In 1991, fans were worked into a frenzy when Madonna brought Michael Jackson as her date to the Academy Awards. In truth, the two music superstars had been attracted to each other from the first time they met in the 80's, and started hanging out semi-regularly whilst contemplating a music collaboration.

Madonna looked back fondly on her Oscars date with Jackson, Instagramming a photo from the night with the caption "Best DateEver." In 2016, Madonna talked more about her relationship with Jackson, telling James Corden that she and Michael engaged in "tongue-in-mouth kissing" — which sure sounds like commitment.

After the Oscars, the duo contemplated whether to make their relationship official, but they disagreed on a few major points. "[I]f they were going to start dating, [Madonna] wasn't going to Disneyland, [Michael's] favorite place," Flo Anthony, a friend of Jackson's, told the Outline, and Jackson's reasoning gets more serious from there.

Jackson said Madonna "is not a nice person" in the book "The Michael Jackson Tapes: A Tragic Icon Reveals His Soul in Intimate Conversation." He recalled Madonna being bossy when it came to couples' activities and being rude to a young fan in public — "don't you ever talk to children like this," Jackson recalled saying.

Although their relationship ended on terse terms, Madonna defended Jackson after his death in 2009. "He didn't seem to have any close friends. And in the last decade, everybody abandoned him, or wrote him off as crazy," she told Rolling Stone, adding that she believes "people are innocent until proven guilty."