Happy Pride?

Sean Penn Slams “Timid and Artless” Idea That Straight Actors Shouldn’t Play Gay

Penn, who won his second Oscar for playing gay politician Harvey Milk, told The New York Times that his casting in the role “could not happen in a time like this”: “It’s a time of tremendous overreach.”
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For Sean Penn, all is fair in love—on camera, at least. The famously political actor spoke about life onscreen and off in a long interview with Maureen Dowd for The New York Times, discussing rumors about his marriage to Madonna as well as his Oscar-winning role as gay San Francisco politician Harvey Milk in 2008’s Milk. Penn said in the interview that his casting couldn’t happen today due to the current climate’s “timid and artless policy toward the human imagination.”

“I went 15 years miserable on sets. Milk was the last time I had a good time,” he told Dowd. Since Milk, Penn has starred in a number of film and television projects, including Terrence Malick’s The Tree of Life; The Professor and the Madman, opposite Mel Gibson; Paul Thomas Anderson’s Licorice Pizza; and Starz’s Watergate-inspired series, Gaslit, opposite Julia Roberts. Next up, he stars alongside Dakota Johnson in the two-hander Daddio, written and directed by newcomer Christy Hall.

Penn won his second lead-actor Oscar for playing Harvey Milk, the first openly gay man elected as a public official in California, in the eponymous 2008 film directed by Gus Van Sant. Milk, a gay icon, served as a member of San Francisco’s board of supervisors for nearly 11 months before he was murdered, along with San Francisco mayor George Moscone, by former political rival Dan White.

When asked whether it would be possible for Penn, a heterosexual-identifying actor, to play the homosexual Milk today, Penn immediately shot down the idea. “No,” he responded. “It could not happen in a time like this.” Penn went on to criticize the reasoning behind why a straight actor might no longer be the first choice to portray a queer character: “It’s a time of tremendous overreach,” he said.

Penn’s ire goes beyond modern attitudes. A prolific humanitarian aid worker who gave one of his Oscars to Ukrainian president Volodymyr Zelenskyy so that it could “be melted down to bullets they can shoot at the Russians,” Penn had a few choice words to say about convicted felon and presumptive Republican presidential nominee Donald Trump. For the record, he is also not a fan of reality television. “On one of my marriages, the background noise of life was a Housewives of Beverly Hills or another thing called Love Island,” he told Dowd. “Not even being in the room—I’m not saying this to be cute—I was dying. I felt my heart, my brain shrinking. It was an assault.” Penn was married to Madonna from 1985 to 1989; Robin Wright from 1996 to 2010; and Leila George, who is 30-plus years younger than Penn and is the daughter of actor Vincent D’Onofrio, from 2020 to 2022.

Suffice to say, Real Housewives and Love Island were not the soundtrack to Penn’s marriage to Madonna in the late ’80s. In the interview, he denied a persistent rumor that he once tied up the pop star and assaulted her with a baseball bat, then referenced a 2015 lawsuit in which he accused director Lee Daniels of defamation after Daniels implied that Penn had been physically abusive. Madonna provided an affidavit in which she declared that Penn did not assault her, and Penn ultimately settled with Daniels and withdrew the suit.

Penn told Dowd that he and Madonna are now on good terms, and that he’s not in a serious relationship at the moment. “I’m just free,” he said. “If I’m going to be in a relationship, I’m still going to be free, or I’m not going to be in it, and I’m not going to be hurting. I don’t sense I’ll have my heart broken by romance again.” Unless, of course, he falls for someone else who loves Bravo.