The Madonna-Michael Jackson Relationship

Did the two biggest pop icons of the ‘80s ever get together? Let’s find out.

Brad Pitt and Angelina Jolie. Tom Brady and Gisele Bundchen. David & Victoria Beckham. We are obsessed with celebrity power couples. But no celebrity couple, past or present, could ever live up to the potential of the Madonna-Michael Jackson almost relationship.

The two were undisputed celeb royalty, influencing everything from ‘80s fashion to the entire pop music landscape. The pair would have been even more powerful if they had joined forces…which they did, briefly, until it fizzled out. 

So why didn’t music’s biggest potential power couple make it? Let’s take a look at Madonna and Michael Jackson’s (very) short relationship.

RELATED: Former maid claims Michael Jackson ‘faked’ sex with Lisa Marie Presley

Madonna & MJ: A Match Made In Music Heaven?

Michael Jackson was at the height of his career in the 1980s. He was already a household name, thanks to his stint as a member of the Jackson 5. But his best-selling 1982 album Thriller – which spawned now-classics such as “Beat It”, “Billie Jean”, and of course, “Thriller” – cemented him as one of pop music’s dominant forces.

Michael Jackson performing at a concert in 1986
(Credit: KMazur via Getty Images)

The same year Thriller came out, Madonna was pretty much a nobody. That is, until her first two singles came out in October, making her an instant club hit. But it was her second studio album, 1984’s Like A Virgin, that finally made her internationally famous. Because of her eclectic style, provocative videos, and catchy beats, Madonna became a music and fashion icon, a status she still holds to this day.

When Did Madonna And Michael Jackson Meet?

Madonna grew up listening to the Jackson 5, so how did she end up meeting her musical idol years later? The pair met in the early ‘80s thanks to Madonna’s manager at the time, Freddy DeMann. DeMann was also Jackson’s manager, and he connected the two at a party after one of Jackson’s “flawless” performances in Madison Square Garden.

What Happened At The 1991 Oscars?

Although they had maintained a professional friendship over the years, Madonna and MJ didn’t make their first public appearance together until the 63rd Academy Awards in 1991. When the two stepped out on the red carpet together – with Madonna all dressed up ala Marilyn Monroe – the media went wild

Madonna and Michael Jackson at the 63rd Annual Academy Awards After Party
(Credit: Ron Galella via Getty Images)

Just last year, Madonna posted a throwback photo of her and Jackson smiling for the cameras. She fondly referred to it as the “best date ever”. A week later, the couple was spotted out on another date in Beverly Hills, but that would be the last time anyone saw them together.


Did Madonna And Michael Jackson Ever Kiss?

Madonna has kept quiet about the dirty details of her relationship with Michael Jackson…until recently, when she spilled the deets on an episode of Carpool Karaoke with James Corden. Apparently, the couple did share an intimate kiss, and with tongue too. Madonna admits she made the first move, and that she “loosened” Michael up a bit with a glass of Chardonnay, after which he was a “willing accomplice.”

Why Did Michael Jackson & Madonna Never Get Together?

There’s a lot of speculation about why the King and Queen of Pop didn’t work out. One source, a family friend of Jackson’s, said that it was over when Madonna criticised the Thriller singer’s sense of style. 

According to Flo Anthony, Jackson was furious that Madonna ragged on his “buckles” on national TV. She also allegedly spent the night at Neverland and refused to ever go to Disneyland – Jackson’s favourite place in the world. This was a major deal-breaker for Michael.

A black and white photo of Michael Jackson & Madonna
(Credit: Galella, Ltd./Ron Galella Collection via Getty Images)

Mark Lester, another old friend of Michael’s, gave an alternative explanation. Lester, who is rumoured to be the sperm donor/biological father of Jackson’s two kids (Paris and Prince), said that the sight of Madonna naked turned Michael “gay”. 

Jackson entered the bedroom, and Madonna was sprawled across the bed. She saw Jackson, threw off the blankets, and was fully nude. Jackson saw her, screamed loudly, and ran immediately from the room,Lester revealed to The Daily Mail.

What Does Madonna Think About The Recent Allegations Against Michael Jackson?

Allegations of sexual abuse against Michael Jackson are by no means a recent thing. The earliest accusations of pedophilia surfaced in the early ‘90s, but the case was settled out of court. A second allegation came out in the early aughts, shortly after it was revealed that Jackson saw nothing wrong with having sleepovers with minors, often in the same bed.

But things really came to a head very recently. Earlier this year, a documentary titled Leaving Neverland was released. The documentary follows two men who allege that Jackson abused them when they were kids.

Michael Jackson sitting with 10 year old Jimmy Safechuck on his tour plane
(Credit: Dave Hogan via Getty Images)

Madonna came out to defend her former friend. She admitted in May that she hasn’t watched the documentary but has plans to. She then said that people are innocent until proven guilty. She drew flak for her statement, forcing her to retract her statement and apologise publicly.


Although Madonna and Michael Jackson didn’t date for very long, their individual legacies and contributions to music will stand the test of time. Unfortunately, Jackson’s legacy is forever tainted by the child sexual abuse allegations, which his former friends (like Madonna) are left to grapple with today.

RELATED: Madonna: Why my kids ended their relationship with me

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