Lady Bracknell in the recent Broadway revival of The Importance of Being Earnest has gotten us thinking. So much media in our culture revolves around, or at least includes, elements of cross-dressing or gender confusion, whether to comic or dramatic effect. Is this an evolution towards greater acceptance and understanding of all, or just, in some way, a deeply ingrained human impulse? Of course, cross-dressing is no new trend. The phenomenon is evident in everything from Norse and Hindu mythology to figures that shaped actual historical events (usually in the form of women dressing up as men to fight wars or be pirates, for some reason) to literature, theater, film and every kind of media in between. There are hundreds of examples, so there’s no way to document them all here, but the trajectory of our favorites still has some bearing on the largeness of the phenomenon. Click through for out brief history of cross-dressing in media.

1592 – First performance of Henry VI, Part 1, Shakespeare’s first play

Shakespeare did not invent the custom of cross-dressing in theater. After all, everyone learned in their 9th grade English classes that it was illegal for women to perform in Renaissance theaters, and so all of Shakespeare’s plays were performed by men in ever role. Since a good story always involves a lady in one way or another, every play in the period would have been an instance of theatrical cross-dressing. However, Shakespeare was perhaps more interested in or more clever with this tradition than most, working cross-dressing into many of his plays to achieve a meta comedy: a man dressing up as a woman dressing up as a man, sometimes again dressing up as a woman. Even in Henry VI, his first produced play, he depicts Joan of Arc, an important historical cross-dresser, and he went on to chase the trope in plays like Twelfth Night or What You Will, As You Like It, and The Merchant of Venice.

1915 – Charlie Chaplin takes off his moustache in The Masquerader

Chaplin was the ultimate physical comedian, so it makes sense that he would extend the comedy inherent in his body in every way imaginable. This was Chaplin’s 24th film — the first, though not the last, where he dresses up as a female to trick a man. He plays a woman in another 1914 film, A Busy Day, though that film lacks the element of the reveal.

1950 – Bugs Bunny dresses up as a girl bunny to fool Elmer Fudd

The Rabbit of Seville was one of many instances where Bugs dressed up as a girl in order to confound, harass and brutalize Elmer Fudd and the other semi-villains in his universe. Though we’re not sure what this says about women (probably nothing, Bugs attacked in every costume imaginable), we like to think Bugs has a healthy appreciation for ironic mischief and a secret ability to confuse/inspire the children. Or maybe just Garth.

Garth: Did you ever find Bugs Bunny attractive when he put on a dress and played girl bunny? Wayne: No! [laughing] No. Garth: Neither did I. I was just asking.

1959 – “Well, nobody’s perfect,” in Some Like It Hot

This film is a little Shakespearian itself in its layers of costume and mistaken identity. Two male musicians, Joe and Jerry, witness a mob massacre, and go into hiding as members of an all-girl band on tour. Unfortunately, they both fall in love with Marilyn Monroe, and Osgood, a male millionaire falls in love with Jerry in his feminine disguise. At the end, in a desperate attempt to call off the wedding, Jerry flings off his disguise and shouts, “I’m a man!” Osgood contemplates this development and shrugs, “Well, nobody’s perfect.” In 2000, Some Like It Hot was declared by the American Film Institute to be the best American comedic film of all time.

1975 – The Rocky Horror Picture Show

There may not be a more iconic cult cross-dresser than Tim Curry’s “sweet transvestite” Dr. Frank-N-Furter in his ever-present, enormous fake pearls. We weren’t allowed to see this movie until we were 18, but not because it was scandalous — our dad just didn’t want us to miss the impact of the opening lips on the big screen.

1982 – Dustin Hoffman is a better man as Tootsie

Tootsie stars Dustin Hoffman as Michael, a perfectionist actor who can’t get a job until he dresses up like a lady. Of course, the usual inappropriate falling in love hijinks ensue, until at the end of the film, Michael tells his love interest, “I was a better man with you as a woman than I ever was with a woman as a man.” Read that again, it takes a second. In 1988, Tootsie was deemed “culturally significant” and a copy has accordingly been preserved in the National Film Registry.

1988 – In John Waters’ film Hairspray, Divine plays the protagonist’s mother, Edna Turnblad

Though a man (even when that man is Divine) playing an overweight, gravel-voiced woman is small potatoes considering what Waters is capable of, it’s notable that the role has been reprised by a man in every subsequent staging of the story. Most significantly, after a 2002 run on Broadway with Edna played by Harvey Fierstein, a 2007 film remake of the Broadway version starred everyone’s second favorite Scientologist John Travolta in the role. Honestly, we kind of hated everything that happened after Waters’ original film, but maybe that’s just the hipster in us. Still, can’t beat Travolta as a fat lady. Or anything with Allison Janney.

1994 – Rent makes every teenage girl everywhere cool with cross-dressing

Because no one could ever be bigoted about Angel.

1998 – Hua Mulan becomes Fa Mulan

Cross-dressing for kids! The Disney movie Mulan is based on the Chinese folk hero Hua Mulan, who joined the army instead of her ailing father. According to the original legend, she fought for twelve years and eared twelve ranks, but refused them all and retired. In the Disney version, she also gets to marry her foxy commanding officer. And also she has a pet dragon that sounds suspiciously like Eddie Murphy.

2010 – Prospero becomes Prospera in Julie Taymor’s The Tempest

Further conflating all the Shakespeare cross-dressing meta commentary, Julie Taymor cast Helen Mirren for the part of the sorcerer Prospero – ahem, Prospera – in her 2010 film adaptation of The Tempest. Though the film was widely panned, the gender change opens up a range of new interpretations in the relationship between Miranda and Prospero/a, and doubles the wrongdoing in Prospera’s original forced exile from the throne.

2011 – Brian Bedford plays Lady Bracknell in The Importance of Being Earnest

In the Broadway revival of Oscar Wilde’s classic play, Brian Bedford plays the gloriously uptight paragon of social correctness, Lady Bracknell. He originated in the role in 2009 at the Stratford Shakespeare Festival in Ontario, but the play’s new run on Broadway has the New York critics all a-titter. According to the New York Times , it is not entirely new for the role to be played by a man, but it is relatively unusual for it to be played completely straight, as Bedford does. He has no need for any winking gender-role jokes, preferring to milk the role for its inherent humour — of which there is plenty. Perhaps this is a signal that our culture is moving even further into gender-neutral territory with acting — that is, if you’re good enough.

Obviously we left a million things out — let us know your favorites in the comments!