It all started at the 63rd Academy Awards Ceremony in 1991. Madonna had been invited to perform the Oscar-nominated song “Sooner or Later” from her film “Dick Tracy”
Upon arriving at the ceremony on March 25, 1991, Madonna pulled of one of the craziest moments in her career, bringing Michael Jackson as her date!
Then, chaos ensued! At the time, they were the two biggest pop stars on the planet, and most would agree they remain so to this day.
But Madonna made the most of it and performed a Marilyn Monroed-out campy rendition of “Sooner or Later.” Also, the song did take home the Oscar!
The two even attended an after-party at Spago.
A week later, on April 9, the two were photographed together on another “date.” This time they had dinner at The Ivy Restaurant in Beverly Hills.
According to People magazine, the dates had been arranged by Madonna as a way to draw publicity to her upcoming documentary “Truth or Dare”...
And also to fuel rumors of a duet they were to perform on Michael’s upcoming album “Dangerous” (sadly, that never came to fruition).
The two drove off into the Los Angeles evening never to be seen on a date again.
People magazine pretty much summed it up on their cover: