Sean Penn Says He ‘Went 15 Years Miserable on Sets’ After ‘Milk’ and Could Not Play Gay Role Today Due to a ‘Timid and Artless Policy Toward the Human Imagination’

Sean Penn recently said in an interview with The New York Times that 2008’s “Milk” was “the last time I had a good time” on a film set, adding: “I went 15 years miserable on sets.” While Penn earned critical acclaim and his second Oscar for best actor thanks to his portrayal of the openly gay politician Harvey Milk, he told The Times he could not star in the film today as straight actors playing queer characters has become too hotly debated in Hollywood.

“No. It could not happen in a time like this,” Penn said about not playing Harvey Milk in 2024. “It’s a time of tremendous overreach. It’s a timid and artless policy toward the human imagination.”

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As for his 15 miserable years on film sets, Penn said it was because he felt like “an actor who is playing a leading role and is a known actor and is being paid well [and] has a leadership position on a film and you’ve got to show up with energy and be a bodyguard for the director in some way.”

“I was faking my way through that stuff and that was exhausting,” he explained. “Mostly what I thought was just, ‘What time is it? When are we going to get off?’…I was sure it was done, but I didn’t know how I was going to keep my house running or travel freely or things like that if I stopped.”

Penn kept acting despite not entirely loving being on sets anymore — until his friend and fellow actor Dakota Johnson sent him the screenplay for their new film together, “Daddio.” The movie stars only the two actors and centers on a young woman who gets into a cab for the airport and has a life-changing discussion with the driver, a street philosopher from New York City’s Hell’s Kitchen.

“I felt like this could be a pleasant experience and that’s gonna matter to me now, maybe more than in the past,” Penn said about the film, a prediction that turned out to be true.

Head over to The New York Times’ website to read Penn’s latest interview in its entirety.

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