The Real Reasons Madonna And Sean Penn Got Divorced

Madonna and Sean Penn were a match made somewhere far from Heaven. Their relationship was rife with accusations of infidelity, domestic violence, and general discord. They're good friends now, but the slew of reasons for their breakup—some minor, some major—would've made it understandable if they never spoke again.

Madonna predicted the divorce in an interview before they got married, noting that they were almost too alike, which, as any couple whose shared traits include fiery tempers, strong egos, and stubbornness can tell you, may not make for a lasting marriage. "We have so much in common that he's almost like my brother," Madonna told People. "His temperament is also similar to mine. That doesn't always make for ideal relationships, but I don't know what will happen."

A big sign the person you're with isn't 'The One'? Your buddies all hate him. Case in point: A source close to the Queen of Pop told People that many of her close friends and family members "disliked Sean. They saw him as spoiled and immature and were amazed by his drinking and temper tantrums."

Madonna was trying to break into movies around the time she and Penn were together. Their collaboration, Shanghai Surprise (1986) was labeled a disaster, with one reviewer writing, "Madonna's incompetent performance secured her reputation as a no-talent actress...and, to date, she still hasn't been able to shake that reputation." The movie only had $2 million in ticket sales and a $17 million budget, meaning audiences loved it as much as critics did... which is to say, not at all.

A source close to Madonna told People, "She wanted the marriage to work. All the jokes about the marriage motivated her to work hard at making the marriage go. I don't think she considered him in terms of her career."

Penn's jealous streak may have been a veritable kiss of death for his marriage, because he was dating one of the biggest pop stars on the planet. In April 1986, Madonna was at a nightclub with pal David James Wolinski, a songwriter. People reports that Wolinski was saying goodbye to Madonna when Penn allegedly clocked him... because he thought they were kissing. Penn packed such a punch that he knocked Wolinski out of his seat. The future Oscar winner was fined $1,700 and sentenced to one year of probation for the blowup. It was far from his only scuffle during the relationship.

A friend of Madonna told People, "The marriage had been undergoing stress all the time, but this was the first major stress, the first really traumatic episode for her. Wolinski was someone she knew, and it really shook her up." Insiders told the magazine that Penn also believed Madonna was having another affair with singer-model Nick Kamen, which she denied, but still "made Sean wildly jealous."

Madonna's great-aunt told People, "It didn't seem like they got along...I'd say he was insanely jealous of her."

Perhaps part of why Penn was so suspicious and jealous of Madonna is because he was projecting—because he developed quite a reputation for being a ladies' man after they split. During his on-again-off-again relationship and marriage with Robin Wright, who he began dating shortly after his divorce from Madonna, he also had relationships with Jewel, Petra Nemcova, Elle Macpherson, Jessica White and Natalie Portman.

He and Wright divorced for good in 2010; he briefly hooked up with Scarlett Johansson in 2011, then gorgeous non-celeb Shannon Costello. He was madly in love with Charlize Theron, but she dumped him. As of October 2016, he was dating actor Vincent D'Onofrio's 24-year-old daughter. Classy!

In July 1985, Penn was accused of attacking two freelance photographers with a rock and ordered to pay two $50 fines. While filming Shanghai Surprise (1986) in 1986, Penn was accused of attempted murder, arrested, and jailed—but escaped and was eventually pardoned. In June 1987, he was busted for a DUI and days later arrested for allegedly attacking an extra who he believed tried taking a picture of him and his Colors (1988) co-star Robert Duvall on set; the extra was hospitalized for his injuries. He pleaded his DUI down to reckless driving and was sentenced to 60 days in jail and two years of probation for the combination of offenses.

Perhaps all those legal troubles served as a series of red flags for Madonna.

Between their busy careers and Penn's time spent behind bars, Penn and Madge didn't see each other very often. Unfortunately, absence didn't make the heart grow fonder. A source told People the couple began fighting more often when he got out of prison, leading a pal to suggest a trial separation. Madonna reportedly replied, "We're separated all the time, and it doesn't make it any better."

This was probably a big reason for the breakup if true: Penn has been accused for years of brutally assaulting, kidnapping, and sexually abusing Madonna when they were still married back in 1987. The Daily Mail reports, "In June 1987, Madonna went to the Cedars Sinai hospital [in Los Angeles] for an X-ray after Penn apparently hit her across the head with a baseball bat." Penn was claimed to have bound and gagged his then-wife, who was rendered "unrecognizable" from the alleged beating.

In 1991, Penn told Playboy (via Gawker) that authorities came to their home. "A SWAT team surrounded my house and came in every door. But it happened because on the day that we split up, she developed a concern that if she were to return to the house, she would get a very severe haircut... So she took this concern to the local authorities, who came back up to the house," he said. "She felt the responsible thing to do would be to inform them—since they were coming up there ostensibly to keep her from getting a haircut and to let her gather some personal effects—that there were firearms in the house...No charges were ever filed."

There isn't much evidence to corroborate the abuse allegations, but Gawker compiled a litany of articles and sources claiming the traumatic events did happen. Penn and Madonna would later both adamantly refute the allegations...but Madonna was vague when asked if she filed a police report about it.

Penn went as far as to file a $10 million lawsuit against Empire creator Lee Daniels for defamation of character for bringing up the allegations in the press...and Madonna supported him in it in court documents.

"I am aware of the allegations that have surfaced over the years accusing Sean of incidents of physical assault and abuse against me," she said in his court documents (via The Daily Beast). "Specifically, I am aware of the allegations concerning an alleged incident that occurred in June 1987, whereby (according to tabloid reports), Sean allegedly struck me with 'a baseball bat.' I know the allegations in those and other reports to be completely outrageous, malicious, reckless, and false. I am also aware of allegations concerning an incident that occurred in December 1989, which purportedly resulted in Sean's arrest for domestic assault and battery against me. I know those allegations to be false. While we certainly had more than one heated argument during our marriage, 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."

As if Penn's colorful history of paparazzi freakouts wasn't enough proof that he can't handle the spotlight, he said as much himself in an Esquire interview in 2015. "When I got in [the business] I was really culture shocked...Paparazzi. I had a lot of that s**t because of my first marriage," he said. "I always try to suggest to people, forget they have a camera. You're looking at it saying, that camera's following some rich person, that's the price of fame. But if you're willing to consider that the people they are following are human beings, take the camera out of their hands. Just be followed every day all day by somebody. At some point, you might consider homicide, forget about punching somebody in the face. You want your life! And people usually get it when you put it in those terms."

In a rambling interview with Esquire from 2015, when Penn was engaged to Charlize Theron, he revealed that he didn't even really believe his first two marriages—to Madonna and to Robin Wright—counted. Seriously?

"I'm very friendly with my first ex-wife. I would say that I'm on extremely good terms with the children I share with my second ex-wife," he said. "Initially, in a divorce, you kick and bite about the other person. But finally you're looking at your failures to that person, to a marriage, to a friendship, to yourself during that time as well. Because no matter what the other person was or wasn't, for better and for worse, it really has so little to do with the growth you need to find better circumstances. Almost exclusively it has to do with your own stuff." He added, "You say I've been married twice before but I've been married under circumstances where I was less informed than I am today," he said, "so I wouldn't even consider it a third marriage, I'd consider it a first marriage on its own terms if I got married again."

Wow. We're sure Madge and Wright were really flattered to hear that.