Madonna has dated a number of celebrities, particularly in the early years of her career. The pop star was linked to Tupac, Warren Beatty, Jean-Michel Basquiat, and Dennis Rodman, among others.
But no one made as much of a lasting impression on the star more than the two most high-profile romances of her life: Sean Penn and Guy Ritchie.
Let’s take a look back at these two defining relationships for the Queen of Pop.
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Sean Penn: A rocky relationship
Madonna met actor Sean Penn in 1985 when she was 26 years old, while filming the music video for Material Girl. The pair hit it off instantly, and soon they were hanging out every day.
Things started out slow: they’d both just gotten out of relationships and wanted to stick to just being friends with benefits. The plan didn’t quite work, however, and they married just six months after meeting, on the pop star’s 27th birthday.
“We have so much in common that he’s almost like my brother,” she told People the month before their wedding. “His temperament is also similar to mine. That doesn’t always make for ideal relationships, but I don’t know what will happen.”
They lived their lives in the spotlight, constantly facing the scrutiny of media and fans. In 1986, they both starred in the film Shanghai Surprise. Later that year, Madonna released an album True Blue, dedicated to Penn.
Though they seemed like the picture of love and happiness, reports swirled that behind closed doors, there was trouble in paradise. Penn was allegedly very jealous, accusing Madonna of cheating on numerous occasions. Accusations of infidelity, domestic violence, and constant arguing between the two plagued the headlines in the late 1980s.
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In April 1986, Penn was charged after attacking songwriter David Wolinski in a nightclub, because he thought he saw him kiss his wife.
“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.”
Despite extensive reports of Penn’s jealousy and anger, Madonna backed up her husband.
“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.”
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In December 1987, Madonna filed for divorce, but withdrew the papers just two weeks later. She filed them again a year later, in January 1989.
The couple remained friends, however.
In 1991, in her record-breaking documentary In Bed With Madonna, the star named Penn as the “love of her life”. He’s been spotted attending her concerts over the years, and in 2017, he told Stephen Colbert that he still loves his ex-wife “very much”.
During a gala at Art Basel in 2016, Madonna said she was “still in love” with Penn, even offering to remarry him if he bid $150,000 in a charity auction.
Though were many rumours following the divorce that Penn was violent toward Madonna, but the singer quashed those allegations.
“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,” Madonna said in 2015.
Guy Ritchie
Madonna met Guy Ritchie, an English film director, in 1999 at a party hosted by their mutual friend Sting. At the time, Madonna had a two-year-old daughter, Lourdes, who she shared with her ex-boyfriend Carlos Leon.
It was attraction at first sight for the pop star. “I had a whole premonition of my life fast-forward,” she told People. “My head didn’t just turn, my head spun round on my body. I was taken by his confidence. He was sort of cocky but in a self-aware way… He’s a risk taker and he’s got a hungry mind.”
The media labelled him her toy-boy, as he was, at age 29, a decade younger than her.
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But Ritchie had made a name on his own. “Guy works almost as hard as Madonna does,” her friend and actor Rupert Everett said of the couple. “He’s definitely not a boy toy.”
It took a while for the relationship to get off the ground, as they were each so hyper-focused on their own careers and unwilling to compromise. He was also seeing TV presenter Tania Strecker at the time, while also hanging out with Madonna on the side.
But by the end of 1999, the singer relented, agreeing to move to London with her beau. Their son Rocco was born in August 2000, after a complicated pregnancy and birth.
Ritchie proposed to his girlfriend shortly after Rocco’s birth, and they got married in a super-secret Christmastime ceremony at a castle in Scotland.
“We wanted to find a place that was really hard to get to, because when people have to work hard to get somewhere, you know they really want to be there,” Madonna said of the location. Gwyneth Paltrow and Donatella Versace were among the guests.
The couple adopted a son, David, from Malawi in 2006, but just a few months later, reports surfaced that the couple’s relationship was on the rocks. There were rumours that Madonna had conducted an emotional affair with baseball player (and future J.Lo fiancé) Alex Rodriguez.
Insiders told reporters that the couple had simply been drifting apart for a while. “It wasn’t just one thing,” a source told People. “It was unravelling throughout the last year. They were living separate lives and coming together every now and then for the cameras.”
“She was more about being a celebrity and he was more low-key. He wanted to live in London and live a normal life but that’s impossible when you’re married to Madonna.”
At first, the couple’s split was amicable. In 2011, Ritchie told Details magazine: “The experience was ultimately very positive. “I love the kids that came out of it, and I could see no other route to take.”
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But in 2015 the couple entered into a bitter custody battle for their son Rocco. At first, the 15-year-old was travelling with his mum on the Rebel Hearts tour, before choosing instead to live full-time with his dad in the UK.
A judge ordered Rocco to return to Madonna’s home in NYC, but he refused. Eventually, the couple settled the dispute.
The same year, Madonna spoke a candidly about her ex-husband. “I did sometimes find myself in a state of conflict,” she told the Sun. “There were times when I wanted to express myself as an artist in ways that I don’t think my ex-husband was comfortable with.”
She added, “There were times I felt incarcerated. I wasn’t really allowed to be myself.”
In 2022, during a Q&A on YouTube, Madonna was asked if she’d ever made any decisions that she now feels wasn’t the best idea, the star kept it simple: “Getting married,” she said. “Both times.”
Guy Ritchie is now married to model Jacqui Ainsley; the couple have three kids.