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In the late ’80s, Madonna and Sean Penn were among the most notable celebrity couples in Hollywood. While he was one of America’s hottest young actors at the time, she was a successful rocker with the most famous black bra in the world. From an outside perspective, the pair were a match made in heaven and practically unstoppable together.

However, soon after tying the knot, the couple found their marriage rife with issues, which ultimately led to the demise of their relationship.

Madonna and Sean Penn
Madonna and Sean Penn | Steve Granitz/WireImage

Sean Penn was the love of Madonna’s life

Madonna and Sean Penn’s love story began in 1985 after meeting on the set of the singer’s “Material Girl” music video. Since both had just gotten out of relationships, they started off as friends, dating non exclusively.

However, their relationship soon blossomed into a full-on romance.

After just six months together, Madonna and Penn tied the knot in August 1985 on her 27th birthday.

Following their nuptials, Madonna and Penn’s romance played out in the public eye with the pair starring together in the 1986 adventure comedy Shanghai Surprise and the singer dedicating her 1986 True Blue album to her new husband.

Madonna and Sean Penn
Madonna and Sean Penn | Brenda Chase/ Getty Images

To onlookers, it seemed like Madonna and Penn were perfect together and had a long and happy marriage ahead of them.

But behind closed doors, the couple’s marriage was rife with accusations of infidelity, domestic violence, and general discord — all of which seemingly led Madonna and Penn’s romance down a dark path that ended with divorce.

Jealousy and insecurities put a strain on Madonna and Penn’s relationship

Though their relationship started out great, it deteriorated shortly after their wedding due to Penn’s unpredictable outbursts and temper tantrums.

According to insiders, the actor had a major jealous streak and would often fly off the hinges when he saw other men getting close to Madonna.

One of the earliest reports of this happening occurred in April 1986, when Penn attacked songwriter David Wolinski in a nightclub after he thought Wolinski was kissing Madonna.

“The marriage had been undergoing stress all the time, but this was the first major stress, the first really traumatic episode for [Madonna],” a source told People at the time. “Wolinski was someone she knew, and it really shook her up.”

The future Oscar winner was fined $1,700 and sentenced to one year of probation for the blowup.

Insiders also told the magazine that Penn believed Madonna was having an affair with her “Each Time You Break My Heart” collaborator Nick Kamen. Though she denied cheating on Penn with Kamen, seeing them together “made Sean wildly jealous.”

But despite his insecurities, Madonna was understanding of Penn’s actions and even revealed that she too has those moments.

“I have my insecure moments,” Madonna admitted at one point during the relationship, “and that puts a lot of strain on people. You take things out on the person you love, and that causes fights, alienation, grief, shrink sessions and a lot of ca-ca.”

Inside the abuse rumors

In December 1987, Madonna filed for divorce from Penn but later withdrew the papers, only to file them again in January 1989.

While it’s unclear if Penn’s outbursts prompted the singer to end their relationship, it’s been rumored that the singer suffered years of abuse from her husband, which many believe was a big reason for their split.

However, it turns out those rumors were not true. Madonna even set the record straight on the abuse accusations in 2017, insisting that Penn never laid a hand on her during their marriage.

Madonna and Sean Penn
Madonna and Sean Penn, | Kevin Winter/Getty Images

Maybe the 3rd Time’s the Charm for Sean Penn

“I am aware of the allegations that have surfaced over the years accusing Sean of incidents of physical assault and abuse against me,” the singer claimed, according to 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.”

She continued, “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.”

While the reason behind their split remains a mystery, insiders previously hinted to People that constant separation as well as the couple’s work schedules played a part in their marriage ending.

The pair never stopped loving each other

Although Madonna and Penn’s marriage came to a tumultuous end in 1989, they have continued being great friends in the years following.

Not only have they support each other’s respective careers, they’ve also spoken highly of one another during interviews and special events.

In 1991, Madonna released her documentary In Bed With Madonna, where she was asked to name the love of her life. She coyly whispered back one single word: “Sean.”

In 2015, Penn was spotted attending two nights of Madonna’s Rebel Heart. Three years later, he revealed on The Late Show With Stephen Colbert that he still loves her ex-wife “very much.”