Inside Michael Jackson and Madonna’s failed relationship: the King and Queen of Pop went to the Oscars together and kissed, but their bond took a turn after she told him to dress ‘like a girl’
- The world got excited when Madonna and MJ went to the Oscars together in white – the Material Girl even told James Corden that the pair kissed
- However, despite sharing the same manager in Freddy DeMann and dating for a while, Jackson would go on to call Madonna a ‘nasty witch’ and ‘not a nice person’
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
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”
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.’”
Years later Madonna shared on Instagram a snapshot of the night, captioned: “Best Date Ever!!”