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Sean Penn Reveals 2008 Movie About Harvey Milk ‘Was the Last Time’ He Enjoyed Being on a Film Set

Photo Credit: Visculmania / Focus Features / MovieStillsDB
Photo Credit: Visculmania / Focus Features / MovieStillsDB

Sean Penn is one of the most recognized actors in Hollywood, appearing in a slew of movie and television productions. Over his decades in the entertainment industry, he’s spent a lot of time on film sets, something that, over the past decade, hasn’t been an enjoyable experience for the actor.

Sean Penn as Harvey Milk in 'Milk'
Milk, 2008. (Photo Credit: Visculmania / Focus Features / MovieStillsDB)

In a 2024 interview with The New York Times, Penn revealed that it’s been over 15 years since he found enjoyment on a film set, specifically citing 2008’s Milk. In the film, he portrayed politician and LGBTQ+ rights activist Harvey Milk.

Milk was the first openly-gay man to be elected to public office in California, securing a position on the San Francisco Board of Supervisors in 1977. During his short time in office, he fought for the rights of the LGBTQ+ community, introducing a bill that banned discrimination based on sexual orientation when it came to employment and accommodation.

On November 27, 1978, during his first year on the Board of Supervisors, Milk was assassinated by disgruntled former city supervisor Dan White, who was sentenced to seven years in prison for the murder. He only served five.

Milk was widely praised upon its release, with the film receiving a multitude of nominations and wins during awards season. The most notable were the Oscars for Best Actor and Best Original Screenplay.

Sean Penn as Harvey Milk in 'Milk'
Milk, 2008. (Photo Credit: Visculmania / Focus Features / MovieStillsDB)

In his interview with The New York Times, Penn said that the filming of Milk “was the last time I had a good time” on set, with him describing the last decade or so as “miserable.”

He added, “I feel like an actor who is playing a lead 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 good body guard in some way. I was faking my way through the 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,” he continued. “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 reportedly felt this way up until fellow actor Dakota Johnson presented him with the script for Daddio (2023). “I felt like this could be a pleasant experience and that’s gonna matter to me now, maybe more than in the past,” he shared.

Sean Penn sitting in a chair
Sean Penn appearing on Jimmy Kimmel Live! with June Squibb and The Avett Brothers, 2024. (Photo Credit: Disney / Randy Holmes / Getty Images)

The actor also touched upon whether he, a heterosexual male, could portray Milk on-screen today “No,” he responded. “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.”

His comments come at a time when the topic has become a major point of discussion, both online and in Hollywood.

Many took to X (formerly Twitter) to share their thoughts, including @AlliCinema, who commented, “Did Sean Penn just say: now that we’ve made progress, we should regress?”

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Penn has not responded to the media attention his comments have garnered.

Clare Fitzgerald

Clare Fitzgerald is a Writer and Editor with eight years of experience in the online content sphere. Graduating with a Bachelor of Arts from King’s University College at Western University, her portfolio includes coverage of digital media, current affairs, history and true crime.

Among her accomplishments are being the Founder of the true crime blog, Stories of the Unsolved, which garners between 400,000 and 500,000 views annually, and a contributor for John Lordan’s Seriously Mysterious podcast. Prior to its hiatus, she also served as the Head of Content for UK YouTube publication, TenEighty Magazine.

In her spare time, Clare likes to play Pokemon GO and re-watch Heartland over and over (and over) again. She’ll also rave about her three Maltese dogs whenever she gets the chance.

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