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.
In an interview at the time, 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.'" She teased, "And then, yes, he took me home. You wanna know what happened after that? I'm not gonna tell you." (We do know they did at least kiss, at some point, thanks to her episode of Carpool Karaoke.)
Flash forward to 2018: Madonna is now looking back at that night as her "best date ever."