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F. Scott Fitzgerald in a Dress, James Franco in ‘Candy’ & More Cross-Dressing Stars

Long before Kanye wore skirts, F. Scott Fitzgerald donned a dress for a Princeton musical-comedy troupe. From James Franco on the cover of Candy to Tom Hanks in the 1980s classic Bosom Buddies, see more celebrities who have shown some leg.

Long before Kanye wore skirts, F. Scott Fitzgerald donned a dress for a Princeton musical-comedy troupe. From James Franco on the cover of Candy to Tom Hanks in the 1980s classic Bosom Buddies, see more celebrities who have shown some leg.

F. Scott Fitzgerald

Years before he wrote The Great Gatsby, F. Scott Fitzgerald made an awfully good Daisy Buchanan. In a photograph taken in 1916, while he was still attending Princeton, Fitzgerald posed as a woman for an ad promoting The Evil Eye, a musical he co-wrote and performed in with the Princeton Triangle Club. Reviewing his performance, The New York Times said Fitzgerald was the production’s “most beautiful show girl.”

James Franco

This ought to open up several creative-casting options: James Franco appears in drag on the cover of the latest Candy magazine, “the first fashion magazine ever completely dedicated to celebrating transvestism, transexuality, cross dressing and androgyny, in all its manifestations.” He was shot by fashion photographer Terry Richardson in blue-eye shadow and red lipstick with jewelry and slicked-back hair.

Kevin Mazur, WireImage / Getty Images

Sting

At an annual benefit concert last May for The Rainforest Fund, Sting managed to find a way to upstage Elton John: the singer performed with “a flowered hat, dangling earrings and a glittery necklace” when he took the stage with John (himself decked out in a boa) and Shirley Bassey. The 1980s-themed benefit also featured Lady Gaga, Bruce Springsteen, and Debbie Harry, and Sting later ditched the costume for a duet with Gaga on “Stand By Me.”

Courtesy of Everett Collection

Johnny Depp

Long before he played flamboyant Captain Jack Sparrow in the Pirates of the Caribbean franchise, Johnny Depp got in touch with his feminine side in two movies: 1994’s Ed Wood and 2000’s Before Night Falls. But for Depp, two gender-bending performances apparently weren’t enough. Last year, he told The Daily Mirror that he’s still itching to play female roles: “My dream would be to play musical legend Carol Channing in a biopic of her life,” he said, adding that he’d even “have a go at playing a 12-year-old girl if they asked me to.”

Jude Law

Jude Law showed his softer side for the 2009 film Rage, playing a brunette supermodel named Minx. Though the movie didn’t get much exposure—it was released straight to DVD—Law certainly turned heads in his role. Said director Sally Potter of her star, “The more he became a ‘she,’ coiffed and made-up—the more naked was his performance. It was an extraordinarily intense part of the shoot.”

Adam Lambert

As a popular contestant on American Idol’s eighth season, Adam Lambert became well-known for bringing his glam, sexually ambiguous onstage persona to the normally tame and family-friendly Fox show. He stirred up even more controversy when, during his run on Idol in the spring of 2009, old pictures of him in drag surfaced online. Lambert casually brushed off the pictures in an interview with People magazine, saying, “I’ve only dressed in drag three or four times. That’s not me.” Viewers brushed it off, too—Lambert ended the season as runner-up to winner Kris Allen.

Sony Pictures Classics / Courtesy Everett Collection

Gael Garcia Bernal

In 2004, Mexican actor Gael Garcia Bernal hit the Cannes Film Festival to promote two films, and it wasn’t only his portrayal of Marxist revolutionary Che Guevara in The Motorcycle Diaries that raised eyebrows. Garcia Bernal was also there to support Bad Education, in which he played three different characters—including a transvestite named Zahara. Though the role was certainly challenging, he told The Independent that suiting up in drag has its perks. “Oh, it was very liberating,” he said. “As a girl, you can get men to do anything you want them to do—if you do it intelligently enough.”

20th Century Fox / Courtesy of Everett Collection

Robin Williams

Robin Williams famously didn’t crossdress in The Birdcage but his turn as a plump British nanny in Mrs. Doubtfire made the movie a box office smash. For Birdcage, Williams told director Mike Nichols that he wanted to try something different than his usual flamboyant characters. Nichols agreed and cast him opposite Nathan Lane’s drag diva.

Columbia Pictures / Courtesy Everett Collection

Shawn and Marlon Wayans

Although they thought it seemed like a funny idea at the time, apparently Shawn and Marlon Wayans had no idea what they were getting into when they came up with the idea of playing FBI agents posing as blond, blue-eyed girls. They spent seven hours a day in makeup, applying foam masks, acrylic paint and contact lenses that were so painful, ''they should be the s---- that they use over in Iraq to get information out of al-Qaeda,'' Shawn said of their Hilton sister wannabes. But despite the discomfort, would the boys do it again? Apparently, as a White Chicks sequel was announced in August 2009. "I make one hell of a sexy white woman, if I do say so myself,'' Marlon said. ''I might not be an impressive black man, but as a white woman, I'm something else!''

Courtesy Everett Collection

Tom Hanks

Before he was taking home Academy Awards, Tom Hanks got in touch with his feminine side on the classic 1980s series Bosom Buddies. The show featured Hanks and Peter Scolari as two men cross-dressing in order to live in a female-only apartment building – when in costume, Hanks’ character went by the name “Buffy.” Though the show was never a major ratings or critical success, Hanks has embraced the panty hose in his past and reunited with the cast in April for the TV Land Awards and said, “You can look back and say, ‘You know, we really did some great shows.’” Still, Scolari and Hanks were less fond of their elaborate drag costumes: “We would tell the writers, ‘Aren’t we strong enough as clever guys with our banter? Isn’t that enough?’ And then there would be the next episode and we’d have to dress up,” said Hanks.

Courtesy of Everett Collection

John Leguizamo, Wesley Snipes, and Patrick Swayze

It’s hard to imagine three more macho actors in drag than Patrick Swayze, Wesley Snipes and John Leguizamo, which is part of the charm of To Wong Foo, Thanks For Everything! Julie Newmar." How did the actors feel about dressing up as women? “I ain't waxing that stuff again," Swayze at the time. But at least they agreed on one thing. "I was the finest," John Leguizamo said. "You looked so good. You were sweet, sugar!" Snipes admitted.

Tony Curtis and Jack Lemmon

Masquerading as “Josephine” and “Daphne” to throw the mob off their trail, Tony Curtis and Jack Lemmon set the gold standard for Hollywood drag in the 1959 classic Some Like It Hot. Curtis later chronicled his experiences on the film in two books, The Making of Some Like it Hot and his memoir, American Prince. He wrote that he initially worried about taking the part "after years of putting up with guys coming on to me," but spending his days on-set dressed as a woman didn’t prove to be an impediment for Curtis, who carried on an affair with co-star Marilyn Monroe throughout filming.

Sony Pictures / Courtesy Everett Collection

Cillian Murphy

Pushing back against his burgeoning image as a heartthrob, Cillian Murphy chose an unexpected follow-up to his breakout roles in Batman Begins and 28 Days Later, playing a transvestite named “Kitten” in the 2006 film Breakfast on Pluto. To prepare for the role Murphy spent nights out on the town with a group of Irish transvestites and also picked up tips from Gael Garcia Bernal, who was fresh off his role as “Zahara” in Bad Education. “He told me, ‘Wax, don’t pluck,’” said Murphy. “But I plucked.”

Courtesy Everett Collection

Dustin Hoffman

''We did two months of tests with him,'' director Sydney Pollack said of working with Dustin Hoffman before shooting the 1982 hit Tootsie. ''We shaved his legs, his arms and the backs of his fingers. We designed a wardrobe full of high necklines and scarves at the throat, because he's got a size 16 1/2 neck and a big Adam's apple. We consulted a female impersonator about his figure… He's got to wear a latex-base makeup that's murder on his skin and only lasts for a few hours. It's been a nightmare trying to keep him looking like a woman.” Pollack said the fact that his film—about an unemployed actor who dresses as a woman to get more work—was made near the same time as Yentl and Victor/Victoria clearly had something to do with the women’s movement and a reevaluation of sex roles. Hoffman noted his infant son might be confused seeing daddy put on a dress every day, but, “Luckily we can afford therapy for him later.”

AP Photo

Bugs Bunny

Bugs Bunny wore women's clothes in dozens of Looney Tunes shorts—apparently lipstick and a skirt was enough to trick Elmer Fudd countless times. "Sex in the Warner toons was more likely to be transgressive and connected to deception, especially cross-dressing," Billy Collins wrote in The Wall Street Journal. "Bugs is quick to put on a frock and kiss Elmer on the mouth but only for the purpose of fooling his perennial victim. Disney-romance led to marriage. Warner Brothers-romance was linked to guile and aimed at redress." Click here for a transfixing montage of Bugs' dabbling in gender play.