Emily Mack
Sean Penn is one of the most respected actors of his generation… and he’s also a bit of a Lothario. Penn has engaged in high-profile relationships with many famous women. But he only has children with one: ex-wife and fellow A-lister Robin Wright. They share a son and a daughter: Dylan Penn and Hopper Penn.
Videos by Rare
Sean Penn and Robin Wright
Sean Penn was raised in a Hollywood family, by father Leo Penn, an actor and director, and Eileen Ryan, an actress. Following in their footsteps, Penn found early fame in 1982 with Fast Times at Ridgemont High, playing stoner Jeff Spicoli.
Shortly after, Penn was cast alongside Elizabeth McGovern and Nicolas Cage in Racing with the Moon. Penn and McGovern struck up a romance and were briefly engaged. However, Penn moved on quickly — first with Susan Sarandon and then Madonna at the height of her “Material Girl” era. She and Penn met on the set of that music video. They married in 1985, just one day before Penn’s 25th birthday. Madonna was 27.
But the marriage that followed was tumultuous. Reports of Penn’s violent outbursts characterized the wild young actor, as he was arrested for the assault of multiple journalists, as well as a songwriter (who supposedly made a pass at Madonna), and a film extra. There were rumors of domestic assault, too. Penn allegedly struck Madonna multiple times, and at one point she reportedly made — and withdrew — an assault complaint with the police. In 1989, they divorced. However, the pair remained friends and in 2015, Madonna said the rumors of Penn’s abuse are false.
After the divorce, Penn took up with actress Robin Wright at the height of her Princess Bride fame. They had two children together: a daughter named Dylan Frances, after Bob Dylan, born in 1991, and son named Hopper Jack, after Dennis Hopper, born in 1993.
Two years later, though, Penn and Wright separated and Penn began dating Jewel. He even followed her on tour. But the romance was short-lived and in 1986, Penn and Wright reconciled. They married in April of that year… but remained sort-of on-and-off. The couple filed for divorce twice, and got back together twice, before officially divorcing in 2010. By that point, Dylan was grown and Hopper was nearly 17. Their divorce settlement and custody agreement were handled privately.
Since then, Penn has dated Charlize Theron and the Australian actress Leila George, daughter of Vincent D’Onofrio. He and George married in 2020 but filed for divorce just a year later.
Wright, too, remarried after Penn, to Saint Laurent executive Clément Giraude, though she recently filed for divorce.
Dylan Penn
Dylan Penn and her brother were raised by their parents away from Hollywood, in the Northern California town of Ross. She attended the private Marin Academy for high school before heading off to the University of South California. But she dropped out after one semester. Since then Dylan has held a variety of odd jobs, including pizza delivery girl, waitress, hostess, freelance editor, and advertising intern. Basically, Dylan is a true gigging millennial.
She’s also made a name for herself modeling and has appeared on Gap billboards, as well as in GQ, Elle, and W. Dylan also acts, occasionally. She starred in the 2015 horror movie Condemned and in her father’s 2021 drama Flag Day. Brother Hopper Penn also co-starred.
Hopper Penn
Hopper Penn is in the news after landing in People’s Sexiest Man Alive edition! Penn was featured in a new section highlighting famous sons. His accompanying interview is also generating buzz, as Harper opened up about having Sean Penn as a father.
“He was strict, and I was always getting into trouble. We butted heads for a long time. But it’s very lax now. He’s chilled out in his older age!” Harper told People.
Based on his aggressive reputation, having Penn as a dad sounds tough. But it turns out, Hopper needed the discipline… because he was addicted to crystal meth. Hopper discussed the experience in 2017 with ES Magazine and reflected on his father’s own form of tough love.
Hopper Penn on Instagram
“I was doing a lot of stuff, but meth was the main one that brought me down,” Hopper, then 23, said at the time. “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.’ ”
Hopper also went into detail about his parents’ relationship, explaining the toll that their conflicts took on the kids:
“Honestly? I was pretty mad, because they had split up before and then got back together, and then they did it again. So it was like, ‘Pick which one you’re gonna do.’ …I was young and thinking: ‘Are you just f— with me and my sister?’ I mean it was not the best. It was kind of tough talking to them. Because they were both pretty broken too, I think.”
— Hopper Penn in ES Magazine via People
But in the recent People interview, Hopper was more lighthearted. also shared a very relatable dad detail: “My dad is really into FaceTime and texting. But when he texts, they’re like novels. He has to send them in increments. So I rarely read them!”
