Sean Penn Says Oscar-Winning Milk Was His Last 'Good Time' Making a Movie: 'I Went 15 Years Miserable on Sets'

Sean Penn has fond memories of making his Oscar-winning movie Milk.

Speaking to The New York Times in an interview published June 22, the actor, 63, reflected on making the 2008 film, in which he starred as real-life activist Harvey Milk — a San Francisco supervisor and California’s first openly gay elected official. Milk was murdered in 1978 by his onetime colleague, former supervisor Dan White, who also killed San Francisco mayor George Moscone.

Admitting that the movie — which earned him his second Best Actor Oscar after his 2003 win for Mystic River — was “the last time I had a good time” on a film set, the Daddio star added to the outlet, “I went 15 years miserable on sets.”

“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 continued. “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?’ ”

“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,” he added. 

Penn went on to explain that his experience on film sets changed after his friend — and neighbor — Dakota Johnson sent him the script for their new film Daddio. 

The movie, which screened at the 2024 Tribeca Film Festival earlier this month, stars Johnson as a passenger in a taxicab driven by Penn's character and follows the pair as they engage in a life-changing discussion after Johnson's character arrives at N.Y.C.'s JFK Airport and takes a ride into Manhattan.

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“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 of the film.

Johnson, 34, added to the outlet of Penn, “He’s quite known for being tough and intimidating, but there’s a sweet boy in there. There’s a real tenderness in him.”