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Sean Penn and Madonna Were an Iconic Couple In the 80s — Why Did They Divorce?

Edduin Carvajal
Apr 21, 2021
06:05 A.M.
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Before Brad Pitt and Angelina Jolie, Sean Penn and Madonna were the power couple in Hollywood. Their relationship, filled with accusations of infidelity and violence, was far from perfect.


Penn and Madonna tied the knot on August 16, 1985, the same day the singer turned 27 years old and one day before the actor’s 25th birthday, at one of his friends' seaside Malibu home.

Things were rocky from the get-go as Penn, famous for his heated temper, supposedly fired a gun at the helicopters that some photographers rented to get photos of the event.

Madonna and Sean Penn in August 1986 in New York City | Photo: Getty Images



Almost immediately after tying the knot, reports of a possible breakup were everywhere, especially because the “Mystic River” star kept getting involved in altercations with the press and his wife.

The fact that he was “jealous and insecure” didn’t help much. In April 1986, Madonna and songwriter David James Wolinski were at a Los Angeles nightclub hanging out as friends.


As he said goodbye, Sean Penn thought he was kissing Madonna, so he reportedly beat the musician up. He ended up with a $1,7000 fine and was sentenced to one year of probation.

Apart from that, Penn thought Madonna was having an affair with singer and model Nick Kamen. While she denied it, Penn was “wildly jealous.” According to Madonna’s great-aunt, Penn was "insanely jealous of her."

Sean Penn and Madonna on August 13, 1986 at the Mitzi Newhouse Theatre, Lincoln Center, New York City | Photo: Getty Images


It appears Madonna had known they wouldn’t be together for long. Before getting married, she said in an interview that they were so similar to each other and had so many things in common that he’s “almost like my brother.”

The singer, whose friends and family members reportedly disliked Penn, confessed that their temperaments were too alike, noting that it doesn’t always make for ideal relationships.

He allegedly physically abused the singer for almost ten hours.



In 2018, former tennis player John McEnroe shared some details on Penn and Madonna’s relationship during an interview with Graham Bensinger on his show.

McEnroe admitted that he used to think that his own relationship was volatile, but after seeing the former couple at a dinner, he felt comfortable as theirs was even more.

Sean Penn on March 29, 2018 in Philadelphia, Pennsylvania | Photo: Getty Images


After saying they never threw punches in front of him, McEnroe pointed out that Penn was a “very intense person.” He added that, at the time, what they did seemed normal, but not that much in retrospect.

It was also in 2018 that, when asked on “The Late Show with Stephen Colbert” to pick between Madonna and Britney Spears, Penn said he loves his first wife very much.



In December 1987, the former couple announced that they were parting ways, but they didn’t file for divorce. Things got disproportionally out of control exactly one year later when Penn moved out of their Malibu home following an argument.

On December 28, Penn reportedly returned home “drunk and irrational” and burst into the place. He allegedly physically abused the singer for almost ten hours, even tying her to a chair.

Sean Penn on January 5, 2019 in Los Angeles, California | Photo: Getty Images


Eventually, Madonna persuaded him to release her, and she never pressed charges. So far, neither Penn nor Madonna has commented on the incident publicly, but she filed for divorce on January 5, 1989.

In 2015, Penn got involved in a defamation case against “Empire” co-creator Lee Daniels. The latter had defended his show's star, Terrence Howard, against the backlash that followed his admission to hitting his wife.


Daniels said Howard had done nothing different than "Marlon Brando or Sean Penn," but people reacted more aggressively to Howard’s incident because “he is Black.”

Consequently, Penn issued a $10 million defamation suit against Daniels. The “Like a Virgin” singer also denied that she was ever struck by the actor during their time together. Sean Penn and Madonna’s relationship is unique, to say the least.

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