Most actors of Sean Penn‘s level don’t move without a big paycheck and a long list of conditions. But Penn has done the opposite more than once, telling a director he’d work for a single dollar as long as they told him where to show up.
The actor shared this during a chat with his old friend Julia Roberts for Variety and CNN‘s “Actors on Actors” series. The conversation covered a lot of ground, including cancel culture, shame, and his recent films ‘One Battle After Another‘ and ‘After the Hunt.’
Sean Penn’s Iconic Offer to Work with Top Directors
When Roberts brought up chasing directors she admired, like Luca Guadagnino, Penn said he’d done the same thing himself, just to work with people he respected.
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“I’ve done that a couple of times over the years, where I’ve met a director that I admired a lot and said, ‘Give me a dollar and tell me where I’ve got to go.'” He named three names without hesitating, Terrence Malick, Alejandro González Iñárritu, and Paolo Sorrentino. Three very different directors, but all of them mattered enough to Penn that the money didn’t.
Malick tops the list for a reason. He directed Penn in ‘The Thin Red Line‘ back in 1998, then again years later in ‘The Tree of Life,’ the film that won the Palme d’Or and centered on a broken family in 1950s Texas. Working with Malick wasn’t always easy. Penn has admitted before that he almost walked off both films because he couldn’t always tell where the story was headed. It is because Malick barely uses a traditional script.
Still, Penn has called the ‘Tree of Life‘ script one of the best pieces of writing in English, and says he learned to trust Malick’s instincts even when he didn’t understand them.
Inside Sean Penn’s Bond With Alejandro González Iñárritu
Then there’s Iñárritu, who put Penn in the role of a dying mathematician in ‘21 Grams‘ back in 2003, a movie known for jumping around in time, also starring Naomi Watts and Benicio del Toro.
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The two stayed close after that. Close enough that when Penn handed Iñárritu his Best Director Oscar for ‘Birdman‘ in 2015 and made a joke about his green card that got a lot of attention, Iñárritu just laughed about it backstage. He said it was the same blunt humor they’d built between them while working together.
How Paolo Sorrentino Turned Sean Penn Into A Rock Star On Screen
Last is Sorrentino, the director behind ‘The Great Beauty‘ and ‘The Hand of God.’ He cast Penn as an aging, Robert Smith-looking former rock star tracking down a Nazi war criminal in ‘This Must Be the Place,’ from 2011. They met back in 2008 when Penn ran the jury at Cannes and Sorrentino’s film ‘Il Divo‘ was competing.
Less than a year later, Sorrentino had a script ready for him. Sorrentino has spoken warmly about working together since, once calling Penn’s transformation for the role “beautiful,” and adding that the better an actor is, the easier they usually are to direct.
Penn summed it up simply: “That was Terry Malick and Alejandro González Iñárritu. Oh, and Paolo Sorrentino. Three times.” It’s a small story, but it says a lot. After four decades of being picky about roles, Penn was never really chasing money. He was chasing the right director.
Sean Penn’s ‘One Battle After Another’ Role
This story comes at a good time for Penn. His role as the frightening Col. Steven J. Lockjaw in Paul Thomas Anderson’s ‘One Battle After Another‘ got him a Golden Globe nomination and was one of the standout parts of his awards season in 2025, after years of Penn saying he felt distant from acting.
In that same conversation with Roberts, Penn said discomfort belongs in art, and that audiences today look away from hard subjects too quickly. It’s a mindset that fits right in with a guy who was once willing to hand over a single dollar bill and go wherever the work took him.
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