Drag in Film: Cross Dressing Movies Through the Decades
Long before Dustin Hoffman was nominated for an Oscar for his role as Tootise, or RuPaul and his series RuPaul’s Drag Race put the art of drag at the forefront of pop culture, drag existed as a popular form of entertainment. In fact, drag pops up in some of the earliest films ever made, and has developed alongside film and TV in popular culture.
Let’s dig in and check out the history of drag and cross-dressing in film.
1910s-1940s
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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.
Everett Collection
Fast forward to 1935: 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 1938, it was Grant’s turn to do a little cross-dressing himself, in the pair’s film Bringing Up Baby.
1950s
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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.
1960s
via MovieStillsDB
The most notorious drag role of all time may be Psycho, with Anthony Perkins dressing the part of his dead mother in that infamous shower scene. However, we must throw out an honorable mention to Blake Edwards’ High Time which has Bing Crosby dressed as a Southern Belle for a frat initiation.
1970s
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In the ’70s, Flip Wilson on The Flip Wilson Show created the character Geraldine Jones, who often said, “The devil made me do it.” You said that catchphrase at least once in the ’70s, didn’t you?
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 be discussed 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 films so controversial, we can’t say more other than if you know, you know. But by 1981’s Polyester, which also starred ’50-’60s hunk icon Tab Hunter, Divine was playing more traditional roles, portraying a super overwhelmed housewife with tribulations that surely some “housewives” can deal with today.
1980s
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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. Though it’s famous as the place where Hanks got his start, the show only went on for two seasons (a little-know fact, Hanks first met his future wife Rita Wilson while she was a guest actor on the show).
MGM/ Courtesy Everett Collection
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 triangle ensues and the truth comes out. The first incarnation of this story came out in 1933 in Germany as a musical comedy and again in 1935 with the name First a Girl.
Columbia Pictures/courtesy Everett Collection
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.
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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. In 2007, John Travolta took over the character in the musical adaptation of the film.
The late ’80s also boasted more drag in 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.
1990s
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In the ’90s, Robin Williams became the lovable Mrs. Doubtfire (1993), a nanny that his character pretends to be in order to see his children while going through a bad divorce from his wife, played by Sally Field.
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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.
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In 1996, Eddie Murphy played seven —yes, SEVEN! — characters in The Nutty Professor remake, including Mama Klump and Grandma Klump. If you’ve seen this one, you can’t forget the iconic dinner scene.
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Potentially the oddest grouping of actors to do drag in the ’90s came together in the 1995 film To Wong Foo, Thanks for Everything! Julie Newmar. The film 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’s resident, including the sheriff who was initially after the group.
2000s
20th Century Fox Film Corp./Everett Collection
Before Tyler Perry put Madea on the map, Martin Lawrence came around with Big Momma’s House, a film that stars Lawrence himself playing a cop who goes undercover as the loving matriarch of the family he is trying to protect. The movie got two sequels!
Columbia Pictures/Everett Collection
In a movie that is so bad it is good, the Wayan brothers, Marlon and Shawn, became white women in White Chicks — again, as cops working to protect two rich women from getting kidnapped.
Lions Gate/Everett Collection
Tyler Perry‘s Madea may be the most famous drag character in our culture today. Perry puts on a curly wig and a sweater and becomes Madea Simmons, who has starred in hit films including 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.
Buena Vista Pictures/Everett Collection
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!
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March 2021
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