Top 18 Ex-Boy Toys of Madonna

    Looking back…Reflecting on Madonna’s past declarations of love inspiring generations with new music.

    Well it is no secret that Madonna’s love-life has been the topic of conversation for decades on end as her list of suitors reads like a time capsule artifact of who was hot and happening in Hollywood. Of course there are a few unrecognizable names by the general public’s standard, but these men, and lady,  are still no “Average Joe’s”. Athletes, Actors, Musicians, Producers, Dancers, etc… the world renowned pop-star has surprised her fan base with a revolving door of past lovers who simply could not resist her powerful charms.

    No one was safe!

    Madonna is known for being an equal opportunist when it came to her sexual escapades, and the critically acclaimed, infamous documentary, Truth or Dare chronicled her free spirit attitude solidifying Madonna as the ultimate provocateur even late into her 50s.

    Madonna is the epitome of someone who identifies “age being just a number” and “everyone is fair game”.

    #18  Timor Steffans


    Her current boy toy is no stranger to the extravagant life as he vacations in Cannes with the entire family. This choreographer is the most current headline attached to Madge!


    #17 Brahim Zaibat

    September 2010- December 2014

    This beau of the moment lasted longer than most people anticipated. However, the dancer turned significant other is just another example that if you have balls enough to put the moves on Madonna, you may just be able to dance your way into the limelight and her heart.


    #16 Jesus Luz  

    Late 2008- Early 2010

    Brazilian model, Jesus, connected with the reigning queen of pop over their shared passion for the Kabbalah faith.


    #15 Alex Rodriguez


    The New York Yankee has always been linked to a bevy of beauties and A-listers, but the rumor mill was spinning out of control when the accusations began while he was still married to then wife. He filed for divorce shortly after the word got out, however, neither ever admitted to any wrong doing.


    #14 Guy Ritchie

    Husband from 2000-2008

    So this dates back to a time where Madonna turned full Brit. They seemed like the perfect English family as she became more demure and poised throughout their 8 year marriage.

    US singer Madonna (L) and her husband Br


    #13 Carlos Leon


    Father to their only daughter, Lourdes, Carlos was a personal trainer when they first stepped out on the scene together. Unfortunately, their relationship fizzled shortly after their little heiress’s birth.


    #12 Dennis Rodman 


    Does this shock anyone? The only aspect about this collaboration that turned heads was how short of an affair it turned out to be.

    #11 Jenny Shimizu 


    Jenny is well-known for her brief romance with the flawless Angeline Jolie, but she has also confirmed to have been double dipping. Jenny admits to wooing Madonna and Angelina at the same time. You go girl!

    2010 RxART Party


    #10 Tupac


    As we know Howard Stern can get anyone to own up to all their dirty laundry. This includes the revelation of an unknwn relationship between her and Tupac.


    #9 Vanilla Ice


    I guess this made sense at the time. However, most people have forgotten all about this brief moment in history where this was the coolest thing that could have happened in music. Think Gomez and Beiber.


    #8 Jose Canseco 


    This fling didn’t go the whole nine yards because they could not agree on their future together, oh and possibly because he was still trying to work things out with then wife while Madonna relentlessly attempted to seduce him, or so he claims.


    #7 Tony Ward


    I mean, who is this guy…Next.


    #6 Lenny Kravitz 


    After “Justify My Love” was released, speculation arose fast, even though Lenny Kravitz was famously known for being married to Lisa Bonet. Lisa used the allegations to justify her divorce. Irony at it’s finest.

    1998 MTV Video Music Awards



    #5 Warren Beatty 


    Madonna and Warren Beatty had  a legendary affair for the ages as the womanizer inspired her hit “Vogue.” Madge remains to express, “Warren was the most incredible lover I have ever had!”


    #4 John F. Kennedy Jr. 


    This one makes me jealous as John F. Kennedy Jr. is the poster of America royalty and quite possibly the most handsome heartthrob to ever grace magazines. The Daily Mail reports that John F. Kennedy Jr. and Madonna had a steamy affair in 1988 after her marriage with Sean Penn was doomed, but not officially (or legally) over. What made it even more torrid? Jackie O. reportedly detested Madge because she posed as Marilyn Monroe, who is widely rumored to have had her way with JFK.

    #3 Sean Penn 

    Husband 1985-1989

    Madonna and Sean Penn had one of the most tumultuous relationships in Hollywood history. The pair met in February 1985 and married that August proving fools really do rush in. Penn’s temper flared often, both against the paparazzi and against Madonna herself: The Daily Mail reports Penn attacked Madonna with a baseball bat in 1987, sending her to the hospital for X-rays. She filed for divorce shortly after before reconciling with the troubled Oscar winner. It wouldn’t last: In 1989, Penn is said to have kidnapped Madonna, tying her to a chair and abusing her for over nine hours. They finally divorced that year.



    #2 John “Jelly Bean” Benitez


    The DJ, producer, and mixer was the “IT” boy of the Manhattan social circuit in the early to mid 80s.

    #1 Jean-Michel Basquiat


    Apparently when late artist Jean-Michel Basquiat broke up with someone, he broke up with them hard, because according to Madonna, their relationship ended with the artist taking back canvases he’d given her and painting them over with black. Madonna confided to Howard Stern about her relationship with Basquiat recently, saying that she loved him, but he was addicted to heroin, which was ultimately the cause of death for this fallen angel at 27 years old. She also mentioned that his work ethic and artistry was a huge influence on her life and in her music:

    “I remember getting up in the middle of the night and he wouldn’t be in bed lying next to me; he’d be standing, painting, at four in the morning, this close to the canvas, in a trance. I was blown away by that, that he worked when he felt moved.”



    And there you have it, a look back on Madonna’s historic “little black book” ! To be continued…


    • Tom La Vecchia

      Founder of New Theory & X Factor Media

      Founder and Publisher of New Theory Magazine and Podcast. Serial Entrepreneur who loves wine, cigars and anything that allows to people to connect and share experiences.

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