Maybe the 3rd Time’s the Charm for Sean Penn

There is always some A-list celebrity in the headlines because they recently tied the knot. Some marry partners far younger, and some are on their second or third marriage. Sean Penn is one of these celebrities. He recently confirmed rumors that he was married again–for the third time. His wife also happens to be over 30 years younger than him. We’re hoping–for both their sake–that this marriage turns out better than his first two. 

(L-R) Sean Penn and Leila George smiling in front of a white background with black and red logos
(L-R) Sean Penn and Leila George | Rodin Eckenroth/Getty Images

Was Sean Penn married to Madonna? 

In 1985, Sean Penn married for the first time. His first wife was none other than the Material Girl herself, pop legend Madonna. The pair was one of the hottest couples in Hollywood, but their marriage hit a really rocky spot and they divorced in 1989. 

Their divorce was a nasty one, with rumors swirling about domestic abuse. There were accusations of violent abuse in 1987 and 1989, but both Penn and Madonna later denied that any such abuse occurred. Madonna later defended him in court documents, as reported by Marie Claire:

“I know the allegations in those and other reports to be completely outrageous, malicious, reckless, and false. I am also aware of allegations concerning an incident that occurred in December 1989, which purportedly resulted in Sean’s arrest for domestic assault and battery against me. I know those allegations to be false.”

There were plenty of other reasons behind the couple’s divorce. Penn had a lot of legal issues–he was arrested a few times, for issues from DUIs to assault, according to LA Times. Between his time spent in jail, and both star’s busy careers, they certainly didn’t have a lot of time to put into a marriage. Madonna’s friends also said Penn was incredibly jealous and insecure. 

Despite all of these issues, the two remain close to this day. Penn recently said that he still loves his first wife very much, according to ET. In 2016, while the two were working on a charity event, Madonna said she was still in love with Penn. 

Who does he have kids with? 

RELATED: How Many Times Has Madonna Been Married?

In 1996, Penn married his second wife, Robin Wright. The two began dating shortly after Penn’s divorce from Madonna, and their relationship was fairly rocky, according to Popsugar. Some speculate that Wright had a hard time with Penn’s fame–she was trying to make a name for herself and was possibly feeling overshadowed by Penn’s success. 

The couple eventually moved in together, and Wright was soon pregnant with their first child. Their daughter Dylan was born in 1991, and their son, Hopper, was born two years later. Wright had put her career on hold for a while to take care of their family, but in 1994 she delivered a fantastic performance as Jenny in the film Forrest Gump. Her performance earned her a Golden Globe nomination for Best Supporting Actress. 

Wright’s career began to slow down again, and the couple had decided that Penn would continue to work (since he earned far more money) and she would focus on their family. She didn’t ditch her career entirely, though, and the pair collaborated on a few projects. They moved to San Francisco in an effort to escape the public eye and have a more stable place to raise their children. 

The move wasn’t enough to save the marriage, and Wright filed for divorce in 2007. A few months later, however, she withdrew the petition and the couple was back together. In 2010, they gave up for the last time, and decided to divorce. 

Who is his new wife? 

Last month, Penn confirmed that he had gotten married again. His third wife is 28-year-old Leila George, daughter of actor Vincent D’Onofrio and actor Greta Scacchi, according to USA Today. George is an actor and a philanthropist. The pair has been seen attending charity events and George is also very involved in Penn’s nonprofit, Community Organized Relief Effort. 

Penn says they had a “COVID wedding,” which means very few people were in attendance. They were married over a Zoom meeting, with only George’s brother and Penn’s two children at the house with them. Penn wasn’t very disappointed about the lack of a big wedding. In an appearance on Seth Meyer’s late-night show, Penn jokingly said “Let’s say there are socially-liberating factors under COVID.”