TYLER PERRY AS MADEA
By just putting on a curly, gray wig and a granny sweater, 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), and Meet the Browns (2008), Madea Goes to Jail (2009), and Madea’s Big Happy Family (2011), as well as TV’s House of Payne.
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 was more than happy to continue. 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 does wonders.
British men are known for their propensity to dress like women, and Izzard is the poster-child of that phenomenon. He’s said before that he simply enjoys wearing make-up and clothing which society has deemed appropriate for women. ”Women wear what they want and so do I,” Izzard has remarked in the past.
THE CAST OF THE KIDS IN THE HALL (1989-1995)
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, male and female, themselves, and it was a male-heavy cast, the cross-dressing became a hallmark of the show.
FLIP WILSON IN THE FLIP WILSON SHOW (1970-74)
The TV variety show star is best remembered for creating the role of Geraldine Jones, a sassy, modern woman who had a boyfriend named Killer. Geraldine’s signature line — ”The devil made me do it” — became a national catchphrase.
JACK LEMMON & TONY CURTIS IN SOME LIKE IT HOT (1959)
Simply put, this cross-dressing fest is a comedy classic. Lemmon and 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-girl 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.
DIVINE IN PINK FLAMINGOS (1972)
No one pulled off the man-as-woman thing 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 Dr. Frank N. Furter, who proclaims himself a ”sweet transvestite from Transsexual, Transylvania” in this freakish cult hit.
TOM HANKS & PETER SCOLARI IN BOSOM BUDDIES (1980)
Know what Hanks was doing before he became the revered Academy Award-winning actor he is today? He was dragging around on TV in this cult buddy comedy that found him and Scolari as two pals who, after being kicked out of their apartment building, dressed as ladies so they could stay in an all-girls boarding house.
DUSTIN HOFFMAN IN TOOTSIE (1982)
Can’t land a job because you’re difficult to work with? Do like Michael Dorsey (Hoffman) — err, should we say Dorothy Michaels? — in Tootsie: Just dress as the opposite sex instead and you might just land the job!
DIVINE IN HAIRSPRAY (1988) & JOHN TRAVOLTA IN HAIRSPRAY (2007)
Drag superstar Divine made Edna Turnblad legendary with his gruff portrayal of the over-sized housfrau 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 IN MARTIN (1992-1997)
Usually bedecked in a hideously clashing outfit and accompanying fannypack, Martin’s ridiculous and clueless across-the-hall neighbor Shenehneh was easily one of the best parts of this mid-’90s sitcom. Lawrence played her to the max, in all her finger-waving and ghetto-ized glory.
ROBIN WILLIAMS IN MRS. DOUBTFIRE (1993)
When Daniel Hillard (Williams) loses custody of his kids after divorcing his wife (Sally Field), he cooks up a plan to become their nanny. Presto — meet Euphegenia Doubtfire! Loved by the Hillard children as the portly nanny with a somewhat manly gait, Mrs. Doubtfire fooled 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 three friendly drag queens (two gay men and a transsexual woman) who hit the outback in a huge bus they’ve lovingly named ”Priscilla, Queen of the Desert.”
WESLEY SNIPES, JOHN LEGUIZAMO, & PATRICK SWAYZE IN TO WONG FOO, THANKS FOR EVERYTHING, JULIE NEWMAR (1995)
More drag queens on road trips! This time, it’s three New York drag queens — Noxeema (Snipes), Vida (Swayze), and Chi-Chi (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 was a gay nightclub called The Birdcage, owned by Armand Goldman (Robin Williams) and his lover, the divine Albert (Lane), who headlined as the fabulous ”Starina.”
EDDIE MURPHY IN THE NUTTY PROFESSOR (1996)
Murphy dressed up for a total of seven roles — including most of the over-sized Klump family — in this remake. But his portrayal of the family’s two matriarchs (that’d be 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 (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 a sex change, so Hansel becomes Hedwig. The results aren’t so great, though, hence the Angry Inch part of the movie’s title.
MARLON & SHAWN WAYANS IN WHITE CHICKS (2004)
Not only did two of the Wayans brothers go lady for this ridiculous send-up, they also turned themselves into the most ridiculous of white ladies. Extra points to the pair for taking down silly socialites (looking at you, Paris and Nikki!) along the way.
CHRISTOPHER WALKEN IN BALLS OF FURY (2007)
Should Balls of Fury‘s Feng (Walken) actually be considered drag? That’s debatable, but Walken’s outlandish, Asian-inspired outfits in the ping-pong spoof comedy certainly had shades of man-dressing-as-a-woman style.