Cross-dressed to kill: movie/TV actors doing drag

Tyler Perry as Madea

By just putting on a curly gray wig and a granny sweater, Tyler Perry transformed himself into the feisty Madea Simmons and started a surprising sensation that has since grown to include a bevy of other projects, 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), and A Madea Homecoming (2022), as well as TV's House of Payne.

Monty Python

There's a long, grand tradition of cross-dressing in British drama that goes all the way back to Shakespeare, one this entirely male British comedy troupe continued. The Pythons famously wrote funny female parts, then—instead of getting women to play them—they donned frocks and makeup to play the roles themselves. A housecoat and a falsetto voice do wonders.

The cast of The Kids in the Hall (1989–95)

The Kids didn't dress as women for comedic effect necessarily—instead, they did it out of necessity! Since they played most of the parts themselves, and it was a male-heavy cast, cross-dressing became a hallmark of the show.

Jack Lemmon and Tony Curtis in Some Like It Hot (1959)

In this comedy classic, Jack Lemmon and Tony Curtis play two guys on the lam after witnessing a crime. They discover two jobs that'll take them out of town. The catch? The positions are with an all-women band leaving for a gig in Florida. What to do? Put on dresses and join the group, of course! And then, let the hijinks begin.

Flip Wilson on The Flip Wilson Show (1970–74)

The TV variety show star is best remembered for creating the role of Geraldine Jones, a spirited modern woman who had a boyfriend named Killer. Geraldine's signature line—"The devil made me do it"—became a national catchphrase.

Divine in Pink Flamingos (1972)

No one pulled off drag better than female impersonator Divine, who stars under the pseudonym ''Babs Johnson'' in this John Waters cult flick. And how great is it that she spends the film defending her title as "the filthiest person alive"?

Tim Curry in The Rocky Horror Picture Show (1975)

Huge pearls, frizzy hair, and lace-up vest, oh my! It doesn't get much better than Tim Curry's Dr. Frank N. Furter, who proclaims himself a "sweet transvestite from Transsexual, Transylvania" in this campy cult hit.

Tom Hanks and Peter Scolari in Bosom Buddies (1980–82)

Know what Tom Hanks was doing before he became the revered Academy Award-winning actor he is today? He was on TV in this cult buddy comedy that found him and Peter Scolari as two pals who—after being kicked out of their apartment building—pretended to be ladies so they could stay in a women's boarding house.

Dustin Hoffman in Tootsie (1982)

Can't land a job because you're difficult to work with? Do like Michael Dorsey (Dustin Hoffman)—er, should we say Dorothy Michaels?—in Tootsie: Just reinvent yourself instead and you might just land the job!

Divine in Hairspray (1988) and John Travolta in Hairspray (2007)

Drag superstar Divine made Edna Turnblad legendary with his gruff portrayal of the sheltered hausfrau in John Waters' original meditation on the civil rights movement in Baltimore. And taking on Edna for the movie (based on the musical, based on the movie), John Travolta reminded us just how light-on-his-feet he could be...even in a fat suit.

Martin Lawrence on Martin (1992–97)

Usually bedecked in a hideously clashing outfit and accompanying fanny pack, Martin's ridiculous and clueless across-the-hall neighbor Shenehneh was easily one of the best parts of this mid-'90s sitcom. Martin Lawrence played her to the max, in all her finger-waving glory.

Robin Williams in Mrs. Doubtfire (1993)

When Daniel Hillard (Robin Williams) loses custody of his kids after his wife (Sally Field) divorces him, he cooks up a plan to become their nanny. Presto—meet Euphegenia Doubtfire! Loved by the Hillard children, Daniel's nanny disguise fools everyone around him until nearly the end of the movie.

The cast of The Adventures of Priscilla, Queen of the Desert (1994)

The Australian comedy zeroes in on two friendly drag queens and a transgender woman who hit the outback in a huge bus they've lovingly named "Priscilla, Queen of the Desert."

Wesley Snipes, John Leguizamo, and Patrick Swayze in To Wong Foo, Thanks for Everything! Julie Newmar (1995)

More drag queens on road trips! This time, it's three New Yorkers—Noxeema (Wesley Snipes), Vida (Patrick Swayze), and Chi-Chi (John Leguizamo)—who set out for Hollywood to compete in a national drag queen contest. Like all good queens, they carry an autographed photo of their idol—former Catwoman Julie Newmar—around with them.

Nathan Lane in The Birdcage (1996)

Down in South Beach, there is a gay nightclub called the Birdcage, owned by Armand Goldman (Robin Williams) and his lover, Albert (Nathan Lane), who headlined as the fabulous "Starina."

Eddie Murphy in The Nutty Professor (1996)

Eddie Murphy dressed up for a total of seven roles—including most of the Klump family—in this remake. But his portrayal of the family's two matriarchs (Mama Klump and Grandma Klump) was especially hilarious and totally memorable.

John Cameron Mitchell in Hedwig and the Angry Inch (2001)

The things people do for love. After Hansel (John Cameron Mitchell) falls in love, he plans to leave communist East Germany for the West to marry his lover. But in order to get married, he undergoes an operation, so Hansel becomes Hedwig. The results aren't so great—hence the Angry Inch part of the movie's title—but Hedwig ultimately comes to embrace her genderqueer identity.

Marlon and Shawn Wayans in White Chicks (2004)

Not only did two of the Wayans brothers disguise themselves as women for this ridiculous send-up, but they also pretended to be the most ridiculous of white women.

Christopher Walken in Balls of Fury (2007)

Should Balls of Fury's Feng (Christopher Walken) actually be considered drag? That's debatable, but Walken's East Asian-inspired outfits in the ping-pong spoof comedy have a certain genderfluid style.