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Actor Clint Eastwood once directed Sean Penn in the critically acclaimed film Mystic River. But when they first collaborated, Penn was caught by surprise with how Eastwood worked behind the camera.

Sean Penn once called working with Clint Eastwood an ‘unusual case’

Sean Penn smirking while wearing a suit.
Sean Penn | Axelle/Bauer-Griffin/FilmMagic

Penn collaborated alongside Clint Eastwood on the 2003 feature Mystic River. The movie followed the murder of a young girl, and an ex-con’s attempt at trying to solve the crime. The film was nominated for several Oscar awards, and furthered Eastwood’s reputation as a director.

Although Penn enjoyed the process of working alongside the Dirty Harry star, some of Eastwood’s methods as a filmmaker was different than what Penn was used to.

“Clint [Eastwood] is a very unusual case. The only thing I learned from him was the value of a sense of calm and quiet on a set. How he makes a movie is a mystery to me,” Penn once said in an interview with Rolling Stone.

Penn asserted that Eastwood’s speed caught him off guard at the end of filming Mystic River.

“I remember checking into a hotel in Boston to start on the very first day of shooting. Nine weeks later from that day, the entire movie was finished — including the score that he wrote and recorded! This year, two major pictures, and acting in one of them? I don’t know how he does it,” Penn said.

Sean Penn thought Clint Eastwood might never speak to him again if he didn’t read the script for ‘Mystic River’

Although Penn was approached for the Eastwood-directed project, he was initially hesitant to even look at the script. The U-Turn co-star had just made a film that he believed might thematically overlap with Eastwood’s Mystic River. But he had a change of heart sometime later because of Eastwood’s insistence.

“Clint Eastwood handed me a script and said, ‘Read it and see what you think.’ I wasn’t interested because the theme was too similar to a movie I’d just made. But I really like Clint and we’ve had a lot of chuckles. A year later, he called again and I figured, ‘This guy will never talk to you again if you turn him down. I got about ten pages into the script when I called him and said, ‘This just hammers me,’” Penn said in an interview with Oprah.

How Sean Penn felt about winning the Oscar for ‘Mystic River’

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As many know, Penn won an Oscar for Best Actor in a leading role thanks to his portrayal in Mystic River. The Gaslit star was greatly appreciative of his victory, but it wasn’t a win he believed was a sure thing.

“It was a relief to have the night over with. I don’t care what anybody says, you’re surprised when you hear your name called. It’s like if you scratch one of those tickets, you never expect it to say you’ve won $25. So the surprise makes me nervous. I saw my mother’s face and Clint’s face, and that was going to bust me. I had to look past them,” Penn said.