Director Ang Lee is back and helping us celebrate the fortieth anniversary of Woodstock with his newest film, Taking Woodstock. In addition to music, mayhem and mud, it features actor Liev Schreiber playing a tough, ex-Marine transvestite. Wearing a dress and heels wasn’t easy on the 240-pound actor, as Schreiber vented to People, “‘It was exhilaratingly humiliating…But I completely became giddy in a strange way the moment I put on the dress. Vanity quickly set in, and I thought to myself, ‘I wish my belly was flatter.’”
He also discovered that heels can be killer: “The shoes are awful,” says Schreiber. “But for a 6-foot-3-inch [tall] man, to walk around in stilettos is nearly impossible. But women have no idea what it’s like for a grown hairy man to remove all of his hair from his body. Now that hurts!” In honor of Schreiber suffering so for his art, we’ve compiled a list of our top ten favorite cross-dressers in cinematic history. Whether they’re men playing women, women playing men — or a woman playing a man playing a woman — all of these actors like it hot.
10. Johnny Depp, Ed Wood
It’s inevitable that, after seeing him play the STD-colony Jack Sparrow, audiences may have wondered if there was any way to make Johnny Depp not sexy. A guy with blades for fingers? Sign me up! Deranged serial-killing barber? Yes, please! But as this hilarious biopic proved, all you need to neuter Depp is a blond wig and a fuzzy sweater set, and suddenly he’s as appealing as your grandmother’s bridge partners.
9. Cillian Murphy, Breakfast on Pluto
When director Neil Jordan — known for the similarly gender-bending drama The Crying Game — cast Cillian Murphy — known for his roles in action and horror films — as the ’70s transvestite Kitten Braden, it might have seemed odd. And frankly, as Murphy plays her, Kitten does seem pretty whacked. But you have to admire her, at least for the guts it takes to wear the sequin-drenched squaw outfit she dons as part of a glam-rock band.
8. Gael Garcia Bernal, Bad Education
Undoubtedly the most dramatic and dark character on the list, Gael Garcia Bernal’s Juan — also known as Angel and Zahara — seduces, blackmails, and even kills his own brother in this neo-noir, all for the chance to make it big on the silver screen. Yes, he goes a tad overboard, but it seems like he just knows what all good drag queens do — go big, or go home.
7. Barbara Streisand, Yentl
Papa, can you hear her? The forty-one-year-old Streisand may have stretched credibility as a young girl passing for a young boy, but if you’re watching this film, you’re not here for realism. No, you’re here to see Streisand belt it out, and watch as Mandy Patinkin has a sexual identity crisis when he thinks he’s falling for a dude.
6. Julie Andrews, Victor/Victoria
It’s a testament to Julie Andrew’s acting ability that she can play a convincing man while wearing a gown. As the titular woman-playing-a-man-playing-a-woman, Andrews joins the list — with Streisand — of women who managed to make straight men question their sexuality. Oh, and they did it in their films, as well.
5. Jack Lemon and Tony Curtis, Some Like It Hot
As the oldest entry on this list, it’s surprising these characters ever made it to film in the first place, given the draconian rules of the Hayes Code, which were still somewhat in effect. And while no one could accuse Lemmon or Curtis of making the most attractive women, that doesn’t stop Curtis’ “Daphne” from bagging a millionaire fiancé by the film’s end.
4. Hugo Weaving, Priscilla Queen of the Dessert
Guy Pierce may have been the eye-candy in this cult hit from Australia, but the standout is Weaving as the level-headed Mitzi Del Bra. For those of you who only know Weaving as menacing Mr. Smith, you’re truly missing out — not just any actor can pull off both a sinister Matrix agent and a drag queen with an afro wig made of flowers with equal verve.
3. Gwyneth Paltrow, Shakespeare in Love
Before her documentary travelogue with Mario Batali, before GOOP, and before she named her son Apple — it seems so long ago, doesn’t it? — Gwyneth Paltrow was just another intriguing young actress. She was rewarded for this role with an Oscar, and if you find yourself losing your patience with Gwyneth as she rubs artisanal olive oil on antique tiles from Catalan, just remember — the girl can rock a pencil moustache.
2. Dustin Hoffman, Tootsie
She may not be the most glamorous gal on the list, but Dorothy Michaels is almost undoubtedly the most significant. In Tootsie, Hoffman played a young, difficult actor in desperate need of a job (are you listening, Bale?). He unwittingly created the role of a lifetime with the Dorothy Michaels persona, who became iconic and well-loved both onscreen and in real life. And who knew Hoffman could work a sequined gown?
1. John Cameron Mitchell, Hedwig and the Angry Inch
Hair like Farrah Fawcett, a voice like Marlene Dietrich, and an attitude like Johnny Rotten — is it any wonder that Cameron’s creation clawed and beat her way to the top of the list? Equally as capable of applying glitter eye shadow as putting a boot up your ass, Hedwig is the epitome of ferocity and theatricality that drag queens around the world aspire to.