Inside Michael Jackson and Madonna’s Failed Romance: From Oscar Night to a Kiss, and the Request That Ended It All

Throughout her groundbreaking career, Madonna – who recently made headlines for becoming the first female artist to score a top 10 album in every decade since the 1980s with Finally Enough Love – has always been considered the Queen of Pop. It was therefore inevitable she’d have crossed paths with the King of Pop at some point.

As two of the greatest entertainers of all time, Madonna and Michael Jackson did share a friendship. But what was the pop royals’ relationship really like?

They shared a manager who introduced them to each other

Michael Jackson first met Madonna when they were both in their early 20s and had the same manager. Photo: @drownedmadonna/Facebook

Madonna and Jackson met in the 1980s at the height of Jackson’s fame as a solo artist, when Madonna’s stardom was steadily rising. The pop music monarchs, who were coincidentally both born in August 1958, also shared a manager.

In a 2009 Rolling Stone interview, Madonna recounted how she was introduced to the “Billie Jean” singer: “I met him in the 80s, when I first started working with my manager, Freddy DeMann, who at the time was managing Michael Jackson. I saw him play at Madison Square Garden and I was blown away. He was flawless. There was a party at the Helmsley Palace Hotel. He was very shy, but it was a thrill for me.”

In fact, Madonna revered Jackson so much she even confessed to working with DeMann just because he managed Jackson: “I thought ‘Who’s the most successful person in the music industry and who’s his manager? I want him.’”

They went on the “best date ever”

 

Michael Jackson and Madonna got fans excited when they went to the Oscars together in 1991. Photo: Getty Images 

Though the superstars met in the 1980s and maintained a friendship for years afterwards, it wasn’t until 1991 when rumours started circulating about the nature of the famous pair’s relationship.

The media frenzy was sparked when the King and Queen of Pop, both wearing white, attended the 63rd Academy Awards ceremony together.

In a VH1 interview, the “Material Girl” singer detailed how that came to be: “Michael was like, ‘Well, who are you going to go with? I looked at him and said, ‘I don’t know. You want to go?’ And he said, ‘Yeah, that’d be great.’”

Madonna admitted to kissing Michael Jackson on James Corden’s Carpool Karaoke segment. Photo: Getty Images