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The life and times of Madonna through her dating history

Posted Sun 03 Jun 2012 07:42:19 pm in News, Entertainment | By News Desk

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’d 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 seventies. 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 also immediately started work 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 has arrived. Madonna, 26 then, went from performing in New York clubs to packed arenas. She quickly followed it up with Like a Virgin in 1984, which became an even bigger success. Suddenly, fishnet stockings, bleached hair, rosaries 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, although Arquette went on to win most of the accolades . The film was a boxoffice hit.

Rubbing shoulders with the who’s who of Hollywood, Madonna met Sean Penn in 1985, and their’s became one of the 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 albums 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. In 1989, she again made an appearance in the musical Bloodhounds of Broadway (1989), which went mostly unnoticed.

Penn and Madonna divorced in 1989 amidst widely speculated claims their marriage was a violent one. Penn, two years younger than Madonna (a sign of things to come?) 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. The title song became Madonna’s seventh No1 Billboard Hot 100 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 lady’s 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 best selling compilation albums of all time, thanks also to new tracks Justify My Love and Rescue Me included in the album.

Tony Ward (1991)

Even more brief than her Beaty 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. The less said about those pictures, the better, but famously released the same time was Madonna’s 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 had over the years. But 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 tatooed 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. She was critically praised and the film was a commericial success. Despite her asking us not to cry for her, we all surely did.

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 would call it a masterpiece and credited her for introducing electro music to mainstream pop. Many, of course, would come to follow in her footsteps.

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 eight album and another certified milestone. A few months after Rocco’s birth, Madonna and Ritchie adopted Malawian child David Banda amidst much controversy.

In 2003, American Life, her ninth album, was released, followed in 2005 by the very retro Confessions on a Dance Floor. The later, 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 “I think I’d rather get run over by a train.”

The same year, Hard Candy, Madonna’s eleventh album was released. Despite some critics accusing her of pandering to the mainstream, the album was a major success, especially the single 4 Minutes, which was a duet with Justin Timberlake.

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. Although Madonna has never publicly acknowledged their relationship, the pair were seen gallivanting around the world as Luz became a constant companion. He even appeared in the video for ‘Celebration’, the single, also the name of the compilation album 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 choice.”


In March 2012, Madonna released her 12th album, MDNA to much fan fare, following up with the announcement of a world tour which included two nights in the UAE. Zaibat will be in Abu Dhabi with Madonna and her children.

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