Madonna’s taste in men is as colourful as her career. From artists to models and from personal trainers to film directors, her dating history is as star-studded as they come. Although she’s now famously sworn off marriage, (“I think I’d rather get run over by a train”), her life and career, interestingly, is best reflected by the men she has been with. Yes, it’s true. Read on as tabloid! breaks it down for you…
Dan Gilroy (1979 -1981)
Back in the day, Madonna, like all of us, had bills to pay. So, as any aspiring musician would, she made movies. She was desperate, it seems, having been paid just $100 (most of the cast members weren’t paid) for her role of Bruno in indie film A Certain Sacrifice (1979), the story of a New York City resident who lives with three sex slaves who indulges in petty things like human sacrifices. Madonna, after she became famous, apparently tried to buy the rights of the film to stop it from being seen. She didn’t succeed.
That same year, she also joined a pop group called the Breakfast Club, her first band, which formed in the ’70s. She and lead vocalist Dan Gilroy dated a few years before she moved on and started another band called Emmy.
Jean-Michel Basquiat (1982)
Still an aspiring pop star, Madonna hounded the New York party scene and in 1982 met American graffiti artist Jean-Michel Basquiat, whom she began dating. The same year, Madonna released her first single, Everybody, which became a dance hit, and immediately started working on her first album. Her relationship with Basquiat was brief and the artist died in 1988 of a heroin overdose at his art studio.
John Benitez (1983-1985)
Whilst working on her first self-titled album, Madonna mixed work with pleasure as her relationship with musician/producer John ‘Jellybean’ Benitez quickly developed into a fully-fledged romance. Benitez worked on many of her songs in her debut album, including Everybody, Borderline, Lucky Star, and Holiday, which became major hits. Madonna, the album, released in 1983, peaked at No 8 on the Billboard 200 and turned the singer into an overnight sensation.
Sean Penn (1985-1989)
A star had arrived. Madonna, then 26, went from performing in New York clubs to packed arenas. She quickly followed it up with Like a Virgin in 1984, which became a big success. Suddenly, fishnet stockings, bleached hair and hoop earrings became the fashion must-haves and Madonna quickly capitalised on it by making a move to Hollywood. She began with a cameo in Vision Quest (1985), where she plays a bar singer, and performs the title song Crazy For You, which became a hit. The same year, she appeared in her first major role in a big production, playing Susan alongside Rosanna Arquette in the drama Desperately Seeking Susan. She received positive reviews for her supporting role.
Rubbing shoulders with the who’s who of Hollywood, Madonna met Sean Penn in 1985, and theirs became one of the industry’s most high-profile relationships. After their marriage they starred in the universally panned and box office disaster Shanghai Surprise (1986). As if to offset that disappointment, Madonna released her third album, True Blue, that year. With hits like Papa Don’t Preach and La Isla Bonita, the record-breaking album is considered one of Madonna’s most successful, along with Like A Virgin (1984) and The Immaculate Collection (1990).
The next year, Madonna fronted another comedy, Who’s That Girl (1987), also a major flop. Thankfully for her though, the soundtrack, including the title song, as we all know, became a global hit. Penn and Madonna divorced in 1989 amidst widely speculated claims their marriage was a violent one. Penn, two years younger than Madonna, later said of their marriage: “Loud. That’s how I remember it. I don’t recall having a single conversation in four years of marriage.”
Despite the well-documented divorce, that year also saw the release of Like A Prayer, another massive hit.
Warren Beatty (1990)
Despite her immense success, Madonna was still trying to come to grips with her fledgling Hollywood career. After playing a small role in Dick Tracy (1990) with Hollywood’s original ladies’ man Warren Beatty, the gig led to a brief relationship between the two. Musically though, Madonna crossed another milestone, releasing a greatest hits album, The Immaculate Collection, which is one of the bestselling compilation albums of all time, thanks to new tracks Justify My Love and Rescue Me.
Tony Ward (1991)
Even more brief than her Beatty relationship was one with the model Tony Ward, who starred in her controversial music video of Justify My Love. The same year she also reportedly dated baseball player Jose Canseco, although, for how long, it is not known. Canseco many years later claimed Madonna wanted to have a child with him, telling Fox News: “I’m Cuban and she wanted a Cuban child. She wanted to get married and have a child with me. I then told her I was trying to work things out with my wife. That if I left her I would lose a lot of money and she said, ‘I have lots of money. Don’t worry about that.’”
Vanilla Ice (1992)
The Ice Ice Baby singer and Madonna didn’t date for long but long enough for him to appear in her book, Sex. She also famously released her fifth studio album, conveniently titled Erotica. Despite all the controversy around the book and the album, musically, Madonna rode high as the album became a critical and commercial success. She also had time for some more movies, playing a small role in the Woody Allen film Shadows and Fog and starring in the hit A League of Their Own.
The next year Madonna tried to carry the sex theme over with erotic thriller Body of Evidence. Critics weren’t too kicked though, but she managed to calm some nerves with her performance in Dangerous Game.
Dennis Rodman and Carlos Leon (1994)
After a controversial few years, Madonna kicked off 1994 with the release of her sixth album, Bedtime Stories, creating in its wake a new pop star. More demure, more toned down and with an R&B twinge, this album didn’t quite measure up to the massive success the singer had over the years. Still, the songs Secret and Take a Bow ensured it stayed on top.
Yet, even while in the midst of trying to tame her image, Madonna’s love life took the usual trajectory, in the form of a cross-dressing, piercing-obsessed and tattooed NBA star. But Dennis Rodman and her didn’t last long and Madonna quickly warmed up to her personal trainer Carlos Leon. It was short but the relationship with Leon produced Lourdes, now 15. Her role in the 1995 film, Four Rooms, by Quentin Tarantino, might have been widely panned, but it was her career-defining role as Eva Peron, in the 1996 film Evita that Madonna will most want to be remembered for.
Motherhood seems to have calmed our favourite wild child. In 1998, her album Ray of Light, her seventh, took another musical direction. Mature and spiritual, many critics called it a masterpiece.
Guy Ritchie (1999-2008)
Undoubtedly Madonna’s longest and most tame relationship yet. The singer and the British director were introduced to each other at a party hosted by Sting in 1998 and got married in 2000 in Scotland. Madonna, then 42, was 10 years Ritchie’s senior. The same year, their son Rocco was born and Madonna launched Music, her eighth album. A few months after Rocco’s birth, Madonna and Ritchie adopted Malawian child David Banda.
In 2003, American Life, her ninth album, was released, followed in 2005 by the very retro Confessions on a Dance Floor. The latter, was widely acclaimed for its musical direction.
In 2008, amidst rumours that the singer was having an affair with a very married baseball player Alex Rodriguez, Ritchie and Madonna announced they were headed for a divorce. Asked later if she would ever get married again, Madonna told People.com: “I think I’d rather get run over by a train.”
Despite the box office disaster Swept Away (2002), directed by Ritchie and starring Madonna, the director seemed to have triggered directorial ambitions in the singer, who made the widely panned Filth and Wisdom. Critics urged her not to give up her day job.
The same year, Hard Candy was released. Despite some critics accusing her of pandering to the mainstream, the album was a major success
Jesus Luz (2009)
Madonna, 50 by this time, met 22-year-old Brazilian model Jesus Luz at a steamy photo shoot for W magazine in 2009. He even appeared in the video for Celebration, the single from the compilation album of the same name released this year. The relationship ended by 2010.
Brahim Zaibat (2011 to present)
At the launch of Madonna’s clothing line Material Girl, a young French dancer caught the pop star’s eye. And so it was that Brahim Zaibat would become her constant companion and love.
“I didn’t choose to, you know, I didn’t, like, write down on a piece of paper I’m now going to have a relationship with a younger man,” Madonna told ABC News. “That’s just what happened. You see, that’s the romantic in me. I just met someone that I cared for, and this happened to be his age.
“I’ve never really lived a conventional life,” she added. “So I think it’s quite foolish for me or anyone else to start thinking that I am going to start making conventional choices.”
True to form, Madonna proved she hadn’t learned from her 2008 failure, releasing her next ambitious directorial venture W.E. In March 2012, Madonna released her 12th album, MDNA, to much fanfare, following up with the announcement of a world tour which included two nights in the UAE. Zaibat will be in Abu Dhabi .