Sean Penn’s Wives: Inside the Actor’s 3 Failed Marriages to Madonna, Robin Wright and Leila George

Sean Penn is now 0 for 3 when it comes to marriage. The actor and his current wife, Leila George, have called it quits just more than a year after tying the knot in July 2020. She filed for divorce from the Oscar-winning actor, making him three-times unlucky when it comes to wedded bliss.

The Milk star’s first wife was none other than superstar Madonna. The pair met in 1985 on the set of the singer’s “Material Girl” music video. He was a talented up-and-coming actor and she was the hottest new act in music. After just six months of dating, the pair tied the knot in a white wedding ceremony in Malibu on August 16, 1985, which was also the singer’s 27th birthday.

Sean and Madonna tried their hand at collaborating on the big screen, with the singer attempting to channel her Desperately Seeking Susan success. However, their 1986 film, Shanghai Surprise, turned out to be a critical and box office bomb. But the two were still madly in love, with Madonna dedicating her 1986 True Blue album to her husband. The pair’s marriage began to fail amid accusations of jealousy and infidelity, as well as the demands of her massive fame. They divorced in 1989.

On the heels of his split from Madonna, Sean became in involved with actress Robin Wright in 1989. They welcomed their first child, daughter Dylan Frances, less than two years later in 1991. The couple added to their family in 1993 with the birth of son Hopper Jack.

Despite having children, Sean and Robin’s relationship was tumultuous, with several break-ups and make-ups before the pair finally wed in 1996. The marriage ran hot and cold, with the pair announcing their plans to divorce in 2007 but withdrawing the petition four months later. The pair eventually split for good in 2010, making good on their divorce intentions.

Sean and Leila began dating in 2016, despite a more than 30-year age difference. She’s the daughter of Sean’s fellow acting peer, Vincent D’Onofrio, who is only one year older than the Mystic River star. The pair tied the knot at home in 2020 amid the COVID-19 lockdown. Currently, it’s unclear the reason for the couple’s split and Leila’s divorce filing. The two doi not have any children.

Scroll down for photos of Sean with his three wives.