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Sean Penn’s Past Marriages: Everything To Know About His 3 Past Wives, Including Madonna

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Sean Penn’s Past Marriages: Everything To Know About His 3 Past Wives, Including Madonna

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Image credit: Jim Smeal / Shutterstock

Actor Sean Penn62 years old, has repeatedly found love with some of Hollywood’s most famous ladies. And although he is best known for his roles in hit movies like Milk, I’m Samand InterpreterSean is also the leading man in his three ex-wives. Keep reading to meet the women who have called Sean their husband over the years.


Madonna and Sean Penn
Madonna and Sean Penn were married from 1985 to 1989. (Jim Smeal / Shutterstock)

Pop music icon Madonna, 64 years old, famously married Sean in 1985, at the height of her music career. Sean and the “Like a Virgin” singer were married for 4 years until the famous couple decided to break up. On December 4, 1987, Madonna filed for divorce from Sean before withdrawing the papers just 12 days later, according to Today in Madonna’s history. It seemed all was back on track until the pop queen filed for divorce again on January 5, 1989. In the filing, she cited “irreconcilable differences”, was the reason for the breakup.

Nearly 30 years later in 2016, Madonna and Sean appeared together in Miami at her charity gala held at Art Basel. At the event, Madonna said “I still love you”, to her ex-husband of 27 years. At the time, Madonna and Sean auctioned off some of their black and white wedding photos for charity. It’s great to see that there is no love lost between these two!

Robin Wright

Robin Wright and Sean Penn
Robin Wright and Sean Penn were married from 1996 to 2010. (Chris Pizzello/AP/Shutterstock)

After breaking up with Madonna, Sean continued to get married Princess Bride star Robin Wright56 years old, seven years later in 1996. His marriage to Robin was his longest, as the couple were together for a total of 14 years before divorcing in 2010. And although the former couple was broke up 12 years ago, they have remained together since they share two children together.

Before getting married, Robin and Sean welcomed their daughter Dylan Penn31 years old in 1991 and then welcomed their only son, Dance Penn29 years old in 1993. Since the breakup, Robin has moved on to marry her 38-year-old husband. Clement Giraudet. Her first husband, Dane Witherspoonsadly passed away in 2014 at the age of 56.

Leila George

Leila George and Sean Penn
Leila George (L) and Sean Penn were married from 2020 to 2022. (Vianney Le Caer / AP / Shutterstock)

Sean finds love for the third time when he gets married Leila George30, in 2020. The Milk the actor also dated an Oscar winner Charlize Theron, 47 years old, from 2013 to 2015, before meeting Leila. His marriage to Leila came after they were said to have dated for about 4 years, short and sweet as the former couple ended their marriage in October 2021.

It was the Australian actress who filed for divorce in Los Angeles at the time, just a year after they got married. Sean and his ex had a virtual Zoom wedding during the initial COVID-19 lockdown in 2020. Then, in June 2022, just two months after they finalized their divorce, Sean and Leila was spotted eating out together in Santa Monica. After all, some divorces will have a happy ending!

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Sean Penn’s Past Marriages: Everything To Know About His 3 Past Wives, Including Madonna

I am passionate about journalism and using new technology to spread news. I am also interested in politics and economics, and I am always looking for ways to make a difference in the world. I am the CEO of Janaseva News, and I am 24 years old.

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