Cross-Dressing at the Crossroads: A Brief History of Drag in Comedy

Comedy Features Drag
Cross-Dressing at the Crossroads: A Brief History of Drag in Comedy

In 1993, worlds collided when Milton “Mr. Television” Berle and RuPaul were paired up to present at the MTV VMAs together. At the time, the awkward coupling seemed like nothing more than another bizarre feat of award show booking. But in hindsight, it was a moment that signaled a significant turning point—a prescient preview of things to come.

In 1948, Berle was television’s first superstar, often utilizing the reliable burlesque trope of putting a man in a woman’s dress on his weekly series, The Texaco Star Theater. Back then, adopting the implied but never explicit characteristics of gay or trans people was reflective of an aggressively hetero-dominant culture. But 45 years later, what was so startling in the televised exchange between the octogenarian and the towering host of Drag Race was the palpable tension. After “Uncle Miltie” received an appreciative laugh from the audience on his joke about being a “straight man,” he went on to follow their scripted patter about how he also used to wear gowns on TV. RuPaul then ad-libbed “And now you wear diapers.” Berle was furious, later grousing how he was blindsided by the cheap shot from “Rude Paul.” But that one line seemed to come from a voice of a long-oppressed subculture fighting out of a corner. No longer willing to be reduced to a caricature or a sight gag, drag was now something else: an identity to be embraced.

After long-standing traditions of men dressed as women in Greek and Shakespearean theater, one of the first and most celebrated contemporary cross-dressing comedies was the 1892 play Charley’s Aunt. Originally written for the English stage, it was translated into over 80 languages, spawning multiple film adaptations and the hit Broadway musical Where’s Charley? Its basic premise relied on a heterosexual man needing to assume the guise of a woman, with the comedy ensuing from the juxtaposition of the challenges to his masculinity. Cross-dressing out of necessity creating laughs rooted in traditional gender identity continued as a reliable comic premise for the next century, from Billy Wilder’s 1959 classic Some Like It Hot, to Tom Hanks’s breakout 1980s sitcom Bosom Buddies. Even in these memorable projects, the formula remained the same: straight men in women’s clothes speaking in high-pitched voices equals laughs. Mainstream society accepted that there were hard borders on masculine and feminine identity. To cross them and then bear the consequences of doing so always resulted in high concept hijinks and hilarity.

In the sketch comedy/variety world, the conventions of cross-dressing men were similarly consistent, although slightly different. The comedy came from the accepted ridiculousness of guys in drag, but the men generally played female characters. From Monty Python to The Kids in the Hall to multiple generations of guys on Saturday Night Live, all of these (mostly) straight men made gender-bending funny without ever making the fact that they were doing it the textual premise. It was just understood that the very act of men in skirts and heels was funny. With race added into the mix ideas of traditional African-American masculinity could be inverted, and Flip Wilson as Geraldine, Martin Lawrence as Sheneneh and Jamie Foxx as Wanda elicited howls of laughter for many years.

The shift in the public’s attitude started in the 1970s, when androgyny found early acceptance in the rock music scene with the New York Dolls, Iggy Pop, Lou Reed and David Bowie. CBGB regular Jayne County became one of the first openly transgender performers. Around this same time, John Waters’s 1972 underground film Pink Flamingos cracked a counterculture closet door for the cross-dressing Divine, later moving him more into the mainstream with Waters’s 1988 classic Hairspray, which spawned a hit musical and a film version of the musical. And then there was Rocky Horror. First produced as a stage musical in 1973 in London, Richard O’Brien’s intersection of ‘70s glam rock and comedy became a 1975 cult classic midnight movie that grew into a mini-movement for generations of devotees who identified with, rather than laughed at, the characters and their explorations of fluid sexuality. Even the brilliant and progressive film and TV writer Larry Gelbart evolved from the sight gag of Jamie Farr’s cross-dressing Klinger on the series M*A*S*H in the ‘70s to the layered exploration of male femininity and feminism in his 1982 film Tootsie. So by the late 1980s and early 1990s, when British comedian Eddie Izzard burst onto the scene as a heterosexual “executive transvestite,” prevailing cultural attitudes were ready to embrace less rigid constructs of gender.

Change is always gradual. Especially in comedy, which both reflects and drives perceptions. Everything on this journey must be seen in the context of its time. But in tracing our growth, it’s heartening to see where we’re headed. This past season of SNL upended the formula by casting Melissa McCarthy as Sean Spicer and Kate McKinnon as Jeff Sessions, and they enjoyed their biggest ratings in years. Even Tyler Perry’s Madea and Louie Anderson as Zach Galifianakis’s mom on the FX series Baskets are more nuanced than the old drag caricatures. Gay, straight, trans or cisgender, our ability to find a common humanity in all means our cross-dressing comedy can and will go deeper than the dress.

Dan Pasternack is a writer and a producer. Follow him on Twitter.

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