Men in Dresses: Thoughts on Crossdressing Comedies

People wearing clothes that aren’t their normal clothes! Hilarious!

For as long as we’ve had visual storytelling, we’ve had crossdressing narratives. Among them, probably the most famous in the English speaking world is Shakespeare’s Twelfth Night, which has been adapted into film and done on stage dozens of times in dozens of ways. In the world of film, some of the most highly thought of comedies of our time, Some Like it Hot, Tootsie, and Victor/Victoria all take on this story to hilarious ends. More recently, comedies like White Chicks and She’s the Man (an adaptation of Twelfth Night) update the story for a modern audience. Even media from other countries, like Coffee Prince from Korea and Ouran High School Host Club from Japan, get in on the crossdressing game.

So, why is it that the crossdressing comedy is such a widespread, and often beloved, trope?

First of all, the crossdressing comedy inherently offers up a few classic hallmarks of good comedy. Normally, these films involve one person pretending to be another, which leads to a lot of potential for mistaken identity and wacky hijinks. It also puts our comedy protagonist out of their element, letting them run into a lot of blunders and slip ups that they have the rectify to hilarious consequences. Simply put, comedy needs conflict, and a lot of comedy is possible when a person is taken far outside of their comfort zone.

In somewhat more offensive versions of the crossdressing comedy, the humor comes from gay panic humor. If you’re having a character pretend to be a different gender, it’s almost required that you have someone of their own gender attracted to their alter ego. If a man being attracted to another man is inherently funny to you, then this is a guaranteed laugh riot. Luckily, most versions of this story avoid this route, and let the character’s relationships be more complicated, and therefore funnier, than simple gay panic humor.

The biggest source of comedy that the crossdressing narrative offers is in its unique ability to parody gender roles, which can be played for simultaneous comedy and drama. In Tootsie, the audience laughs at Dustin Hoffman’s initial insane scheme to dress as a woman, but the plot quickly shifts its focus to the sexism and discrimination he faces as Tootsie. In Victor/Victoria, Victoria’s mobster love interest is terrified of his attraction to the presumed male Victor, but also struggles with what his relationship with the sensitive, emotional man means for his masculinity.

Men and women aren’t necessarily from Mars and Venus, but they do experience society differently, and the crossdressing film allows one character to be put into another gender’s experience of the world. Even at its wackiest, it can challenge our notions of what the natures of men and women are, and of how gender roles in society affect each of us. Unlike some movies that attempt to pull off the “Man vs. Woman” storyline, like What Women Want, the humor of a crossdressing comedy is usually derived from the artifice of genders, rather than the differences between them. It’s not that a man is different once he puts on heels, it’s that society sees him differently right away, and the difference is ripe for humor.

Of course, one complication in the future of this genre is the continued efforts to break down the gender binary, and the existence of real gender non-conforming persons in the world. If it’s okay to laugh at a man in a dress, then is it equally acceptable to laugh at a person assigned male at birth who now dresses as a woman, even if they identify as a woman? It definitely is not, which makes the question of whether or not crossdressing comedies can still be deemed acceptable a real one to consider.

Luckily, though they are still rare, this issue can be someone rectified with more comedies, outside the crossdressing genre, that feature real transgender and gender nonconforming characters in lead roles. A comedy like Some Like It Hot, about two men who identify as men who are forced to pretend to be women to run away from the mob, is clearly a separate genre from something like Kinky Boots, a comedy where the humor derives not from the fact that one of the main characters is in a dress, but from that character’s relationship with those around her.

As we continue to complicate gender, there’s always the chance the classic crossdressing comedy might go out of style, but I highly doubt it’ll ever go away completely. Mistaken identities and taking people out of their comfort zones are two fundamental elements of the classic farce, and the crossdressing comedy pairs those situations with the potential for some satirical humor about gender as well. As the mainstream audience’s understanding of gender evolves, so too can the crossdressing comedy, and hopefully future gender satires can address the broad range of gender experiences in the world.

It might take us some time to get there, but hey, nobody’s perfect.