Will Eddie Redmayne become the latest actor to earn an Oscar for playing a character of the opposite gender?

By Drew Mackie
Updated February 25, 2016 01:55 PM
Credit: TIMOTHY A. CLARY/AFP/Getty Images

On Sunday, movie fans will find out if Eddie Redmayne wins Best Actor for his performance as trans woman Lili Elbe in The Danish Girl. Should Redmayne be victorious, he’d not only score back-to-back Oscars but he would also become the latest in a long line of actors who have courted Oscar attention by playing the opposite sex, playing a trans person or in some other way playing a character whose gender differs than the one of which the actors themselves identify.

Not that it comes without some criticism, of course. Also up for an Oscar this year is the second-ever openly trans person to be nominated in the 88 years of the awards: Antony Hegarty. Perhaps best known for the indie rock group Antony and the Johnsons, Hegarty has been recording as a solo artist for years – she’s got one of the better covers of Fleetwood Mac’s “Landslide,” BTW – and was nominated for Best Original Song for “Manta Ray,” recorded for the documentary Racing Extinction.

The only other known trans person to be nominated for an Oscar is the composer Angela Morley, who was nominated in 1975 for her work on the score for The Little Prince and again in 1978 for the Cinderella adaptation The Slipper and the Rose. Fans of the indie film Tangerine were hoping that it might get some love from the Academy this year or that its stars, Kitana Kiki Rodriguez and Mya Taylor, might get nominated as the first trans actors playing trans characters onscreen. It didn’t happen.

Nonetheless, there’s something to be said for actors who have found praise and success for playing cross-gender in a major way. Here’s who took home Oscar gold in doing so.

(Heads up: Some of these clips contain NSFW language.)

Jared Leto for Dallas Buyers Club (2014)

Leto truly transformed himself to play Rayon, a fictional trans woman character in the inspired-by-real-events story of Ron Woodruff smuggling drugs to AIDS patients. Winning Best Supporting Actor showed how far the onetime teen idol from My So-Called Life had come in his career. The award didn’t come without some criticism, however; a TIME op-ed, for example, noted that the role wasn’t as progressive as Hollywood would like to think since Leto’s character was played more for comic effect up until she died.

Jared Leto: My Arrests Led Me to Acting

Hilary Swank for Boys Don’t Cry (1999)

Considering that most audiences would have known her as the girl from The Next Karate Kid beforehand, Swank’s career-making performance as trans man Brandon Teena took Hollywood by surprise. But Swank didn’t just win the Best Actress Oscar for playing a person born biologically as a woman but living as a man. No, she got it for a portrayal of a sympathetic, tragic character murdered as a result of expressing his gender identity. It’s harrowing to watch.

Gwyneth Paltrow for Shakespeare in Love (1998)

To be clear, we get that Paltrow’s character is a woman who’s only dressing up as a man as a means to an end – performing onstage as an actor during a time when women were forbidden to do so. But it makes sense that Paltrow won for a part that had her spending a significant amount of screen time dressed as a man, especially when she did so at the height of her ‘It’ girl phase, when other actresses might have shied away from such a role.

William Hurt for Kiss of the Spider Woman (1985)

By today’s standards, Hurt’s prisoner character might be considered trans. That’s up for debate, but we’d be remiss if we didn’t note Hurt’s Best Actor win for the role. The recognition kicked off an impressive streak that saw him nab three more consecutive Oscar noms.

Linda Hunt for The Year of Living Dangerously (1982)

This will always be a bit of Oscars trivia that not enough people remember: Linda Hunt, the actress from NCIS: Los Angeles, took home the Best Supporting Actress award in 1984 for her role as Billy Kwan, a Chinese man. This made Hunt the first person ever to win an Oscar for playing a character of the opposite sex. After the fact, there has been some criticism of this role being played by Hunt, in the same way that people found it strange that John Wayne once played Genghis Khan or Emma Stone played a character of Chinese descent in Aloha. Still, it’s a remarkable performance to watch.

Other actors have been nominated for roles that crossed gender boundaries. Here are some of the most notable.

Glenn Close and Janet McTeer in Albert Nobbs (2011)

It seems a shame that Close has been nominated six times for an Oscar and has yet to win. If any of her roles should have snagged her Best Actress, it should have been Albert Nobbs, in which she does stellar work as a man who has for years been hiding the fact that he is biologically female. Close’s costar Janet McTeer was nominated in the same film for playing a biological female passing off as male.

Cate Blanchett in I’m Not There (2007)

Blanchett is the only female actor of a group of six to portray aspects of Bob Dylan’s public persona. The film was directed by Todd Haynes, who also directed Carol, for which Blanchett is nominated this year in the category of Best Actress.

Felicity Huffman in Transamerica (2005)

It’s one of the more touching road trip stories ever committed to film: Huffman plays Bree, a trans woman getting to know her long-lost son.

Jaye Davidson in The Crying Game (1992)

Pop culture at the time treated the secret of Davidson’s character, Dil, as a big, shocking thing, but it’s interesting re-watching the film today. Dil’s biological gender ultimately doesn’t change the feelings that Fergus (Stephen Rea) has for her. In a similar sense, Davidson wasn’t nominated for Best Supporting Actor for that one scene: Amid the headline-grabbing plot twist, critics praised Davidson for playing Dil as a complex woman with layered motivations

Julie Andrews in Victor Victoria (1982)

As with Paltrow in Shakespeare in Love, you’d have to have serious attention problems to not know that Andrews isn’t playing a drag queen; she’s playing a woman masquerading as a man who impersonates women onstage. Still, there’s some serious layering of gender going on here, and the fact that that Andrews did it so well earned her a third Best Actress nomination.

Dustin Hoffman in Tootsie (1982)

Isn’t it interesting that Tootsie would be released the same year as Victor Victoria? In a similar fashion, Hoffman’s performance in drag is mostly played for laughs, but the reason that Hoffman was nominated for Best Actor for the role is that he played his character in a way that suggests real depth – even when he’s dolled up as Dorothy.

John Lithgow in The World According to Garp (1982)

The third actor nominated for a cross-gender role in 1982, John Lithgow played Roberta, a trans woman who used to play professional football. Lithgow was nominated for Best Supporting Actor. In a 2014 interview with Huff Post Live, he explained his approach to the character: “[I] just decided to underplay everything [and] make her a perfectly normal person – in fact, a person who is utterly unaffected.”

Chris Sarandon in Dog Day Afternoon (1975)

Sarandon was nominated for Best Supporting Actor for his turn as Leon, the would-be wife of Al Pacino’s bank-robber character. In fact, Sarandon’s character’s gender is actually at the very heart of the plot, we find partway through: Pacino’s character is only trying to get money to fund Leon’s sexual reassignment surgery.