When Sean Penn decided to cast his kids, Dylan and Hopper, in his 2021 movie Flag Day, he had no idea what he was really signing up for.
The 64-year-old actor and director was excited to have them involved in the project, but as the production progressed, a familiar sense of parental anxiety crept in. Penn, who shares Dylan, 34, and Hopper, 31, with ex-wife Robin Wright, admitted that he feared the casting could lead to “humiliation” for his children if they didn’t perform well.
Penn opened up to Us Weekly, explaining the emotional rollercoaster of being a parent who also calls the shots in the workplace: “The greatest joy is often relief. When you take a chance and invest in something, it could lead to disaster, but then when it doesn’t, it’s incredibly exciting.” The actor confessed that, in the rush of excitement to work with his kids, he didn’t consider the risk of them potentially failing, leaving him with an intense sense of relief when they both delivered “great” performances.
Despite this initial worry, Penn also revealed that part of the reason he wanted his kids to be involved was rooted in his personal preference. “I sleep best when my kids stay too late at a barbecue and pass out here,” he said. It wasn’t just about work, it was about keeping his family close, having them around where he could look out for them. The emotional connection to his children runs deep, especially when they’re close by during long nights of work.
Hopper, who starred alongside his father in Flag Day, recalled their relationship growing up and the strict discipline Penn had as a father. While they clashed frequently in the past, Hopper, now 31, appreciates his dad more than ever. “He was strict, and I was always getting into trouble,” Hopper admitted. “We butted heads for a long time. But it’s very lax now. He’s chilled out in his older age”! The bond between father and son has evolved, with Hopper now finding deeper respect for Sean’s work, particularly in films like Milk and The Falcon and the Snowman.
However, despite their close relationship, Hopper still struggles with his dad’s “novel-length” text messages. “I rarely read them!” he laughed, referring to the long texts his dad sends in increments. But beyond the text messages, Hopper has come to see his dad in a new light, particularly after Sean’s efforts in Haiti following the 2010 earthquake. “I’d never seen that side of him. It was just immediate, and he was really smart with it,” Hopper shared. Sean’s ability to stay calm in the midst of chaos is something his son admires deeply.
Ultimately, despite the early fears of humiliation, Penn’s decision to cast his children turned into a source of pride. His kids proved they could stand on their own, easing their father’s anxieties and proving that, sometimes, the best moments in life come when you’re relieved by a job well done.
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