Summary
- Cross-dressing has a complicated history within mainstream society, neither fully embraced nor rejected, often feared and enshrined in pop culture.
- Men wearing women's clothes has been a long-standing comedy staple, from Shakespeare to Milton Berle, but the trend has faced backlash for potentially weaponizing gender-bending.
- The current cultural climate surrounding transgender politics has made cross-dressing a sensitive issue, potentially seen as a slight or cultural appropriation, risking the end of mainstream acceptance.
No fashion concept has undergone as much of a reevaluation in recent memory as that of cross-dressing. Films once deemed risqué or daring are now mundane or hard to relate to. The Adventures of Priscilla, Queen of the Desert is so time-specific it only makes sense in the narrow gap pre-millenium before the acceptance of gay and lesbian rights.
Despite associations with queer culture and the larger Pride movement, cross-dressing has a somewhat baffling history within mainstream straight society, always lingering on the peripheral, neither embraced nor wholly rejected. It has been feared as much as it has been enshrined in pop culture history. For every "empowering" moment like RuPaul's Drag Race, we have a litany of Bosom Buddies. For anyone terrified about normalizing drag culture, consult with your great-grandparents who watched Milton Berle wear a wedding dress on national primetime TV in 1951, cracking jokes about his sponsor. Cross-dressing didn’t change — we did.
Men wearing women’s clothes has always been one of the quickest and easiest ways to get a chuckle from an audience. Perhaps that’s a problem. No one really has ever known whether to take it seriously or not, whether it's a means to an end or an identity. Confused? So are some cross-dressers themselves, as we will soon see.
Cinch your garter-belt tight and make sure you are wearing some comfy pumps, the rabbit hole goes deep.
The Oldest Comedy Staple
Since the time of Shakespeare, men have been slipping into ladies’ attire. Actresses were barred from the stage in the 16th Century, forcing men to perform in every role, often to (intentionally) comical effect. Although cross-dressing has a long track record, it wasn’t until the 50s where Milton Berle made it mainstream to the masses, donning women’s clothes on his TV show. On film, new ground was broken with the film Some Like it Hot, which hid queer undertones in plain sight. Women partook in breaking the rules, too, but never to the same level of shock, Marlene Dietrich's smooch with a woman while in a tuxedo ignored by pearl-clutchers and censors.
In the decades following “Uncle Miltie,” audiences would be bombarded by improv troupes such as Monty Python, Saturday Night Live, Kids in the Hall, and The Whitest Kids You Know running with the gag. The act of dressing in the clothes of the opposite gender usually half (if not the entirety) of the joke, Terry Sweeney relegated to playing Nancy Reagan and Joan Rivers out of SNL writers’ apathy and bewilderment toward an openly-gay cast member. While straight men were attempting to break into gender-bender to get famous, many gays were ironically trying to escape the cliché before it type-cast them into oblivion.
The Backlash
The trend might never have gone questioned if not for Dave Chappelle, who voiced outrage at the way it is used. For many people, gender-bending is wielded as a weapon, or so he claimed in a 2006 interview with Oprah Winfrey. Hedging his statement, he told her that his distrust with the entertainment industry began when he noticed that “they put every Black man in the movies in a dress,” insinuating that their careers would be sabotaged if they refused to submit.
In the interview, Chappelle only singled out Martin Lawrence, but his accusations speak to a broader comedy trope that encompasses Flip Wilson in the 70s, Jamie Foxx’s turn as Wanda in In Living Color, and Eddie Murphy’s female bodysuit in Norbit.
Chappelle’s take doesn’t really square with the long-storied history of men wearing women’s clothes for laughs — it was standard by the eighties — but he’s not alone in his philosophy. Chappelle was vague who “they” were, but comedian Katt Williams left no doubt. It has only spread on the internet underground, where the notion that Black men in particular are forced to put on a dress is part of an Illuminati conspiracy. We can’t make this up. Williams has gone on the record repeatedly claiming that all Black male performers will inevitably have to humiliate themselves when their “turn” comes up.
An Endangered Species?
Were Williams and Chappelle right? That’s a matter for you to untangle. It might not matter in the long run. Transgender politics is so radioactive at the moment that the likelihood of a film like Mrs. Doubtfire or The Birdcage ever becoming a mainstream hit again is impossible by mere fact of political baggage that comes with the issue. Any act of cross-dressing could be seen a potential slight to either side eager to sniff out any insult or hidden message. Those that are transgender could perceive it as an insult, and those opposed could see it as indoctrination. It’s been ruined for everyone.
If the fractures in the current culture wars escalate, it isn’t impossible that straight men in drag might someday be seen the same as Awkwafina's Compton-inspired accent. It’s been 30 years since the great RuPaul-Milton Berle incident at the MTV Awards, proving that not even the drag community is without its own internal divisions. Berle and the famous (or infamous) Dame Edna represent an older, straight branch of the cross-dressing contingent, one who don’t view it as a political statement, going so far as criticizing the transgender movement as dangerous. More contemporary cross-dressers, who usually identify as LGBTQ+, stand diametrically opposed to those who used it as a sight-gag.
The specter of blackface comparisons are not too far behind when it comes to representation and identity. It could be only matter of time before cross-dressing is designated a kind of cultural appropriation as part of a possible schism.