10 Cross-Dressing Characters on Film

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The Sherlock Holmes sequel is headed to theaters tomorrow, giving the great detective and his sidekick Dr. Watson another opportunity to outsmart their nefarious adversary, Professor Moriarty. One scene finds the titular character disguised as a woman — a look that RDJ describes as a cross between “Arnold Schwarzenegger’s dwarf brother” and “Robert Smith from The Cure.” Hot? Hollywood’s been dressing in drag since the dawn of cinema. Although movies like Adam Sandler’s latest disaster Jack and Jill try to use cross-dressing for comedic effect, they often fail miserably. The top five grossing films that explore gender bending (superficially anyway) are all comedies, but some films take cross-dressing more seriously and use it as a dramatic way to examine fluidity in gender and identity. We’ve spotlighted 10 films that find characters cross-dressing for their parts. There are plenty to mention, so leave us your picks below after you check out our list past the break.

Some Like it Hot

One of the earliest cross-dressing comedy capers, screwball classic Some Like it Hot finds Tony Curtis and Jack Lemmon in heels and skirts when they join an all-girl orchestra and hit the road on the lam from the mob. Once they meet the sultry Sugar Kane (Marilyn Monroe) — and become seduced by the possibility of extra female attention — they decide to stick with the mascara. Of course, things get complicated when Curtis’ Josephine falls in love with Sugar. What follows is a charming, burlesque-worthy farce of the campiest order that simmers with clever innuendo. The movie was one of several that helped rid Hollywood of the old Production Code — a moral censorship group that left directors hamstrung and unable to explore edgier themes in their works.

The Tyler Perry/Big Momma/Madea movies of the world

Perhaps the crudest and most grotesque of cross-dressing caricatures and stereotypes, one Tyler Perry/Big Momma movie in the world is too many. Actors like Idris Elba have been a voice against the buffoonish films for a while now, aiming to bring more positive African American roles to the big screen. Contrary to what Hollywood studios seem to think, most African Americans are watching the same films as other audiences and, gee, might not appreciate the strange and often degrading characters that Tyler Perry’s Madea or Martin Lawrence’s Big Momma bring to the comedy table. Building your entire movie around the equivalent of a fart joke is never a good idea. What could have been a mildly funny sight gag becomes an obvious concept that aims for the low hanging fruit. Cut it out, Hollywood.

Psycho

A psychoanalytic nightmare if there ever was one, Hitchcock’s Psycho is one of several movies where the auteur displayed fascinating sex and gender themes. During Hitchcock’s time, cross-dressing and homosexuality were usually thought to be one and the same, creating an air of ambiguity around several of the filmmaker’s characters. The director did emphatically demonstrate that Psycho‘s Norman Bates was attracted to women in several scenes. Some critics, however, see Perkins’ cross-dressing performance as more than just an Oedipal delusion and closer to a kind of homosexual code.

Female Trouble

Cult cross-dressing icon Divine (Harris Glenn Milstead) played her first male role in a movie for John Waters’ 1974 Female Trouble. The star took on double duty, though, playing both a man and a woman — and both at the same time for one scene where the B-movie thespian actually has sex with himself/herself. Divine’s glamorous crime spree comes with all the usual Waters moments. More importantly, it’s proof that the larger than life star was one of the first to transcend all preconceived notions of beauty, gender, sexuality — leaving many to squirm against its blurry lines, forced to reconsider everything they thought they knew.

Just One of the Guys

Most teen sex comedies of the 1980s centered around the nerd’s never-ending quest to lose “it,” which is why Lisa Gottlieb’s Just One of the Guys was like a breath of fresh air — and funny as hell to boot. Joyce Hyser’s Terri Griffith is the hot high school chick who wants to be taken seriously as a journalist. Natch, she goes undercover at a rival school dressed as a boy (and totally looking like Ralph Macchio). There she tries to prove her worth and ends up falling in love. It’s a journey of self-discovery with a few serious twinges about gender identity that offers more than just boobs. While there is lots of that too, the sexy stuff is bookended by a sharper narrative usually missing from most teen pics.

The Birdcage

We could have easily listed Priscilla, Queen of the Desert, To Wong Foo, or another fun-loving drag comedy instead of The Birdcage here, because generally they all aim for the same themes about liberation and acceptance. The Mike Nichols’ directed film — La cage aux folles for Middle America — isn’t aiming to break any cross-dressing cliches, but it does embrace them and sashay like crazy. The film was GLAAD approved for ” … going beyond the stereotypes to see the character’s depth and humanity. The film celebrates differences and points out the outrageousness of hiding those differences.”

Party Monster

Party Monster brought 1980’s New York City club kids to the mainstream, telling the sad story of real-life party promoter Michael Alig (Macaulay Culkin). It’s kind of a glittery mess that is as much of a cipher as the Ketamine kids at the center of its story, but tries to posit that the fantasy is an illusion to conceal an inner void. Seth Green’s trust fund queen James St. James — who actually wrote the book the film is based on, Disco Bloodbath — humanizes the monsters that the daytime talk show circuit loved to demonize.

Ma vie en rose

Seven-year-old Ludovic is convinced that he’s really a girl in Alain Berliner’s Ma vie en rose (My Life in Pink). He wears dresses, idolizes a TV princess named Pam, and struggles to convince his family that he was born in the wrong body while they alternate between humoring him and panicking about their own reputation. Neighborhood hysteria ensues when Ludovic draws a friend into his fantasy world — gently prodding us to consider our own tolerance for such differences.

Shakespeare in Love

Directly referencing the prolific works of the famous Elizabethan bard, 1998’s romantic-comedy Shakespeare in Love toys with the playwright’s historical use of disguise and mistaken identity. A young girl wants to be center stage, but women were banned from performing alongside men, which forces her to adopt a male persona. While the fake mustache made Gwyneth Paltrow twitch her itchy nose adorably Bewitched-style, cross-dressing in the movie also brings up compelling real-life political/dramatic connections that influenced the scribe’s work.

White Chicks

Sorry, but dressing like skinny white girls instead of obese black women isn’t any less idiotic. White Girls doesn’t try to stereotype white culture as much as it takes aim at the celebutantes of the universe. It could have been a cleverly subversive way to make a grander statement about gender, race, and culture (these guys did make In Living Color, after all), but it’s just another boring fart joke.