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Michael Jackson and Madonna 1991

In 1991, pop royalty Madonna and Michael Jackson made headlines for showing up to the Oscars together. Madonna had been asked to perform the Oscar-nominated song “Sooner or Later,” written by Stephen Sondheim for the film Dick Tracy, and she invited the King of Pop as her date.

Madonna explained: “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.'”