A Short History of the Oscars and Cross-Gender Performances

There’s something to be said for actors who have found praise and success for playing cross-gender characters. Here's who were either nominated or took home Oscar gold in doing so.

Jared Leto as Rayon. Photo: Dallas Buyer's Club

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.

Gwyneth Paltrow. Photo: Shakespeare in Love

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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 she did a mighty fine job.

Hilary Swank. Photo: Boys Don't Cry

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.

Cate Blanchett. Photo: I'm Not There

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.

Felicity Huffman. Photo: Transamerica

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.

Drew Mackie writes for People.