There’s a joke that usually crops up around Twitter each Oscar season that the Academy Awards are like the Superbowl for the gays. Yet as much as the Academy can count on gay men to be a loyal segment of their fanbase, it certainly has done little to represent them in the awarded films. There are a few (literally, a few) exceptions, proving that every now and then they pay attention to a queer character or two. 

And though multiple gay men have won actual Oscars throughout the wide spread of categories, there are only a blessed few performances depicting gay characters that have gone on to take home the gold. Below are all of the roles that managed to do it, in the categories of both Best Actor and Best Supporting Actor.

Joel Grey: Cabaret 

So yes, the first Oscar to go to the performance of a gay character was never actually confirmed as a gay man. But this is Cabaret we’re talking about, and it doesn’t get much gayer than the Emcee of the Kit Kat Club in gay old Weimar Germany. Grey originated the role in the inaugural Broadway production, and his transition to the role on screen lost none of its magic. He steals every single musical number he’s in, from the impeccable duet of “Money” to the surreal opener “Wilkommen”. And given that this film came out in 1972, it’s pretty astonishing that conservative Academy voters felt comfortable awarding a gender-bending, confrontationally queer role like this.

William Hurt: Kiss of the Spider Woman

Released in the midst of the AIDS crisis of the mid 1980s, Kiss of the Spider Woman was a truly daring film, made even more daring by the fact that it managed to appeal to Academy voters. Is it problematic that the performance in question is a Latino character played by a white man? Sure, but William Hurt is devastatingly heartbreaking as Luis Molina, a fierce queen in prison for his homosexuality. He is enlisted to seduce his political prisoner cellmate, but in classic film noir fashion, mistakenly falls in love. It’s a fever dream of a movie, but Hurt’s performance as a gay man at odds with his life and sexuality is breathtaking.

Tom Hanks: Philadelphia

Tom Hanks would go on to win another Oscar a year later for that little movie called Forrest Gump, but he first struck gold here in his nuanced take on Andrew Beckett, a lawyer unfairly fired because of his positive diagnosis. At heart, it’s a courtroom drama, but Philadelphia is considered the first major Hollywood film to address the AIDS crisis and issues of homophobia and gay discrimination that were plaguing American society. And Hanks is able to ground his performance in reality, turning what would otherwise be a soap-opera tearjerker into a moving portrait of a gay man fighting for equality with his literal dying breaths.

Philip Seymour Hoffman: Capote

Truman Capote is one of the most unabashedly flamboyant gays in modern times; his voice alone has become infamous for its dramatic affectation. So bringing his larger-than-life persona proved quite a task for whomever took on the role in the 2005 biopic Capote. Luckily, Philip Seymour Hoffman delivered, recreating the author’s likeness to an almost eerie degree. The film mostly concerns the process of Capote writing his classic novel In Cold Blood more than the personal degrees of his sex life, but the film manages to capture his remarkable personality, one that was clearly at odds with the times in which he lived.

Sean Penn: Milk 

The story of Harvey Milk is one of the most important, and ultimately one of the most tragic, pieces of gay history in America. It’s a sensational story in which the revolutionary climate of gay acceptance in 1970s San Francisco led to the election of Harvey Milk, California’s first openly gay elected official and one of the nation’s first, only to end in his assassination. But the film never gives into the tired old tropes of a typical biopic, thanks in large part to Sean Penn’s bravura performance of Milk, one that earned him his second Oscar. Penn captures his unfailing idealism, even as we watch it deteriorate his personal life and the men who love him. His honesty still makes the inevitable ending a shock, even though we know it’s coming.

Christopher Plummer: Beginners

Coming out of the closet takes a lot of courage for someone of any age, but can you imagine coming out of the closet at the age of 80? How would your remaining family react to such a late life change? The answer is poignantly revealed in Beginners, in which Ewan McGregor has to deal with his octogenarian father coming to terms with his long-buried sexuality. As the father, Christopher Plummer is endearingly cute; it doesn’t get more satisfying than watching a grandpa go to his first gay rave. Academy members seemed to think so too, making Plummer the oldest Oscar winner yet.

BONUS: Jared Leto: Dallas Buyers Club 

Though his performance was technically as a trans woman and not as a gay man, it would feel wrong not to include Jared Leto on this list. The decision to cast Leto instead of an actual trans actress created quite a bit of controversy, and it’s a debate that continues to rage at this year’s awards for Eddie Redmayne’s nominated performance in The Danish Girl. But poor casting decisions aside, Leto still delivered. As Rayon, a trans woman suffering from HIV, Leto went to breathtaking heights to bring this character to life, not the least of which included losing over 30 lbs and waxing his entire body. Rayon provided the comic backbone of the film, but as with any film about HIV, things don’t turn out too sunny. The Academy loves to award transformations, and few in recent memory were as pronounced as Leto’s.  

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