More from EW
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Jared Leto, Dallas Buyers Club (2013)
Even off screen Leto stayed in character as Rayon, the fictional transgender business partner of real-life AIDS activist Ron Woodroof (Matthew McConaughey). LGBT rights groups have criticized the filmmakers for inventing the character and for not casting a transgender actor. Accepting the Golden Globe on Jan. 12, 2014, Leto dedicated the prize ''to the Rayons of the world.''
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Glenn Close, Albert Nobbs (2011)
Close worried that audiences wouldn't accept her as Albert, a 19th-century Irishwoman posing as a man. But after early makeup tests, she told EW, ''I remember the moment I looked up and saw that it wasn't me anymore. It made me weep because I thought, 'This is possible.'''
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Janet McTeer, Albert Nobbs (2011)
McTeer wore a prosthetic nose and a wig to accentuate her transformation into a house painter who lives as a man and is happily married to a woman — and who inspires Glenn Close's Albert.
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Cate Blanchett, I'm Not There (2007)
Blanchett was one of six actors who played Bob Dylan in Todd Haynes' refracted biopic. But she was the only woman — and the only one to score an Oscar nod.
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Felicity Huffman, Transamerica (2005)
Huffman was best known for ABC's Desperate Housewives when she was cast as Bree, a pre-op male-to-female trans person. ''I was never a beauty,'' she told EW in 2005, ''so it was never something I had to safeguard.''
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Hilary Swank, Boys Don't Cry (1999)
To research her Oscar-winning (and career-making) turn as real-life transgender teen Brandon Teena (born Teena Brandon), Swank, then a relative unknown, lived as a man for 30 days in L.A. ''I was treated poorly by people in stores, people that I had known as Hilary,'' Swank told EW in 1999. ''I cried for two days straight.''
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Gwyneth Paltrow, Shakespeare in Love (1998)
Male-to-female cross-dressing was a staple of Shakespearean theater, but Viola (Paltrow, in an Oscar-winning role) bucked convention by disguising herself as a man to join the Globe's troupe.
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Jaye Davidson, The Crying Game (1992)
The acting novice, then 24, played Dil, the transgender singer at the center of Neil Jordan's noir drama. Davidson didn't cry over losing to Unforgiven's Gene Hackman. ''If they gave it to me, it would be very insulting for the other people, who are actors,'' he told EW in 1993.
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Linda Hunt, The Year of Living Dangerously (1983)
Hunt is the only person ever to win an Oscar for playing a member of the opposite sex. Hunt's character, photographer Billy Kwan, isn't transgender — he's simply a man.
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Dustin Hoffman, Tootsie (1982)
Hoffman earned his fifth Oscar nom for his role as an actor who pretends to be a woman to win a part on a soap opera. Mid-shoot, he even visited his daughter's school and introduced himself as her aunt Dorothy.
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Julie Andrews, Victor Victoria (1982)
In Blake Edwards' musical about a singer who finds work at a drag bar, Andrews played a woman playing a man playing a woman, a tricky double feat that earned the actress the third Oscar nomination of her career. (She'd won for 1965's Mary Poppins.)
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Robert Preston, Victor Victoria (1982)
Preston's sole Oscar nomination was for the role of Toddy, a drag performer who persuades Victoria (Julie Andrews) to pass herself off as a man. The part was reportedly intended for Peter Sellers, who had died in 1980.
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John Lithgow, The World According to Garp (1982)
Lithgow did no Method-y research for this touching, understated turn as a transgender former football player. He got an Oscar nod anyway.
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Chris Sarandon, Dog Day Afternoon (1975)
Sarandon's turn as the pre-op male-to-female lover of a bank robber (Al Pacino) was one of the first transgender roles in a studio film. At 14 minutes, it's also one of the shorter performances ever to earn an Oscar nomination.
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Jack Lemmon, Some Like It Hot (1959)
Lemmon (right) and Tony Curtis played musicians who join an all-girl band to hide from the Mob. Banned in Kansas, Billy Wilder's classic earned Lemmon his second nom, after winning for 1955's Mister Roberts.
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Judy Garland, A Star Is Born (1954)
In a minstrel-tinged performance, Garland sang ''Swanee'' wearing a man's hat and suit — an act that was considered radical in past eras, but by the mid-1950s was apparently acceptable for the veteran of American musicals. Garland, then 32, lost Best Actress to Grace Kelly for The Country Girl.
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Marlene Dietrich, Morocco (1930)
While the film's romance between a legionnaire (Gary Cooper) and a nightclub singer (Dietrich) has been largely forgotten, the sight of Dietrich performing in a top hat and tails — and kissing a female patron on the lips — remains one of the most iconic images in film history.