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Home Entertainment

Sean Penn Gets Emotional About the ‘Greatest Joy’ of Working With His Kids

by DigestWire member
May 8, 2025
in Entertainment
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Sean Penn Gets Emotional About the ‘Greatest Joy’ of Working With His Kids
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Sean Penn is all about taking chances — both on and off screen.

From his various Oscar wins to being a proud dad of two, Penn goes all in with whatever he does, and with the knowledge  that following his gut usually delivers the best results. In an exclusive interview with Us Weekly, the actor, 64, recalled one particular risk in which he chose to cast daughter Dylan and son Hopper, then in their 20s, in his 2021 thriller Flag Day. It’s a decision he’ll never regret as a filmmaker or a father — even when some parental anxiety inevitably kicked in.

“I don’t know if this is true of everyone, [but] the greatest joy [in life] is often relief. It’s when you take a chance with something, you invest in it. And sometimes with so much excitement, you forget the risk that you put yourself or someone else at,” Penn said while discussing his new film Words of War. “And when I’ve asked my son Hopper or daughter Dylan to do something like act in a movie, it’s only later you realize, ‘Jesus, this could have been a setup for their humiliation.’ And then to experience that relief when they’re great … It’s exciting to do.”

Penn admits that some of the motivation behind the decision to cast his children, whom he shares with ex-wife Robin Wright, is selfishness. “I sleep best [when] my kids stay too late at a barbecue that goes into the night and pass out here and I know everybody’s in proximity. I feel the same way with work when they’re around,” he told Us.

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But it’s that kind of heart-first thinking that has led him to his decades-long, decorated career as an actor, director and executive producer, and his latest risk-taking venture comes in the form of Words of War. The film is based on the life and career of journalist and human rights activist Anna Politkovskaya, who reported on political and social events inside early 2000s Russia until she was murdered. Penn joined the project as an exec producer after shooting had wrapped, happy to serve as a “champion” of a project he believed in.

“I was shown the film and I just said, ‘Anything that I can do that would be helpful [I’ll do],’” he explained. “It was great storytelling. I thought [it was] necessary and exciting, the idea that it exists and can be shared [as a] cautionary tale.”

SeanPennGettyImages-1491501485.jpg
Sean Penn Andreas Rentz/Getty Images

Penn also pointed to Maxine Peake’s performance as Anna as an additional tipping point for his involvement, as well as that of Jason Isaacs, who Penn believes has deserved his flowers for quite some time.

“The world has known [Jason], but between White Lotus and this, it’s about time this great actor has this kind of run,” he shared. When it comes to whether he turned in to watch his longtime pal’s recent stint on the hit HBO series, Penn confessed: “I was upset all week waiting for the next one.”

Beyond what’s on the screen, the project is  also about sparking real conversations about the world at large for Penn, who is clearly interested in telling stories that resonate for far longer than after the credits roll.

JasonIsaacsMaxinePeakeWordsofWar
Jason Isaacs, Maxine Peake in Words of War Mike Eley

“The situation we are in now, we feel words are weaponized now, very much so, and opinions and truths. I think we have lost our ability to discuss, to debate,” he explained. “You have to listen to people’s opinions that you don’t agree with.”

But we shouldn’t shy away from those heated discussions, Penn added. “We’ve got to thrash this out. We can’t hold down the shutters, as none of us will grow and move forward and learn,” he said.

Penn saw that passion in Anna’s extraordinary journalism, as did Peake herself through the lens of portraying her.

Zach Braff! Olivia Wilde! Ben Affleck! Hollywood Actors Turned Directors

“The words that she put on the paper were so effective and she could connect with an audience so brilliantly, and her writing was beautiful, even when she was describing some of the most horrific incidents,” Peake told Us at the film’s premiere earlier this month. “It made you want to sit up and pay attention when a lot of the time, as we do, we can turn away from those reports. [Thinking], ‘I don’t want to know. There’s nothing I can do’. And journalists like Anna engage you and make you realize there’s something all of us can do.”

Words of War is out in theaters and on digital now.

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