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The Oscar-Winning Movie Sean Penn Doesn't Think He'd Get Away With Today

During an interview with The New York Times, Oscar-winning actor Sean Penn said that he doesn't think one of his most famous and acclaimed roles would be possible today. So does he have a point, or is he totally off base? (It's the second one, but we'll circle back to that.)

Speaking to Maureen Dowd, Penn said that, throughout a lot of his career, he's actively hated his work, which led him to explore activism and other projects and put acting and filmmaking aside. "I went 15 years miserable on sets," Penn told Dowd. "'Milk' was the last time I had a good time." This led Dowd to muse, in the article, that Penn's role in "Milk" was a game-changer for many reasons, but that it might be considered crossing a line today. "At the time, he got credit for being a straight man playing a gay one; but now there is sometimes an outcry when straight actors get cast as gay characters," Dowd wrote. "I wondered if he could even play [Harvey] Milk now."

"No," Penn replied after Dowd apparently voiced this query. "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 won an Academy Award for playing this real, influential figure — so who was Harvey Milk?

Who did Sean Penn play in Milk?

Just as a quick refresher, Harvey Milk is an important figure in LGBTQ+ history — and, yes, he was played by an actor who identifies as straight. In 2008, Sean Penn took on the role of Harvey Milk in a biopic simply titled "Milk," which tells the story of Milk's political rise and subsequent assassination. In the 1970s, Penn introduces us to Milk, a man grappling with his sexual identity who meets his lover Scott Smith (James Franco) in New York before the two move to San Francisco together, hoping to find a more inclusive and welcoming space out west. 

Ultimately, Milk becomes an activist fighting for gay rights and runs for office, but pays a personal price; Scott leaves, and Milk embarks upon a troubled and ultimately doomed relationship with a young man named Jack Lira (Diego Luna). From there, the film faithfully follows Milk's political ascendancy as he becomes the first openly gay public official in the state of California thanks to his seat on the San Francisco Board of Supervisors. As with Milk's real story, the film ends in tragedy when Milk, in the aftermath of defeating an openly homophobic effort called Proposition 6 (which intended to ban queer people from working in public schools), is gunned down by his erstwhile friend Dan White (Josh Brolin).

Penn does a phenomenal job in the film — again, he did win an Academy Award for his work — but it's pretty easy to poke holes in his argument that he couldn't play Milk again today — because certainly could. Here's why.

The world isn't quite as ideologically strict as stars like Sean Penn make it out to be

The argument that "you can't do things anymore, because of society" has been pretty common amongst people in Hollywood lately, most of whom are men (Jerry Seinfeld recently bemoaned the fact that you can't tell jokes anymore, for example; his former "Seinfeld" co-star Julia-Louis Dreyfus shot that down pretty quickly). As far as Sean Penn's argument goes, it ... simply doesn't make sense. Straight actors play queer characters all the time, and while arguments can and should be made that queer performers should play queer characters, there really isn't a whole lot of outcry when it doesn't happen. 

"Milk" came out in 2008, so here are just a few examples of actors who identify as straight playing queer characters that came after Sean Penn's movie. Cate Blanchett, arguably one of Penn's peers when it comes to prestige, played queer women in "Carol" in 2015 and "Tár" in 2022. Colin Firth was nominated for an Oscar for his role as a gay man in 2009's "A Single Man" and also played a queer characters in "Supernova" in 2020. Ewan McGregor took a cue from Firth and played a gay man in "I Love You, Phillip Morris," also in 2009, and played a real queer figure, like Penn, in Ryan Murphy's 2021 miniseries "Halston." Sterling K. Brown was nominated for an Oscar for playing a gay man in "American Fiction" last year, and this May, "Challengers" cast straight actors Mike Faist and Josh O'Connor as two tennis players with decidedly fluid sexualities.

This is by no means an exhaustive list, but the point stands: despite Penn's protestations, he could absolutely play Harvey Milk today. His new movie, "Daddio," is in theaters now.