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From Guy Ritchie to Tupac and Prince, we look back at Madonna’s most significant hook-ups and husbands
MADONNA is no stranger to passionate love affairs and has wowed fans with her choice of celebrity fling.
We look back at her most significant hook-ups and husbands as the pop icon turns 60.
Jellybean Benitez, 1983-85
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Whoever said you shouldn’t mix business and pleasure?
It worked for Madge as she and Jellybean, now 60, got together around the same time he started producing her music.
Jellybean, AKA John (yeah, not quite so cool), is responsible for her first global hit Holiday, as well as Lucky Star and Borderline.
The Madonna we know and love was born.
Prince, 1985
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This unlikely pairing lasted for two months before it became apparent they wanted different things and Prince, who died two years ago aged 57, called it quits.
There’s a jaw-dropping piece of showbiz folklore about Sean Penn discovering Madonna had dated Prince and punching a hole in the wall in a fit of rage.
Rumour has it Madonna then called Prince to come over and repair the damage “because you’re responsible for it, after all”. And Prince actually did. A-mazing.
Sean Penn, 1985-89
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They hooked up while she was filming the video for Material Girl and got hitched months later on her 27th birthday.
They separated amid reports of heated arguments and she filed for divorce in 1987, but then changed her mind, only to go through with it in January 1989.
Earlier this year Sean, 57, told The Late Show: “I love my first wife very much,” while, in 2016, Madonna said she was “still in love” with him.
Madonna twerks in teaser for Carpool Karaoke with James Corden
John F Kennedy Jr, 1988
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During her marriage breakdown, Madonna enjoyed a fling with John Jr.
Once labelled the sexiest man alive by People magazine, John said of her: “She’s a sexual dynamo,” much to his mum Jackie Onassis’ disapproval, apparently due to Madonna’s use of Catholic images.
They remained friends until he died in a plane crash in 1999, aged 38.
Warren Beatty, 1989-90
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Adding to the many, many notches already on his bedpost, Warren got it on with Madge while they were filming Dick Tracy.
The actor, now 81, asked Madge to marry him, but it all fizzled out after 15 months, which coincided nicely with the release of their movie…
Warren Beatty stars as Howard Hughes in film 'Rules don't apply'
Vanilla Ice, 1991-92
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They were a couple for less than a year, but Robert Van Winkle’s (yup, really) part in Madonna’s long history of lovers has been immortalised forever in her 1992 book Sex.
Without his consent, it included massive pics of them getting hot and heavy and Rob, now 50, dumped her, saying he was an “unwitting part of this slutty package. It was disgusting and cheap”.
We’re guessing she’s off his Christmas card list then.
Vanilla Ice sings Ice Ice Baby
Tupac Shakur, 1993-94
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They met at an awards do and dated for a few months before Tupac, who was shot dead in 1996 aged 25, wrote a letter to Madonna in prison - where he was serving time for sexual assault - explaining that he dumped her because of her race: "I felt due to my 'image' I would be letting down half of the people who made me what I thought I was. I never meant to hurt you."
New US TV drama will investigate mystery behind murders of Tupac and The Notorious B.I.G.
Dennis Rodman, 1994
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The basketball star, now 57, dated Madonna at the height of his career and has since said in his autobiography Bad As I Wanna Be that she wanted kids with him.
“[She] talked all the time about having a baby. I think she wanted every bit of Dennis Rodman – marriage, kids, everything.”
Carlos Leon, 1994-97
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But Madonna did get her longed-for baby a couple of years later with dancer and fitness trainer Carlos Leon, now 52.
Lourdes Leon was born in October 1996, but the following year Madonna decided she and Carlos were better off as “best friends”.
He’s since said: “I have no regrets. I wouldn’t change anything.”
The pair have co-parented very cordially and have even been spotted working out together as well as hanging out with Lourdes.
Lourdes in Havana, Cuba with family and friends to celebrate? Madonna?'s? 58th birthday
Guy Ritchie, 1998-2008
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Madge finally met her match in 1998. During what was by far her longest relationship, she liked nothing more than donning a flat cap and having a pint with the British film director.
Guy, now 49, has been credited as being the only man who managed to tame her, and they married in December 2000 following the birth of son Rocco that August.
But by 2008, Madonna had filed for divorce, citing irreconcilable differences.
Guy has said: “She’s obsessed with her public image,” while she’s branded him “emotionally retarded”. Ouch.
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Jesus Luz, 2008-10
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Having met on a photoshoot for W magazine shortly after her divorce from Guy, Madonna and the Brazilian model’s relationship lasted a year.
Jesus, 31, has said that because of the age gap – he was just 21 and Madonna 50 when they got together – they had nothing in common.
Except Kabbalah. And the fact they could almost be the most famous of mothers and sons. The Madonna and Jesus, geddit?
Brahim Zaibat, 2010-2013
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He was a dancer for the launch of her clothing collection, and even though everyone said it wouldn’t work because of the age difference (again), Brahim, now 31, went on to be Madge’s backing dancer/lover.
They lasted three years, blaming the split on conflicting schedules.
Hopefully she’s not too Hung Up.
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