The History of Drag Representation in Television & Film Over the Decades
Long before RuPaul and his series RuPaul’s Drag Race put the art of drag at the forefront of pop culture when contestants began sashaying the runway in drag, cross-dressing, as it was once referred to, was popular in many movies and TV shows dating all the way back to the early 20th century, at least! Let’s recall some of those moments through the decades.
Charlie Chaplin was known to dress as a female counterpart in a couple of his silent films, such as The Masquerader (1914) and A Woman (1915) where he dresses as a lady so he can spend more time with his newly found sweetheart.
Fast forward to 1935 when Katharine Hepburn, in her first movie with another screen legend, Cary Grant, portrays a boy named Sylvester in order to help protect her father from fleeing England due to embezzlement charges in Sylvia Scarlett. Coincidentally, in a film the pair did in 1938, it was Grant’s turn to do a little cross-dressing himself in Bringing Up Baby.
Jamie Lee Curtis‘ dad Tony Curtis and his costar Jack Lemmon donned dresses and wigs in Some Like It Hot. In the film, they must go undercover after witnessing a crime and take jobs with an all-women band. All seems safe until one of them starts to get the hots for Sugar Kane Kowalczyk, played by costar Marilyn Monroe.
Comedian Milton Berle was also one of the first stand-up comedians of the time to embrace dressing in drag, as seen here on an episode of The Lucy-Desi Comedy Hour.
The most notorious cross-dressing role that comes to mind is Psycho, with Anthony Perkins dressing the part of his dead mother in that infamous shower scene. That creep factor alone is all we need for this decade!
Then of course, as the decade progressed, it brought Tim Curry‘s Doctor Frank-N-Furter, a “sweet transvestite from Transsexual, Transylvania” in The Rocky Horror Picture Show, which has since become a cult classic character and film. While many have portrayed the character since then, Curry truly did it best.
The ’70s can’t conclude without mentioning the most beloved drag icon on the list: Harris Glen Milstead, otherwise known as John Waters‘ muse, Divine. Best known for her roles in Pink Flamingos (1972) and Female Trouble (1974), both so controversial we can’t say more other than if you know, you know. But jumping to the early ’80s, 1981’s Polyester, which also starred ’50-’60s hunk icon Tab Hunter, had Divine playing a super overwhelmed housewife with tribulations that surely some “housewives” can deal with today, or not.
Even in the early ’80s, comedic greats Tom Hanks and Robin Williams dressed in drag for roles. Peter Scolari and Hanks pretend to be women to stay in a women’s boarding house after being kicked out of their apartment in the ’80s show Bosom Buddies. The show only went on for two seasons, and a little-know fact, Hanks first met his future wife Rita Wilson while she was on a guest appearance on the show.
The 1982 version of Victor/Victoria stars Julie Andrews as a struggling singer looking for work, who in the end trades genders with a male counterpart who just got fired and pretends to be her agent in hopes of finally getting a big part. Eventually, a love tangle ensues and the truth comes out that he is really a she. The first incarnation of this came out in 1933 in Germany as a musical comedy and again in 1935 with the name First a Girl.
Also in 1982, the film Tootsie starred Dustin Hoffman as a struggling actor who has a reputation for being hard to work with. He decides to dress himself as a woman in hopes to land a role, finds one on a trashy soap opera and eventually “becomes” the woman who he is portraying. That is until he falls for his costar, played by Jessica Lange, and her father falls for his character Dorothy. This film also stars Bill Murray and is Geena Davis‘ debut.
Of course, we weren’t done with Divine! In the 1988 film Hairspray, also by John Waters, Divine starred with Sonny Bono, Jerry Stiller, Deborah Harry and Ricki Lake, to name a few. Divine, who portrayed Edna, sadly died just three weeks after the film came out, making it her last film. In 2007, John Travolta took over the character.
The late ’80s also boasted more sketch comedy TV shows such as Kids in the Hall and some of the most infamous skits on Saturday Night Live, like “The Church Lady” with Dana Carvey or “Coffee Talk” with Mike Myers in the early ’90s.
In the ’90s, we see Robin Williams become the lovable Mrs. Doubtfire (1993), a role his character takes on, as a nanny in order to see his children while going through a bad divorce with his wife, played by Sally Field. This is one of the most beloved 1990s movies ever.
Just a few years after Mrs. Doubtfire, the Oscar-nominated The Birdcage (1996), also starring Robin Williams, followed the gay owners of a drag club called The Birdcage, who vowed to play it straight for their son’s soon-to-be wife’s ultra-conservative family. The film also starred Gene Hackman, Nathan Lane and Dianne Wiest.
Potentially the oddest grouping of actors to star in drag in the ’90s came in the 1995 film To Wong Foo, Thanks for Everything! Julie Newmar, which starred Patrick Swayze, Wesley Snipes and John Leguizamo as three drag queens traveling cross-country to make it to a pageant. Their car breaks down in small-town America, and they try to make the best of the situation with the townsfolk who have never witnessed anything of their kind. In the end, these three befriend the town, including the sheriff who was after them.
Before Tyler Perry put Madea on the map, Martin Lawrence came around with Big Momma’s House, which boasted a total of three films with Martin himself playing an undercover cop in the form of the loving matriarch of the family he is trying to protect.
Tyler Perry‘s Madea may be the most famous on this list in current culture. He puts on a curly wig and a sweater and becomes Madea Simmons, who has become so beloved that there are tons of films starring the feisty lady. You have Diary of a Mad Black Woman (2002), Madea’s Family Reunion (2006), Madea Goes to Jail (2009), Madea’s Big Happy Family (2011), Boo! A Madea Halloween (2016), A Madea Homecoming (2022) and TV’s House of Payne.
Lastly, Kinky Boots tells the true story of a struggling shoe factory owner who teams up with a drag queen named Lola (Chiwetel Ejiofor) to help save the business. He decides to create custom footwear for drag queens, causing a lot of controversy along the way and changing his own views in the process. The 2005 movie also inspired a Tony-winning Broadway musical.
Which character is your favorite on this list? What ones did we forget? (We know there are quite a few.) Let us know in the comments!