Sean Penn attends the "Black Flies" photocall at the 76th annual Cannes film festival at Palais des Festivals on May 19, 2023 in Cannes, France Source: Pascal Le Segretain/Getty Images

Sean Penn Says He Couldn't Play Harvey Milk Today, Slams 'Timid' Hollywood Casting

Kilian Melloy READ TIME: 2 MIN.

"Milk" actor Sean Penn says that these days he wouldn't be able to play Harvey Milk, the role that garnered him his second Oscar, thanks to "timid" casting around who can play what roles.

"At the time, he got credit for being a straight man playing a gay one," The New York Times recalled of Penn's casting in the 2008 Gus Van Sant-directed biopic of America's first openly gay elected official, "but now there is sometimes an outcry when straight actors get cast as gay characters."

Penn spoke to the point. "It could not happen in a time like this," he told the Times, Variety relayed.

"It's a time of tremendous overreach," Penn went on to say. "It's a timid and artless policy toward the human imagination."

What's more, the acclaimed actor, director, and human rights advocate added, "'Milk' was the last time I had a good time" as an actor on a film shoot. After making that film, he said, "I went 15 years miserable on sets."

Penn offered a happy ending to that story, though, saying that his role in the new movie "Daddio" (written and directed by Christy Hall), a two-hander that also features Dakota Johnson, revived his love of starring in films. It was Johnson who brought the script to his attention.

"I felt like this could be a pleasant experience and that's gonna matter to me now, maybe more than in the past," Penn reflected.

The 63-year-old actor is already back to work, filming a movie with director Paul Thomas Anderson and co-star Leonardo DiCaprio, the Times noted.

Penn, who was famously married to Madonna (before wedding Robin Wright and, after Wright, Leia George), told the newspaper that he's single now, and he likes it that way. He described one marriage – he declined to specify which – that involved the TV being tuned to fare like "a 'Housewives of Beverly Hills' or another thing called 'Love Island'" – a state of affairs Penn likened to "an assault."

"Not even being in the room – I'm not saying this to be cute – I was dying," Penn said. "I felt my heart, my brain shrinking."

Now, the actor explained, "I'm just free."

Added Penn: "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."


by Kilian Melloy , EDGE Staff Reporter

Kilian Melloy serves as EDGE Media Network's Associate Arts Editor and Staff Contributor. His professional memberships include the National Lesbian & Gay Journalists Association, the Boston Online Film Critics Association, The Gay and Lesbian Entertainment Critics Association, and the Boston Theater Critics Association's Elliot Norton Awards Committee.

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