Inside Madonna's Complicated History With Sean Penn

This article includes discussions of domestic abuse.

Madonna and Sean Penn undoubtedly had one of the most chaotic marriages in Hollywood history. The legendary singer first met the future Oscar winner when he played a small part in her 1985 music video for "Material Girl." Speaking to Cosmopolitan in 1987, Madonna revealed that she could envision a future with Penn pretty much from the moment she first laid eyes on him. So, the pop star tried to make that dream a reality by playing it coy and eventually striking up a conversation with him on the overly crowded set. While Madonna had presented flowers to everyone who helped with the music video, she hand-delivered a rose to her future beau.

During a 1985 chat with People, she gushed about the "Mystic River" star, "We have so much in common that he's almost like my brother." The "Vogue" hitmaker continued, "His temperament is also similar to mine. That doesn't always make for ideal relationships, but I don't know what will happen." Of course, by then, they had already taken their relationship to the next stage. Speaking to Interview Magazine, Madonna shared that she was going about her morning routine as usual when she got a strong feeling that Penn wanted to propose to her simply because of a "look in his eye," per The Times. 

The Grammy winner informed him that she was on the same page, so he officially asked her to marry him. The A-listers tied the knot in a private but star-studded ceremony in August 1985, just six months after they first met.

In July 1986, the Los Angeles Times reported that a battery count had been filed against Sean Penn for allegedly physically assaulting David Wolinski. According to the former Rufus member's account, the assault took place at a nightclub in April 1985. As Wolinski was leaving the A-list couple for the night, Penn started to believe that he had tried to lock lips with his wife and reportedly struck him in the face and kicked him. The "21 Grams" star also supposedly tried to hurl furniture at Wolinski before other patrons came to his rescue. At the time, an insider informed People that the "Like A Virgin" hitmaker was gravely affected by the alleged assault, admitting, "The marriage had been undergoing stress all the time, but this was the first major stress, the first really traumatic episode for her." 

They continued, "Wolinski was someone she knew, and it really shook her up." Although Penn later pleaded not guilty to the charge, he ultimately had to shell out $1,700 in fines and also was put on probation for a year. Later, an insider informed People that the Oscar winner was similarly displeased by Madonna's close working relationship with Nick Kamen too. As the duo worked on his track, "Each Time You Break My Heart," Penn started spiraling that they were having an affair. Although Madonna reassured him nothing was going on, a source claimed that Penn still "caused a lot of problems in the studio."

Christopher Andersen's 1991 biography "Madonna Unauthorized" painted a dark picture of her marriage to Sean Penn. The author claimed that the controversial star was utterly consumed by the idea of his A-lister wife cheating on him. Penn's jealousy was the center of many of their biggest fights and would often cause him to allegedly physically abuse Madonna. After one particularly explosive argument, the "Dead Man Walking" star even went away to live with his parents for a bit and supposedly started filling the singer's inbox with vile messages. Penn went out drinking a few days later and then allegedly barged his way into Madonna's house, tied her up with twine, and physically abused her while she was bound to a chair. Eventually, the pop star convinced him to set her free, and she managed to call for help in her car. 

When the police arrived, Penn claimed that the pop star had created the story to tear into him for getting into a relationship with an exotic dancer. Additionally, there were several reports at the time of Penn hitting his then-wife with a baseball bat. It's worth noting that the "Milk" actor and Madonna have both denied his alleged physical abuse to this day. Amidst Penn's $10 million defamation lawsuit against filmmaker Lee Daniels in 2016, the "Holiday" hitmaker submitted a legal declaration, in which she asserted, "Sean has never struck me, 'tied me up,' or physically assaulted me, and any report to the contrary is completely outrageous, malicious, reckless and false," per Billboard. Penn similarly denied the allegations during his 2024 chat with the New York Times and also firmly stated, "[Madonna's] someone I love."

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Madonna first filed to end her marriage with Sean Penn in 1987. As rumors about the reasons for their split started flying, a spokesperson for the "Crazy For You" songstress offered some clarity to People, reasoning, "There was no one direct incident leading up to this." They elaborated, "It was a series of cumulative pressures. There were many moments in their marriage when it was shaky, and Madonna was finally forced to face the reality of the situation — that they weren't happy together." Another confidant insisted that the music icon desperately wanted their Hollywood union to go the distance because the media was so plagued with stories about how they would divorce in no time. Ultimately, though, Madonna withdrew her filing only a fortnight later. 

Then, she filed for divorce again in 1989. At the time, a rep for the actor told the New York Times that their split was "amicable." But in "Madonna Unauthorized," Christopher Andersen claimed that the filing came a week after her then-husband allegedly broke into her home. He also noted that the "Beautiful Stranger" hitmaker officially dropped the complaint she had filed against her soon-to-be ex-husband for his alleged abuse shortly after filing to dissolve their marriage. Additionally, The Times reported that Madonna acknowledged that she had always been a bit of a rebel when it came to societal standards so she couldn't be the traditional "nurturing" wife that her hubby so badly wanted. Penn and Madonna ultimately signed off on their divorce papers a few weeks later.

Speaking to O, The Oprah Magazine, in 2005, actor Sean Penn confessed that the end of his marriage to Madonna brought with it a sense of relief. "It was a good thing. Well, it was a miserable marriage, but I like her a lot," Penn remarked. "It got me steps further and clearer into knowing what I wanted. I still had a lot of demon doors to go through." In fact, as the Oscar winner disclosed of their tumultuous relationship, "I don't recall having a single conversation in four years of marriage." In fact, the "Sweet and Lowdown" star couldn't recall much about that period in his life at all, other than that he was a heavy drinker. 

Still, Penn didn't view their marriage as a waste of time because he learned a lot from it. There's a small chance that one of the many lessons the actor took away was to avoid sharing the screen with your spouse. Shortly after Penn and Madonna tied the knot, they joined forces for the 1986 comedy flick "Shanghai Surprise." On paper, it seemed like a good idea to get one of Hollywood's power couples together for a movie. Unfortunately, in reality, it turned out to be a disaster that led critics to question whether Madonna could even act. For her part, though, the pop icon shifted the blame onto the director and editors.

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Madonna was notably one of the many celebrities who attended Sean Penn's fundraiser gala for Haiti, "Sean Penn & Friends: Help Haiti Home," in January 2016. The legendary singer even took to the stage to perform her rendition of "La Vie en Rose" after sweetly sharing, "I want to say, Sean, I love you, from the moment that I laid eyes on you," per Variety. Shortly after the event, a source dished to Page Six that the former spouses had found their way back to each other. They stirred the pot further by claiming that Rocco Ritchie, the son Madonna had during her marriage to Guy Ritchie, wasn't a huge fan of Sean's and had decided to fly back to London to be with his father as a result of the reunion. However, Dylan Penn (Sean's director daughter with Robin Wright, who has naturally grown up to be gorgeous) clarified that her dad and Madonna were "really good friends."

And her account seemed more and more plausible as the years dragged on. For instance, during the Oscar winner's 2024 New York Times interview, Penn hinted that he was in a good place with Madonna by slyly confirming, "It turns out it's a lot quicker to repair a friendship after divorce if there are [no] kids involved." Meanwhile, the "Papa Don't Preach" songstress stayed true to herself and made a cheeky remark about her ex-husband during a December 2016 gala, saying, "I'm still in love with you" before offering to remarry him in exchange for $150,000 towards the fundraiser, per People. Still, given how much Madonna's relationship history has evolved since their split, it's safe to say she's over Sean.