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Remembering Madonna & Michael Jackson’s Short-Lived Love Affair

Did you know that Madonna and Michael Jackson used to date? Find out more about their brief love affair!
Michael Jackson performing on stage in a red jacketGetty

Nobody saw it coming when Michael Jackson and Madonna started dating back in the 90s. They were both legendary artists, performers, and pop icons in their own right – so it made sense for them to join forces, didn’t it? The unlikely pair made headlines all over the media and tabloids, but their relationship fizzled out almost as quickly as it began.

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How did they get together and why didn’t their love affair last? What does Madonna think about the late Michael Jackson’s battle with sex abuse allegations? Read on to find out more about the celebrity couple that was too good (or bad) to be true!

RELATED: How has Michael Jackson’s family reacted to ‘Leaving Neverland’?

The King & Queen Of Pop

Michael spent most of his childhood performing in The Jackson 5, but his career took off after his groundbreaking 80s hits dominated the charts. Thriller was the best-selling album that shot him to superstardom with classics like ‘Thriller’, ‘Beat It’, and ‘Billie Jean’, among many others. The King of Pop was doing a show for his Victory tour in 1984 when he first met Madonna, who was a rising star with a few singles under her belt.

Michael Jackson performing on stage in a red jacket
(Credit: Getty)
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A few years after they met, Madonna took the world by storm with her songs ‘Like A Virgin’, ‘Material Girl’, and ‘Holiday’. She captivated audiences everywhere with her edgy, sensual, and controversial performances. The ‘Lucky Star’ singer released one club-banger after the other, and not long after, the world dubbed her the Queen of Pop and the ‘Female Michael Jackson’.

Madonna performing on stage in Montreal wearing a black outfit
(Credit: Getty)

About Their Relationship

In 1991, Madonna and Michael Jackson reconnected through their shared manager Freddy DeMann. To freshen up his music, Michael reached out to discuss a collaboration with Madonna for a song on his upcoming album. Eventually, paparazzi spotted them driving together to dine at a famous restaurant called The Ivy in Beverly Hills.

A Date At The Oscars

Later on that year, the two pop icons shocked fans all over the world when they made their flashy debut together at the 63rd Academy Awards. Madonna was as glamorous as ever, covered with diamonds in a dress inspired by the sex icon Marilyn Monroe. Not to mention, she had the world’s most successful recording artist right by her side on the red carpet.

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In an interview with VH1, Madonna shared that it was a spontaneous date. Michael was like, ‘Well who are you gonna go with?’ I looked at him and said, ‘I don’t know. You wanna go?’ And he said, ‘Yeah, that’d be great. And then, yes, he took me home. You wanna know what happened after that? I’m not gonna tell you.Years later, Madonna shared a throwback photo from that night on an Instagram post captioned ‘best date ever!’

The Naked Truth

Did Michael Jackson and Madonna ever get intimate? Madonna admitted on James Corden’s Carpool Karaoke that she and MJ had kissed once, but it looks like they didn’t get any further than that.

Madonna lying naked on a bed on set of Body of Evidence
(Credit: Getty)
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Former child-star Mark Lester, who is a close friend of Michael’s, confessed to having been the sperm donor for Prince and Paris Jackson. Lester shared in an interview with the Daily Mail that Michael couldn’t handle Madonna’s sexual prowess. When he entered the room, she was in bed, threw the covers off and was completely naked. He took one look at her and screamed and ran away – not something I’d have done!

Why It Didn’t Work

There were several reasons the relationship crashed and burned. Reports claim that Madonna had backed out of their song ‘In The Closet’ when Michael didn’t go with her vision for the music video. He thought she was all about the shock factor, while he wanted to make sentimental songs.

Michael shared on several interviews that Madonna refused to go to Disneyland with him – a major deal-breaker since that was Michael’s favourite place on earth. He recalled an incident from their date at The Ivy, saying that a kid had walked up to them and Madonna rudely made him leave. MJ also mentioned she would talk badly about his style with the press. He didn’t seem to appreciate her suggestions, and his frustrations grew as she tried to influence him in different ways.

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Madonna On Michael Jackson Allegations

While Madonna has not yet seen the Netflix documentary Leaving Neverland, she remains on his side even after all the allegations. She had a touching speech for him during the 2009 MTV Video Music Awards, recalling her fond memories with the misunderstood artist. In the same year, she had a thrilling tribute for him during one of her ‘Sticky and Sweet’ tour shows.

Michael Jackson testifying while on trial
(Credit: Getty)

Despite everything that happened, Madonna defended Michael against sexual abuse allegations. She shared in an interview with Sky News: I don’t have a lynch-mob mentality, so in my mind, people are innocent until proven guilty. I’ve had a thousand accusations hurled at me that are not true. So my attitude when people tell me things about people is, ‘Can you prove it?’”

Conclusion

The two superstars shot to the top of the charts, but they couldn’t win over each other’s hearts. Being pop royalty is never easy, but finding love is even harder when you’re as famous as Michael Jackson and Madonna. Looking back is bittersweet, and it seems like Michael’s recent controversies have overshadowed his colourful dating history.

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In the end, their failed relationship didn’t take away from their popularity and success as individual artists. Though their time together was short-lived, their legendary legacies live on forever through their music!

RELATED: Michael Jackson’s Skin: Why Did Michael Jackson Turn White?

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