Sean Penn Is Convinced He Could Not Play Harvey Milk “In a Time Like This”

And yet straight people are still playing gay characters all the time.
A diptych of Sean Penn in ‘Milk and presentday Sean Penn.
Focus Features; Sonia Recchia/Getty Images

Another day, another addition to the seemingly endless discourse about whether it’s okay for presumably straight actors to take on gay roles. It’s a nuanced question, particularly when so many straight actors have received awards for playing queer characters over the years, including Sean Penn, who took home an Oscar in 2009 for playing the titular role in Gus Van Sant’s Milk.

Yet despite the fact that straight people still play gay all the time, Penn is somehow convinced that he wouldn’t be able to take a role like Harvey Milk today.

In her recent New York Times profile of Penn, columnist Maureen Dowd wondered aloud whether Penn could play the gay politician in 2024 given the ongoing, increasingly public conversations surrounding straight actors taking on gay roles.

“No,” he replied definitively. “It could not happen in a time like this. It’s a time of tremendous overreach. It’s a timid and artless policy toward the human imagination.”

Penn isn’t the only high-profile straight actor who has questioned their ability to play gay in recent years. In 2023, Cate Blanchett made headlines for wondering whether she’d be given “public permission” to play the titular lead of 2015’s Carol now, even though she had just received an Oscar nomination for playing another fictional lesbian in Tár.

Well, I have good news for both of them! Based on Hollywood’s recent output, the human imagination’s ability to picture ostensibly straight people in gay roles is still going strong. This year alone, Madame Web herself, Dakota Johnson, played a lesbian in the Max film Am I Okay?, and newly minted internet boyfriends Mike Faist and Josh O’Connor served us a churro-filled homoerotic situationship to remember in Challengers.

And don’t worry! Your straight fave’s gay Oscar isn’t going anywhere, either. Over the course of 95 years, according to our tally, over 80 Oscar nominations have gone to presumably cisgender, straight actors cast in queer and trans roles, from Hilary Swank for Boys Don’t Cry to Bradley Cooper for Maestro. Of those nominees, at least 15 went on to win an Academy Award.

In contrast, only five openly queer actors have received Oscar nominations for playing queer roles, and two of them — Jodie Foster’s nod for Nyad and Colman Domingo’s nomination for Rustin — only happened earlier this year. None of those nominees ended up winning. In fact, a queer actor has only won an Oscar for playing a queer character once when Angelina Jolie took home the 2000 Best Supporting Actress trophy for her role in Girl, Interrupted.

Of course, a trans character being played by a cis character is another matter, given that — as Jen Richards pointed out in the documentary Disclosure — it can quite literally contribute to ongoing violence against trans people, particularly trans women. But given how sharply anti-gay and anti-trans legislation has risen in the United States over the past few years, worrying about facing backlash from people who want to see authentic representation should perhaps be the least of celebrities’ worries.

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