Sean Penn and Robin Wright had a romance that seemed to be the stuff of Hollywood magic, and throughout their 13 years together, they welcomed two kids. The famous couple first struck up an on-set romance in 1989 while shooting the thriller State of Grace, and by 1991, Wright delivered their first child, daughter Dylan Penn, famously passing up the role of Maid Marian in the film Robin Hooddue to her pregnancy. Two years later, in 1993, they completed their family with the birth of their son, Hopper Penn.
These days, things look a little different. The celebrity pair parted ways in 2010 and have each remarried since the acrimonious split. Penn has said that he and Wright have different styles of parenting—and very “separate relationships” with their kids, he told comedian Marc Maron on his WTF Podcast. But if there’s one thing the two can agree on, it’s mutual love for their children, and support of their pursuits.
So, what are Dylan and Hopper up to now? At 29 and 27, the Penn kids are all grown up—and while they may be the spitting image of their parents, they're taking on Hollywood on their own terms. Read on to see what the kids of Sean Penn and Robin Wright look like today, and for an update on another celebrity's children now, See What Julia Roberts' 3 Kids Look Like as Teenagers.
Dylan has dabbled in modeling and acting, but wants to work behind the camera.
Getty ImagesThe star couple raised their children outside of the limelight in a small town just north of San Francisco, but that didn’t stop first born Dylan from eventually stepping into the spotlight. In 2013, she landed her first modeling campaign for Gap, Inc., and has since appeared on the pages of GQ, W, and Elle. She starred in a music video for the Nick Jonas song "Chains," and made her big screen debut in the Kevin Spacey film Elvis & Nixon. She'll next star in the movie Aramingo Avenue with Rosanna Arquette and her brother.
In an interview with Elle in 2014, she shared that while she has enjoyed her foray into modeling and acting, she considers it a launchpad—not the destination. “Modeling is not a passion of mine. I have been having fun with it, but it’s just to pay the bills. Writing, directing…anything behind the camera is what I want to do,” she shared.
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Hopper has followed a similar path.
Getty ImagesHopper has also followed in his parents’ footsteps. Yet despite the fact that he’s acted alongside Brad Pitt in 2017's War Machine and starred in the 2020 film Puppy Love opposite Paz de la Huerta, he still rejects the "actor" title. “I wouldn’t call myself an actor, really. Or a model,” he told the Evening Standard, noting that as recently as 2017 he still held a day job in a pizza restaurant.
Hopper has also acknowledged a history of addiction, which culminated in a drug-related arrest in 2018. According to People, Hopper agreed to get help after receiving some tough love from his famous father. “I went to rehab because I woke up in a hospital and my dad was like, ‘Rehab? Or bus bench?’ I was like, ‘I’ll take the bed,’” he said.
And to find out what more celebrity siblings look like now, check out See What Michael Jackson's Three Kids Look Like All Grown Up.
Dylan and Hopper have modeled together.
Hopper Penn / InstagramBeyond their independent Hollywood ventures and their upcoming movie together, the now-famous siblings have also modeled together. The pair posed side by side in an ad campaign for Fay’s Spring/Summer 2016 collection, looking every bit their parents’ children. Shot in the deserts of Palm Springs, the chic images were enough to help Hopper land a modeling contract with the top modeling agency Wilhelmina.
“They’re amazing people," dad Sean said about his children in 2018. "They’re both acting and modeling, an industry that I’m not very interested in but they seem to have fun with it.”
And for more celebrity kids following in their parents' footsteps, check out Heidi Klum's Adorable Selfie With Lookalike Daughter Leni.
They’re a close brother-sister pair.
Dylan Penn / InstagramYes, Dylan and Hopper Penn have led undoubtedly charmed lives as the children of A-list parents. Yet the sibling pair seem to have kept themselves somewhat grounded—perhaps the result of their childhood outside the limelight. Their Instagram accounts (check them out for yourself here and here) reveal surprisingly relatable lives full of friends, family, dogs, and sweet shoutouts in support of one another.
And for another celebrity offspring who's all grown up, check out See Celine Dion's Son All Grown Up at 20.
