Sean Penn says he couldn’t star in ‘Milk’ today: ‘It could not happen in a time like this’

In a New York Times profile to promote his film “Daddio,” actor and activist Sean Penn griped about how things in Hollywood have changed since he starred in “Milk” in 2008. He said the industry has become “timid and artless,” and he’s been “miserable” on sets for the past 15 years.

In the interview, Penn told writer Maureen Dowd that he focused more on journalism and political activism after “Milk,” because he was having a bad time in the film industry. 

“I went 15 years miserable on sets,” he said. “‘Milk’ was the last time I had a good time.” 

Penn won his second Academy Award for Best Actor for his performance as Harvey Milk, who as a member of the San Francisco Board of Supervisors was the first openly gay elected official in California and was assassinated by a disgruntled political opponent in 1978. 

At the time, Penn was rewarded for being a straight man playing a gay character. But cultural mores have shifted since then, and Penn would likely face more criticism now from people who would argue that a gay actor should play Milk. Dowd asked Penn if he thought he could be cast as Harvey Milk in 2024. 

“No,” he said. “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.”

He said that in the years since he starred in Gus Van Sant’s film, he has not enjoyed his acting work. “I feel like an actor who is playing a leading role and is a known actor and is being paid well 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,” he said. “I was faking my way through that stuff and that was exhausting. Mostly what I thought was just, ‘What time is it? When are we going to get off?’” He added that he kept working in films he didn’t enjoy because he needed the money. 

During that time, he has worked with top-tier directors like Terrence Malick (“The Tree of Life”) and Paul Thomas Anderson (“Licorice Pizza”), but he’s also appeared in many movies and TV shows that didn’t make an impact. He also directed and starred in 2021’s “Flag Day,” with his daughter Dylan Penn. He says that he chose to star in “Daddio,” an indie drama in which he and Dakota Johnson are the only performers because it seemed like it could be a pleasant filming experience, which matters more to him now than it used to. 

Elsewhere in the interview, Penn talks about being single after a string of high-profile relationships (“I don’t sense I’ll have my heart broken by romance again”), the end of his tumultuous marriage to Madonna (“I had a freaking SWAT team come into my house”), and his new friendship with Hunter Biden (“a very, very insightful guy”).

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