Monday, June 22, 2026

Sean Penn, Almost 60, Marries Vincent D’Onofrio’s 28 Year Old Daughter, His Kids Are 29 and 27 So She Fits Right In

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Congrats to Sean Penn. He’s taken his third wife. The 59 year old Oscar winner has married Leila D’Onofrio, the 28 year old daughter of actor Vincent D’Onofrio. I will not make a joke about “Criminal Intent.” Or “Law and Order.”

Penn has two children. Daughter Dylan is 29. Son Hopper will be 27 next week. So Leila will have a lot in common with them. That’s important because as Sean turns 60 on August 17th, I know from personal experience that naps are needed and so refreshing. The three young people can entertain each other.

In Hollywood, this sort of thing is the norm. Dennis Quaid just married a young woman– his third or fourth wife– who is about the same age as his son, Jack. I saw Dennis and his then fiancee backstage in 2019 at Willie Nelson tribute and he didn’t look so great. Having a young woman around can be a help and hindrance. At 66, Quaid is 39 years older than his wife, whose name doesn’t matter.

Sean has done incredible philanthropic things, especially with Haiti. He’s also got a long line of memorable acting credits including “Mystic River,” for which he won that Oscar.

How does D’Onofrio feel? He just turned 61 in June. Will he call Sean ‘dad’? How does Madonna feel? Sean’s first wife is 61 herself, almost 62. But her boyfriends are selected from foundling hospitals. So she will send Champagne.

PS Sean’s marriage was not announced in the New York Times, but by Hollywood seer Irena Medavoy, the great wife of beloved producer Mike Medavoy. She refers to Penn as “being like a son” to Medavoy, which is pretty nice. So there’s that.

 

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Roger Friedman
Roger Friedman
Roger Friedman is the founder and editor-in-chief of Showbiz411. He wrote the FOX411 column on FoxNews.com from 1999 to 2009, where he covered Michael Jackson, and previously wrote the "Intelligencer" column at New York magazine in the mid-1990s, where he covered the O.J. Simpson trial. He also edited Fame magazine. His bylines have appeared in The New York Times, The Washington Post, the New York Daily News, the New York Post, Vogue, Details, and the Miami Herald. He is a voting member of the Critics Choice Awards (Film and Television branches), and his movie reviews are tracked by Rotten Tomatoes. With D.A. Pennebaker and Chris Hegedus, he co-produced the 2002 documentary "Only the Strong Survive," which screened at Directors' Fortnight at the Cannes Film Festival.

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