Madonna's wild love life: Stalking models to dating Tupac and Dennis Rodman, Queen of Pop's craziest affairs

Known for her wild antics, it seems like nothing Madonna ever does is dull. But when it comes to romance, the singer enjoys taking things to a whole new level

                            Madonna's wild love life: Stalking models to dating Tupac and Dennis Rodman, Queen of Pop's craziest affairs
Tupac, Madonna and Dennis Rodman (Getty Images)

Madonna celebrates her 62nd birthday on August 16, and as we all come together to celebrate one of the most iconic pop stars of the modern era, we also find ourselves remembering what a wild ride it's been with her thus far. After all, the singer's outspokenness and brazen attitude are as much a claim to fame for her as her music and immaculate performances are. But even beyond her artistry and opinions, the singer's romantic life has been fodder for all her decades in the music industry, owing largely to the various rumors and allegations that seem to go along with every partner the singer has ever had. These stories have become such an important part of the persona that is Madonna, shaping perceptions of her and what she represents over time.

Here are five of the wildest stories about Madonna's relationships that have ever been told.

Recording artist Madonna performs a tribute to Prince onstage during the 2016 Billboard Music Awards at T-Mobile Arena on May 22, 2016, in Las Vegas, Nevada (Getty Images)

Sean Penn

Penn and Madonna married on the singer's birthday in 1985. While together, Madonna would release her third album, 'True Blue', dedicated to her husband. To the world, the duo seemed like a match made in heaven. So when rumors began floating of potential domestic abuse and infidelity, it crushed the hearts of many fans. After initially filing for an annulment in 1987, Madonna filed for a divorce in 1989 citing irreconcilable differences. But the most shocking rumors about the duo's split claimed that Penn allegedly tied Madonna to a chair and beat her up with a baseball bat in 1988. While reports varied with regards to details about the incident, they all had the common thread of alleging Penn had abused Madonna in a horrific fashion and used a 1989 complaint Madonna filed against Penn accusing him of assault as their proof, despite Madonna withdrawing her complaint a week later.

The duo rarely addressed rumors, and perhaps that helped keep the fuel going since it continued to be treated as truth until a few years ago when Penn sued 'Empire' co-creator Lee Daniels for defamation after he brought the story up again. Madonna lent her ex-husband and good friend a hand by providing a statement that denied all the allegations and added, "I am also aware of allegations concerning an incident that occurred in December 1989, which purportedly resulted in Sean’s arrest for domestic assault and battery against me. I know those allegations to be false. While we certainly had more than one heated argument during our marriage, Sean has never struck me, ‘tied me up’ or physically assaulted me, and any report to the contrary is completely outrageous, malicious, reckless and false."

David Banda, Mercy James, musician Madonna, and actor Sean Penn arrive at the 5th Annual Sean Penn & Friends HELP HAITI HOME Gala benefiting J/P Haitian Relief Organization at Montage Hotel on January 9, 2016, in Beverly Hills, California (Getty Images)

Amanda Cazalet

Madonna's devil-may-care attitude was one of the most notable things about her. Even during a time when queer relationships were rarely practiced openly, the singer was boldly going where few famous women had gone before, openly dating other women and discussing her relationships on record. While it was hardly surprising to anyone that Madonna, a celebrity famous for her wild antics and relationships, would have experimented outside of the heteronormative standards, the star's openness about her bisexuality was nonetheless extremely unconventional and led many to see her as a significant representation for an often overlooked segment of the LGBTQIA+ community. But the accounts of women she dated might make many reconsider whether they want to claim Madonna as a gay icon.

Madonna, on the hunt for models to feature in her 'Justify My Love' music video, first spotted Cazalet when she was walking down the runway for fashion designer Jean-Paul Gaultier in Paris in 1990. While filming the video and despite it not being "part of the job description," as Cazalet shared in an interview with The Sun, "Madonna suddenly put her tongue in my mouth." The video itself caused quite the stir in its time and was banned for depicting sadomasochism and bisexuality. For Cazalet, however, it depicted the moment she "was taken advantage of by someone who, at the time, was my boss." But it didn't end there for Cazalet who claims that Madonna went on to stalk her for two years. In a 1991 note that Madonna had hand-delivered to the model, she asked, "Amanda, How are you? Where are you? Why don’t you call me . . . ? Getting in touch with you is like trying to seduce the Pope!" It further read, "I’m dying to kiss you again. I fantasize about you all the time."

Despite Cazalet never responding to her many faxes, Madonna allegedly pursued her until the two met at the cinema and Madonna realized, once and for all, that the model was never going to return her affections, and they parted ways, never to meet again.


Tupac Shakur

Shakur and Madonna met at the 1993 Soul Train Awards and dated for a short while. The pair were often described as one of the most unconventional couples of their time, and it's not hard to see why. The two were seemingly worlds apart, at least where their music and artistry were concerned. Yet, their relationship rarely attracted any drama. As Shakur's brother Mopreme once told Vlad TV, "They respected each other, so it ended cool. He never talked s**t about her, not to me. And she never talked s**t about him."

But interest in their relationship was renewed when, in 2017, a letter Shakur wrote to Madonna while he was imprisoned in 1995 made its way to an auction and revealed the real reason for their split: her skin color. In his letter, the rapper stated, "For you to be seen with a black man wouldn't in any way jeopardize your career. If anything it would make you seem that much more open & exciting. But for me at least in my previous perception 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."

The letter further points to Shakur being hurt by an alleged comment Madonna made about going "off to rehabilitate all the rappers & basketball players," with Shakur stating, "Those words cut me deep seeing how I had never known you to be with any rappers besides myself." But, as it turned out, the singer actually was dating other rappers and basketball players at the time, with one, in particular, going on to tell a rather odd story about her.

Raquel Welch, Madonna, and Tupac Shakur at the Interview Magazine party in March 1, 1994, in New York City (Getty Images)

Dennis Rodman

Rodman and Madonna share one very important thing in common: both have controversial careers plagued with equally controversial alleged romances. Their fling lasted only about two months in 1994 and would have been forgotten if it weren't for Rodman making an extremely odd allegation: that the singer offered him $20 million to impregnate her.

In an interview with The Breakfast Club, Rodman stated, "She said, ‘Dennis, you know that I’m ovulating.' I said, ‘What is that?’ I was trying to f**k with her, you know? I said, 'I'll be there in five hours'." Rodman, who was at Las Vegas gambling that night, flew to New York City in a private jet arranged for him by Madonna herself, spent the night with her, and then flew back to finish gambling. In his book 'Bad As I Wanna Be' Rodman further stated, "She wanted to get pregnant really bad. She would send me faxes that said, ‘I really want to be with you, I miss you."

Rodman also claimed in the same interview that he made Madonna a star, stating that her career was on the decline while his was on the rise, and she chose to date him to help build her stardom back up again. In 1993, Madonna had starred in a string of movies that were panned by critics, was despised by audiences for rubbing the Puerto Rican flag between her legs during her 'The Girlie Show World Tour', and labeled a sexual renegade following her appearance on the 'Late Show with David Letterman' where she was censored for profanity and asking the host to smell a pair of panties she brought with her. Decades later she would reveal this appearance was during her relationship with Shakur who got her "riled up about life."

Dennis Rodman attends Sapphire Gentlemen's Club Debuts New Times Square Location on August 15, 2019, in New York City (Getty Images)

Jenny Shimizu

Madonna is largely known now for dating men that seem to get increasingly younger with each new fling. Her current beau, Kevin Sampaio, is 30 years her junior. Back when she was dating folks with a shorter age gap, though, Madonna allegedly enjoyed a brief fling with model and actress Shimizu who was nine years her junior. The relationship remained largely unknown to many, that is until Shimizu opened up about it in 2007. And her account seems to share some similarities with both Cazalet and Rodman's stories. Shimizu, who was dating both Madonna and Angelina Jolie in 1996, described being the pop icon's 'sex slave' adding that Madonna flew her to destinations around the world whenever she wanted to sleep with her. While Madonna has not confirmed or denied the allegation, it does mark the second time someone claimed she flew them over in a private jet for a clandestine affair.

Model Jenny Shimizu arrives at the Power Premiere Awards, honoring 10 Amazing Gay Women in Hollywood, at the Beverly Hills Hotel on November 11, 2007, in Beverly Hills, California (Getty Images)
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