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See some of our favorite cross-dressing characters in pop culture history

Shaun Harrison
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1 of 22 Eric McCandless

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ABC's Work It follows the misadventures of two guys who dress as women to get jobs as pharmaceutical reps. (In these economic times, women are taking over the workforce... or so says one of the show's characters. Hmmm.) The good news is doing drag can — and has been — a lot more interesting through the years, not to mention fun! Peruse our favorite cross-dressing characters from pop culture history, from Mrs. Doubtfire to Rudy Giuliani.
2 of 22 CBS/Landov

Jamie Farr on M*A*S*H

Hollywood has come up with a lot of reasons for characters to dress in drag, but none was as topical — or hilarious — as Klinger's: He habitually wears women's clothing in an attempt to obtain a Section 8 psychiatric discharge from the Army. In later episodes, he sheds his dresses and is promoted to sergeant.
3 of 22 New Line Cinema

John Travolta in Hairspray

Tracy's insecure mom, Edna, has always been played by a man in drag, but despite his musical success in Grease, few expected Travolta to trade in his T-Birds jacket for a muumuu. The star took the role far beyond stunt casting and showed surprising heart and humor in the over-the-top role.
4 of 22 Lionsgate

Tyler Perry as Madea

Halleluyer! Tyler Perry's 6-foot-5-inch frame is the perfect canvas on which to build this loud, angry, mountain of a Southern black woman. Though Madea is usually played for laughs, her worldwise ways almost always impart an important lesson. First appearing in Perry's plays, Madea has appeared in 13 of the actor-director's films, as well as his three television series. Whether she's in jail, hosting a family reunion, or feeding her neighbor's noisy dog sleeping pills, she's always a hoot.
5 of 22 20th Century Fox/Kobal Collection

Tim Curry in The Rocky Horror Picture Show

Dr. Frank-N-Furter may just be a "Sweet Transvestite" from Transsexual, Transylvania, but he also singlehandedly revolutionized cross-dressing — seamlessly meshing rock 'n' roll with, well, mesh. The good doctor’s get-up — which includes fishnets, a leather corset, killer pumps and not much else — goes a long way in furthering the film’s message of individualism. It must be said: No man has ever looked hotter in drag.
6 of 22 Miramax/Everett Collection

Jaye Davidson in The Crying Game

The clever marketing for this 1992 indie film urges moviegoers not to reveal "the big secret." It starts out charmingly enough. Fergus, a mealy-mouthed IRA terrorist (Stephen Rea), falls in love with Dil, a seductive lounge singer (Davidson). But soon enough he discovers that his stage beauty has a winkie! It's to the film's credit that though the pair do not remain an item, a modicum of understanding passes between them. Davidson even nabbed a Best Supporting Actor Oscar nomination for the role.
7 of 22 Paramount

Anthony Perkins in Psycho

"Mother!" Norman Bates comes across as a harmless momma's boy in Alfred Hitchcock's 1960 thriller — until it turns out that he's channeling mom (who's a skeleton in the basement) and dressing like her. Even scarier than Perkins in a wig and dress was the knife he wielded. What he did to Janet Leigh in the shower terrified women so much that they opted for baths long after seeing the film.
8 of 22 20th Century Fox/Kobal Collection

Robin Williams in Mrs. Doubtfire

After a divorce makes it impossible for Daniel (Williams) to see his three kids regularly, he does drag out of desperation. And as 60-year-old nanny-for-hire Euphegenia Doubtfire, Williams gets to be plenty theatrical, setting her fake boobs on fire while cooking, drunkenly losing her dentures in a glass of champagne and adopting a muddled (but still somehow convincing) British (Scottish?) accent.
9 of 22 Summ/Triton/Kobal Collection

Joyce Hyser in Just One of the Guys

College journalist Terry Griffith (Hyser) goes undercover as a high school football player to combat her professor's overt sexism. In the oddest romantic comedy of 1985, Terry fends off both a bully and a female admirer, all the while falling in love with one of her teammates.
10 of 22 Warner Bros./Everett Collection

Kathleen Turner on Friends

As Charles Bing, Oscar nominee Turner plays Chandler's cross-dressing dad — yes, dad. When Monica wants to meet her future father-in-law, she and Chandler go to Las Vegas to catch his/her cabaret act (his stage name is Helena Handbasket), which includes a rousing, partially clothed rendition of "It's Raining Men." Can Chandler be any more embarrassed?
11 of 22 Wayans Brothers/Revolution Studios/Kobal Collection

Shawn and Marlon Wayans in White Chicks

The only thing more difficult than convincing gender-bending is race-and-gender-bending. FBI agents and brothers Kevin (Shawn Wayans) and Marcus (Marlon Wayans) disguise themselves as the privileged white heiresses they're tasked with protecting. In the process, they get caught up in all sorts of white-chick activities — like car-singing Vanessa Carlton's "A Thousand Miles". It's hilarious, yes, but we much prefer Terry Crews' non-drag, head-shaking and totally on-pitch rendition. Turns out "A Thousand Miles" is a black guy's jam too.
12 of 22 Kobal Collection

Tom Hanks and Peter Scolari on Bosom Buddies

What are ad men Kip Wilson (Hanks) and Henry Desmond (Scolari) to do when their apartment building is demolished? Dress as women in order to get a dirt-cheap room at the women-only Susan B. Anthony hotel, of course! With the help of a co-worker who also lives at the hotel, "Buffy" and "Hildegarde" fool the hotel manager, as well as the residents, including Kip's love interest. But once the series abandons the dudes-in-drag concept at the beginning of the second season, the show declines and is canceled. We think it's pretty clear what the moral of this story is.
13 of 22 Columbia/The Kobal Collection

Dustin Hoffman in Tootsie

Before Sarah Palin and Sally Jessy Raphael, Dustin Hoffman made women's eyewear sexy playing out-of-work actor Michael Dorsey. By donning a wig, a snazzy blouse and said spectacles, he masquerades as no-nonsense actress Dorothy Michaels, and lands the female lead in a soap opera. Not only is he/she more successful as a woman, but he has more than his/her share of love interests... of both sexes. "I was a better man with you as a woman than I ever was with a woman as a man," he tells a baffled but bewitched Jessica Lange. America in 1982 was similarly smitten, earning the film 10 Academy Awards, including one for Lange.
14 of 22 Everett Collection

Nathan Lane and Gene Hackman in The Birdcage

It's a simple story really: Boy meets girl. Boy makes gay dad's lover dress in drag and pose as his mom to impress girl's parents. Lane plays a hilarious drag queen opposite love interest Robin Williams, but viewers don't expect conservative Senator Keeley (Hackman) to get into the act as well to hide from the media. It's this meeting of the left and right, the expected and unexpected, that makes this progressive comedy so memorable.
15 of 22 20th Century Fox

Martin Lawrence in Big Momma's House

After Eddie Murphy did it in The Nutty Professor, it became all the rage to dress up in a fat suit as a woman, which is why it was no surprise that Lawrence used that same shtick in Big Momma as an FBI agent going undercover. The only thing more uncomfortable than the "flashlight" in Nia Long's back when they shared a bed was that it spawned two sequels.
16 of 22 Univeral/Amblin/Kobal Collection

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Patrick Swayze, Wesley Snipes and John Leguizamo in To Wong Foo, Thanks for Everything! Julie Newmar At this point in his career, Swayze had really done it all, so why not play a drag queen who sets out on a road trip to Hollywood with his "gal pals" to compete in a national drag queen pageant. Of course, their car had to break down in a racist, homophobic backwater town, where they're forced to teach the town a thing or two about tolerance. (And yes, Julie Newmar is actually in the movie.)
17 of 22 Miramax

Gwyneth Paltrow in Shakespeare in Love

What's better than Gwyneth Paltrow playing British (Sliding Doors) or British and historical (Emma)? Paltrow playing British, historical... and a guy! In the period rom-com, wannabe actress Viola (Paltrow) must pretend to be "Thomas Kent" to enter the strictly male profession of acting and land a part in a new play by William Shakespeare's (Joseph Fiennes), Romeo & Juliet. As the film's title indicates, he falls for the real her, but alas, theirs is a star-crossed love as well. The movie won seven Oscars, including one for Best Picture and Best Actress, paving the way for Goop and at least one Emmy-winning Glee guest-starring role.
18 of 22 Logo Tv

RuPaul on RuPaul’s Drag Race

To some, cross-dressing is a hobby, but to RuPaul Charles, it's a fierce competition where contestants compete for to be crowned "America's next drag superstar." In RuPaul's Drag Race, Charles tells contestants flat out: "To win this competition, you're going to have to be hotter than Tyra Banks wearing a fat suit on the Fourth of July!" That's hot. (He's also a successful recording artist. Remember "Supermodel"? You better work!)
19 of 22 NBC

Rudy Giuliani on Saturday Night Live

In a Saturday Night Live Thanksgiving skit, Italian grandmother Mrs. Silvestri sits at a kitchen table stuffing manicotti while complaining to her daughter Rita. The role-playing is so authentic, it's hard to believe that former Mayor Rudy Giuliani is behind the rotund "lady" sporting silver hair, knee-high pantyhose, orthopedic shoes, and a floral muumuu.
20 of 22 Kobal Collection

Julie Andrews in Victor/Victoria

Stay with us on this one. In husband Blake Edwards' musical comedy, Julie Andrews plays Victoria, who poses as a man who then dresses as a woman in a drag show. Romantic complications ensue, of course, when the nightclub owner falls for him, er, her. It takes a real woman to play a woman playing a man playing a woman.
21 of 22 Fox

David Cross on Arrested Development

When Tobias dons his best housekeeping outfit and introduces himself as Mrs. Featherbottom, he tries to convince us that he's as good of an actor as Robin Williams was in Mrs. Doubtfire. But too bad for Tobias, no one is fooled by the man inside.
22 of 22 Everett Collection

Jack Lemmon and Tony Curtis in Some Like It Hot

Two musicians go on the lam after witnessing the St. Valentine's Day Massacre in Billy Wilder's classic 1959 comedy. The best way to get out of town? Dress as women and join an all-girls orchestra — which includes one member played by Marilyn Monroe. Both guys stumble in high heels, and both find love — although it's to the chagrin of Lemmon's character. When he reveals his true gender to his millionaire suitor, he responds, "Well, nobody's perfect!"