Gender-Bending Stars: Your Favorite Celebs Dressed In Drag

There are a number of celebrities who have dressed up as the opposite sex, whether for a role, event, or photo shoot. While sometimes it’s for comedic purposes or shock value, other times it’s to make a heartfelt statement. whatever the case, it’s always fun to see some of our favorite stars dressed in drag. Which ones do you think nailed it?

My First Day As A Woman, And I’m Getting Hot Flashes

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There’s no doubt that the 1993 comedy Mrs. Doubtfire was a smash hit thanks to Robin Williams’ hilarious portrayal of a female housekeeper who infiltrates the home of his ex-wife in order to spend time with his children. He may not have made the most attractive woman, but he still managed to be believable, and more importantly, lovable. Fans fell in love with the character. While it was not the first mainstream film to portray a man in drag, it was one of the first hit family films to do so and paved the way for a number of films to follow.

Do you remember Angelina Jolie’s transformation in Salt?

Fishnets, High Heels, and Broadway

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It was difficult to even recognize Neil Patrick Harris during his portrayal of Hedwig, an East German transgender glam rock singer, in off-Broadway’s Hedwig and the Angry Inch. The decision to play Hedwig was not an easy one for Harris. He’d come out eight years prior, and dressing in drag was something he’d never even considered. “I’m not a super effete person, and I have to turn into that, and in doing so it brings up a lot of homophobic insecurities within myself,” says Harris. Those insecurities seemed to be completely masked during the shows, and both fans and critics alike praised Harris’ performance.

Changing Our View On The Sexes

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The 1982 film Tootsie is considered the first super successful, mainstream “feminist film,” and is accredited with having an impact on the way the opposites sexes view each other. The role also had a major impact on Dustin Hoffman, who played Tootsie. He was nominated for an Oscar and was praised for his comedic performance, but for Hoffman, the film wasn’t a comedy. He was shocked by the fact that once he was all made up in drag, he was not an attractive woman because he expected he would be. This made him realize just how much women are judged solely based on their physical appearance.

Scene Stealer

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While Johnny Depp may have only been onscreen for a few minutes in Before Night Falls, his portrayal as the flamboyant transvestite Bon Bon, in red lipstick and high heels, is one of the highlights of the film. Many critics and fans were mesmerized by his performance, and called his moments in the film “scene-stealing.” He plays a prison warden in the film as well, but his acting chops run so deep that your brain barely registers that it is the same person. Not to mention he doesn’t look half bad as a woman.

Cover Boy/Girl

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Jared Leto won an Oscar for his portrayal of a transvestite diagnosed with HIV in the film Dallas Buyers Club. Candy Magazine, the world’s “first transversal style magazine” then featured Leto on the cover… in drag. He looked amazing and quite comfortable both onscreen and in the photoshoot. After his win, he revealed that he was seriously considering wearing drag to the Oscars, but in the end, decided against it. According to Leto, “It’s a lot, what women have to do to themselves. But in the end, when you put that final dash of lipstick on and your look all comes together, it really is a glorious reward.”

Mommy, Is That You?

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When Brad Pitt went to visit his then-wife, Angelina Jolie, on the set of her film Salt, he happened to arrive while she was midway into her drag transformation as a military officer. He was totally creeped out by her half-man-half-woman appearance. Once in full transformation, the stunning actress was almost unrecognizable and looked just like a real man. Her look was so convincing that she even decided to prank her son Maddox, who was eight at the time. She showed up at home dressed like the character, and he at first didn’t even know it was her until she used her real voice.

Wait until you read what John Travolta learned about being a woman on the set of Hairspray.

Dude Looks Like A Lady

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In 1993, before Goerge Clooney was the A-list heartthrob he is today, he starred in a film called The Harvest. Clooney appeared in the film very briefly as a lip-synching transvestite in a club scene, wearing a blonde Farah Faucet style wig, a sparkling gold sequin bra, and hot pants. If you didn’t already know that it was him in the role, you may not even recognize the actor. The jawline and hairy stomach don’t make him the most conventionally attractive of women, but he definitely gets into the role. His cousin, Miguel Ferrer, directed the film, so perhaps that’s why Clooney agreed to do it.

Breakout Performance

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Lee Pace nailed the role of Calpernia Addams, a transgender performer who falls in love with a soldier, in the true-story film Soldier’s Girl. He looked so believable that people started to speculate if the silicone prosthetics were actually real breasts. The real Calpernia has even stated that Pace’s performance was very accurate. Pace admitted that going into the role was a bit scary, but he was fascinated with the story and up for the challenge. He was, however, nervous about what his father would think at the time. Considering he was nominated for a Golden Globe for his first ever film, he was probably proud.

She-Bond

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James Bond actor Daniel Craig decided to show his support for equality between the sexes by dressing in drag. In celebration of International Women’s Day 2011, Craig decided to put himself in women’s shoes, literally. During a short two-minute film commissioned by EQUALS, which features the voice of Dame Judi Dench as the character M, Craig appears as Bond, and M asks him whether or not they’re equals. She then lists all the discrimination and hardships women experience and asks if he’s ever considered what it’s like to be one. Craig then reappears onscreen as a woman, with a long blonde wig, dress, make-up and high heels.

A Dream Come True

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In Albert Nobbs, Glenn Close plays a woman who pretends to be a man in order to join Ireland’s workforce in the 1800s. Close donned drag nearly 30 years prior, in the same role, for an off-Broadway production of the story. For years she had been working towards making the story a feature film, She was so happy it was coming to fruition that she cried when she first saw herself dressed as the character. Aside from her clothing and hair, she’s believable as a man because of her mannerisms and body language. Close admitted that playing Hobbs was the challenge of her career.

Psychological Leap

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With his extremely masculine features, it’s hard to picture actor Sean Bean in drag, but he manages to blow it out of the park as the transvestite teacher Tracie/Simon in BBC’ series The Accused. Fans and critics alike were floored by his performance, despite the fact he wasn’t the most physically attractive woman. Bean was nervous playing the role, as he never even imagined he’d play a transvestite character. According to Bean, “Psychologically, it was quite a leap. A big leap. That takes some time to get to – it wasn’t just… bang, switch it on. You can’t just suddenly turn yourself into a character like that.”

Heavy Lifting

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John Travolta’s career has been filled with a wide array of characters, from a dancing teen heartthrob to an action hero, and he’s picked up two Oscars along the way. So it wasn’t too shocking to see him play Edna Turnblad, an overweight, overprotective mother, in 2007’s Hairspray, though it took him two months to agree to do it. He then spent five hours a day encased in a 30-pound body suit. He joked about the attention he got on set, “Men were flirting with me and I was being given power I never had before. I found it fascinating. Women have power I didn’t know they had.”

Keep reading to see why Jude Law is attractive no matter what he does.

Second Time Around

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“It was exhilaratingly humiliating,” is how Liev Schreiber describes his role of an ex-Marine transvestite in Taking Woodstock. At first, he feltself-conscious, wishing that his stomach was flatter and he had more attractive legs. Despite his insecurities, fans and critics felt he was believable. His wife Naomi Watts, on the other hand, was initially horrified when she first saw him. Schreiber admitted that shaving his body was awful and that he had a really hard time walking in stilettos. But this wasn’t the first time he dressed in drag…he dressed as a woman for the 1994 comedy Mixed Nuts.

Embracing The Culture

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James Franco has openly explored his sexual identity through his roles and has no problem embracing the gay and transgender culture. So when Candy magazine approached him about doing a cover and spread in their fall-winter 2010-2011 issue, he happily went for it, complete with cherry red lipstick, heavy eyeshadow, and fake eyelashes. He appears to be completely at ease, posing fiercely in all his shots, and makes a pretty good looking woman. His actions have sparked a lot of controversy to his sexual orientation, but Franco claims he has chosen his sexuality bending roles because they are more interesting.

Surprise Performance

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Annie Lennox was pretty courageous by dressing in drag during a time that it was still very taboo. She performed at the 1984 Grammy Awards dressed as a very believable man. She explains, “There had been quite a controversy about my gender and so just to really push the envelope I took it on myself to shake them up a bit. I got a man’s suit and I had makeup stubble. When I got to the stage to perform, the stage manager was totally freaked out because he couldn’t see me. He didn’t realize who I was. When the curtain came up, you could almost hear the audience inhale.”

Supreme Drag Queen

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In the 1995 film To Wong Foo, Thanks for Everything! Julie Newmar,two very masculine actors dressed up as drag queens for the leading roles: Patrick Swayze and Wesley Snipes. John Leguizamo was the third main character and was a pretty believable woman. While Snipes’ performance was great, visually, him as a woman was quite jarring. Swayze, on the other hand, seemed to be natural, evident in the opening scene. the scene starts with Swayze as a man, and then he elegantly transforms into his alter ego. It was a pretty shocking move for him, considering the times, and his filmography up to that point.

Tears Shed

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Hilary Swank won an Oscar for her portrayal of Brandon Teena in 1999’s Boys Don’t Cry. It told the real-life story of Teena, a transgender man who was raped and murdered by his male acquaintances after they discovered he was born a female. To prepare, Swank spent a month living as a man in her private life, even convincing her neighbors that she was actually her brother visiting. Aside from them, she found most people’s reaction to her pretty disturbing. ”People don’t want to have anything to do with you, and it put me in a state of real hopelessness. I cried a lot for days.”

Supermodel Good Looks

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Jude Law looks beautifully feminine as a transgender Eastern European supermodel named Minx in the 2009 film Rage. His performance was intense and extremely believable. The first time he transformed, it took a few hours because he had to remove all of his hair. “I’m a bit of a coward,” said Law. “I didn’t go for the waxing. I just shaved it.” Makeup had to be used to cover his tattoos and stubble. We know Jude Law is pretty as a man, but as a woman, he’s so attractive that’s he’s perfectly convincing as a super successful runway model.

Breaking Boundaries

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During a time when trans characters were just not being portrayed on popular TV shows, David Duchovny pushed boundaries by appearing as the transgender character Dennise Bryson in Twin Peaks. Denise emphasized to those who knew her prior to her transformation to call her by the appropriate pronoun, she, a topic that was not as openly discussed at the time as it is now. They approached the whole issue of acceptance quite sensitively for the time. Though his look is now outdated, it was very era-appropriate, and Duchovny was amazing in the role.

Triple Threat

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Showtime’s Holiday Heart is a depressing story of a drag queen with a heart of gold who rescues a young girl and her junkie mom. Ving Rhames, a usually macho leading man, plays the main character, Holiday. While he’s usually known for his acting skills, critics were torn about Rhames’ performance. Some felt that it came across as forced and ingenuinewhile others were completely won over. Fans, on the other hand, fell in love with Holiday. Rhames’ inspiration for wanting to play a drag queen? “I’d never thought about what it would be like to be a triple minority,”