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Sean Penn | Hopper Penn, Sean Penn, and Dylan Frances Penn | Sean Penn and Leila George | Source: Getty Images | www.youtube.com/user/CNN
Sean Penn | Hopper Penn, Sean Penn, and Dylan Frances Penn | Sean Penn and Leila George | Source: Getty Images | www.youtube.com/user/CNN

Sean Penn Decided to Change & Prioritize His Kids — He Regrets Divorce from the Woman He Still Loves

Wian Prinsloo
Nov 13, 2022
02:00 P.M.

Sean Penn's alcoholism cost him his marriage with Leila George. The two got married over Zoom in 2020 due to the pandemic. Despite the divorce, he still loves her. After losing Leila, he started devoting his time to his children.

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Sean Penn was born in Santa Monica, California, on August 17, 1960. With parents who were also entertainers and performers, Sean was destined for a career in acting. But, instead of going the classical route of college, the actor chose a more hands-on approach.

He started at the Los Angeles Repertory Theater, where he learned the ropes. In 1980, he decided to make the leap and try his luck in New York, where he garnered some fame in theatre productions. This opened many doors for Sean, and soon he got a part in "Fast Times at Ridgemont High."

Sean Penn speaks onstage at the Cinema For Peace event benefitting J/P Haitian Relief Organization in Los Angeles held at Montage Hotel on January 14, 2012 in Los Angeles, California | Source: Getty Images

Sean Penn speaks onstage at the Cinema For Peace event benefitting J/P Haitian Relief Organization in Los Angeles held at Montage Hotel on January 14, 2012 in Los Angeles, California | Source: Getty Images

The Cannes Best Actor award winner seemed to be on his way to greatness, but after 1985, things took a slight turn. He married Madonna, and while they were together, several encounters with the paparazzi turned violent. The actor spent a month in jail in 1987, and a year later, he broke off his marriage to the pop icon.

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He would get up at four in the morning and watch the news with vodka, tonic, and Ambien until Leila woke up.

Luckily, the actor managed to get back on his feet. Not only did he star in more movies that added to his reputation, but he also tried his hand at directing. He wrote and directed the films "Indian Runner" and "The Crossing Guard." In 1996, he received his first of many Academy Awards for the film "Dead Man Walking."

Sean Penn acceptance speech for Best Actor Award during The 76th Annual Academy Awards, February 29, 2004 - Show at The Kodak Theater in Hollywood, California, United States | Source: Getty Images

Sean Penn acceptance speech for Best Actor Award during The 76th Annual Academy Awards, February 29, 2004 - Show at The Kodak Theater in Hollywood, California, United States | Source: Getty Images

Sean has always been an avid political activist and has attracted much controversy for some of his political views. Besides acting and directing, he has also written a book called "Bob Honey Who Just Do Stuff." The novel is a satire focusing on the life of a divorced assassin.

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Sean Gave Marriage Another Try

Despite his professional successes, Sean wasn't as lucky in romantic relationships. After Madonna, the actor married actress Robin Wright in 1996, and they had two kids. They decided to split up in 2010. Then, in 2013, Sean started dating the South African-born actress Charlize Theron. Although they weren't married, they were close.

As he grew older and learned more about parenting, Sean has worked on how he treats his kids and has tried to be a better father.

In 2015, though, Sean and Charlize also decided to go their separate ways, leaving the actor alone once more. But he wouldn't be on his own for long. In 2016, he started dating the "Mortal Engines" star, Leila George. After four years together, Sean and Leila decided to tie the knot in 2020.

Robin Wright-Penn and Sean Penn during The 76th Annual Academy Awards, February 29, 2004 Hollywood, California, United States | Source: Getty Images

Robin Wright-Penn and Sean Penn during The 76th Annual Academy Awards, February 29, 2004 Hollywood, California, United States | Source: Getty Images

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During the Covid-19 pandemic, Sean and Leila wanted to get married, and they were tired of waiting for everything to return to normal. Instead, on July 30, 2020, the two gathered the few people quarantining with them around a computer, and found someone to officiate. Sean explained:

"It was Thursday. We did a COVID wedding. By that I mean it was a county commissioner on Zoom and we were at the house, my two children and her brother. And we did it that way."

Unfortunately, the marriage didn't last very long. In 2021, Leila filed for divorce, and Sean was heartbroken. The actor admitted he was not exactly the perfect partner when they were together. He would get up at 4 a.m. and watch the news with vodka and Ambien, and greet Leila with a nonchalant, "Good morning, honey."

Sean Penn and Leila George arrive at the "Meet Me In Australia" event benefiting Australia Wildfire Relief Efforts at Los Angeles Zoo on March 08, 2020 in Los Angeles, California | Source: Getty Images

Sean Penn and Leila George arrive at the "Meet Me In Australia" event benefiting Australia Wildfire Relief Efforts at Los Angeles Zoo on March 08, 2020 in Los Angeles, California | Source: Getty Images

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After their divorce, the actor realized how he neglected his ex-wife. He knew that he still loved her and saw that his lifestyle at the time was not conducive to a healthy relationship. He decided he needed to change how he lived to prioritize his family. He still saw Leila often, meaning he could still prove himself.

Sean Worked On His Relationship with His Kids

Sean also shares two children with his second wife, Robin. His daughter, Dylan Frances Penn, is the oldest and was born on April 13, 1991. She is interested in fashion and has worked with prominent publications, such as "Elle" and "GQ." She started working on her career in acting in 2015. After accompanying her father to Cannes Film Fest, she posted:

"Last night was a dream. Thank you to everyone who made this possible! I am forever grateful."

Sean's second child, Hopper Penn, also followed in his father's footsteps and has a few films to his name. Although he now has a good relationship with his father, the two didn't always get along. Hopper shared that when he was younger, he often got into trouble, which didn't help the situation.

Sean Penn, Hopper Jack Penn, Dylan Frances Penn and Robin Wright Penn Attend Atlanta Hawks vs. New York Knicks Game, 2004 | Source: Getty Images

Sean Penn, Hopper Jack Penn, Dylan Frances Penn and Robin Wright Penn Attend Atlanta Hawks vs. New York Knicks Game, 2004 | Source: Getty Images

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Sean's son also mentioned that things changed as they both grew older. Hooper saw his dad in a new light when Sean helped out in Haiti after the earthquake in 2010. He said that he saw a side of Sean that he had never seen before, which made him respect his dad even more:

"I'd never seen that side of him. It was just immediate, and he was really smart with it. Emergency mode is his place. I feel like he's the calmest when chaos is going on. It's really great."

As he grew older and learned more about parenting, Sean has worked on how he treats his kids and has tried to be a better father. He focused on being more present while spending time with his family. He even started ignoring his phone to enjoy their company without distractions.

Jadyn Rylee, Katheryn Winnick, Dylan Penn, Dylan Frances Penn, and Sean Penn and attend the "Flag Day" screening during the 74th annual Cannes Film Festival on July 10, 2021 in Cannes, France | Source: Getty Images

Jadyn Rylee, Katheryn Winnick, Dylan Penn, Dylan Frances Penn, and Sean Penn and attend the "Flag Day" screening during the 74th annual Cannes Film Festival on July 10, 2021 in Cannes, France | Source: Getty Images

Hopper also said that his father has been making an effort to communicate when they can't see each other in person. He shared that his dad enjoys Facetiming his kids to catch up when he can't visit. Sean apparently sends texts with updates that can fill a tome to stay close to his kids.

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