There’s a bitter irony to Hollywood’s relationship with the LGBT community: We’re everywhere in the film industry, but it’s only now that actors are even starting to have successful careers outside the closet.
And when it comes to LGBT representations on the big screen, studios almost always cast heterosexual cisgender performers—and then shower them in Oscar gold for it.
That’s not to devalue the work done by Tom Hanks in Philadelphia or Cate Blanchett and Rooney Mara in Carol. But to this day no LGBT actor has ever won an Academy Award for playing an LGBT character.
Below, we take a look at 11 times that the Academy rewarded straight actors for taking queer parts.
William Hurt, “Kiss of the Spider-Woman” (1985)
Hurt was the first actor to win an Oscar for playing gay—scoring a Best Actor trophy as flamboyant drag queen Molina in Kiss of the Spider Woman.
While the film is excellent, Molina’s fate—shot, killed and tossed into a dumpster—still played into the Hollywood trope that queers end up dead. In fact, half of the characters on this list met untimely (and usually gruesome) ends.
Tom Hanks, “Philadelphia” (1993)
In Philadelphia, Hanks played Andrew Beckett, an attorney who takes his firm to court after they fire him for having AIDS.
In the real world, HIV-positive people were still being discriminated against in the workplace—and LGBT still are—but Hanks took home the first of many Best Actor Oscars.
Hilary Swank, “Boys Don’t Cry” (1999)
Hilary Swank received her first Oscar for the harrowing bio-film Boys Don’t Cry. In real life, Brandon Teena was brutally murdered for being a trans man, but Swank took home Best Actress and was instantly thrust into A-list Hollywood.
Nicole Kidman, “The Hours” (2002)
Kidman portrayal of Virginia Woolf in The Hours earned her a Best Actress award, prosthetic nose be damned. Though married, Woolf had a sexual relationship with acclaimed writer Vita Sackville-West.
Charlize Theron, “Monster” (2003)
Theron turned to two tried-and-true methods to get Oscar gold—playing a tragic gay character and uglying herself up—as convicted serial killer Aileen Wuornos in Monster.
Philip Seymour Hoffman, “Capote” (2005)
Hoffman won the Best Actor award in Capote playing the Breakfast at Tiffany’s author during the peroid he was researching his true-crime masterpiece, In Cold Blood.
Penélope Cruz, “Vicky Cristina Barcelona” (2008)
Cruz’s character enters a polyamorous relationship with Scarlett Johansson and Javier Bardem. Not a terrible gig, really, and she scored a Best Supporting Actress Oscar for it.
Sean Penn, “Milk” (2008)
Penn earned the Best Actor award for his gripping portrayal of LGBT activist and politician Harvey Milk—and helped raise national awareness of this trailblazing hero.
Natalie Portman, “Black Swan” (2010)
In Black Swan Best Actress winner Portman played a panic-gripped ballerina who has sex with Mila Kunis. Well, maybe—it could have been a dream sequence. (We’re still not sure.)
Christopher Plummer, “Beginners” (2011)
Plummer has given many accomplished performances over his very long career. His role as an elderly man who comes out after the death of his wife, however, was the role that brought him home the gold.
It was a beautiful performance—and reminded us that love, gay or straight, is not just for the young.
Jared Leto, “Dallas Buyers Club” (2013)
Jon Adams contributed to this feature