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Wolinski, who had kissed Madonna on the cheek.
Then in December 1987, having concluded that the mercurial Sean was a liability, she filed for divorce and, while estranged from him, had a three-month dalliance with John F. Kennedy Jr, though her efforts to meet John-John’s mother, the elegantly glacial Jackie Onassis, were rebuffed. “The mother hates me,” she told friend Niki Haris.
The affair soon cooled and she returned to Sean, but by the end of the year, he had reached a point of psychological crisis. On December 29, he allegedly held Madonna prisoner in their Malibu home. Some claim he pinned her down and sat on her for hours. Madonna apparently called the police but didn’t press charges, although she did once again file for divorce and this time her decision was final. Madonna didn’t refer to the incident until 2015, when she said Sean had never struck or physically abused her.
Soon after, Madonna accepted an invitation from 52-year-old Hollywood lothario Warren Beatty to discuss a part in his new film version of DickTracy.
The complete opposite of Sean, Warren was poised, subtle and assured. He was an old-school movie actor, as smooth and perfumed as the air in Hollywood Hills. And he was delighted that Madonna was interested in him.
However, 1991’s candid documentary InBedwith
Madonna, filmed in the dying days of their affair, couldn’t disguise the fact that Warren was growing tired of his younger lover. He didn’t appreciate her crude roadielike humour and the way she bossed him around.
Madonna’s risqué 1992 coffee-table book Sex featured shots taken with another famous boyfriend, the rapper Vanilla Ice, who complained afterwards that he had no idea the pictures would end up being published. After the book came out, he refused to speak to her.
Her affair with crossdressing basketball player Dennis Rodman became one of her biggest regrets. At first, she appreciated his flamboyant style. According to Dennis, Madonna hounded him for several months, viewing him as a perfect physical specimen, and a potential husband and father, but she was hurt when he gossiped about her in his book.
By then in her mid-30s, Madonna was anxious to have children. It was in the summer of 1994 that she met a more promising partner, CubanAmerican fitness trainer Carlos Leon. She’d noticed him jogging in Central Park and arranged an introduction via her assistant. The affair grew slowly, away from the limelight. She enjoyed meeting his parents, a hardworking couple living in a modest apartment. For a while, she could make-believe this was just a normal relationship.
But Carlos had a hint of Latin machismo. It’s claimed she found him possessive and jealous, and he didn’t relish playing second fiddle to Madonna the star. While filming Evita, she discovered she was pregnant with his baby Lourdes, born on October 14, 1996. Soon after the birth,
their relationship foundered, fuelling rumours – hotly denied by Madonna – that he’d been a mere sperm donor.
Then, just a few months after the release of her triumphant 1998 album Ray
ofLight, Madonna met Guy Ritchie at a party at Sting’s lake house in England. In Guy, she found someone very like herself – driven, determined and, as a laddish film director with a privileged upbringing, adept at reinvention. He seemed like the perfect partner.
Guy was still seeing model Tania Strecker and would meet Madonna in secret, sharing passionate trysts in a tiny flat in Soho. By the beginning of 2000, she found herself pregnant with son Rocco. They married at Skibo Castle in Scotland at the end of that year and for a time, it seemed like Madonna had finally met her true match.
But in spite of Rocco and their adopted son David, the relationship gradually unravelled. Madonna was “needy”, Guy wasn’t interested in Kabbalah and he was critical of her, reportedly saying that on stage she “looked like a granny” compared to her nubile backing dancers. The divorce battle, which
concluded in November 2008, was brutal but short.
Since then, no man has come close to equal billing with Madonna. The years since have brought her well-publicised relationships with a string of hunky toyboys, three more adopted children, all from Malawi, a fight with Guy over the custody of Rocco and most recently a move to Lisbon, away from the media spotlight.
A speech she gave at the Billboard Women in Music event in 2016 focused on her 35 years of struggles in a business rife with sexism and misogyny.
It’s true she has been a flawed, kind-of-feminist icon – at different times a sexual vamp, lady of the manor, Kabbalah crusader and female shaman. But what is clear is that she has played men at their own game and more often than not, she has won with ease.