The pop icons went to the ceremony back in 1991, after the ‘Like A Virgin’ star was nominated for her song ‘Sooner or Later’ – written by Stephen Sondheim for the film Dick Tracy. That evening, she would take home the award for Best Original Song.
Now taking to Instagram, Madonna has shared photos of the pair in attendance at the awards – marking it as ‘the best date ever’.
Speaking in an interview at the time, Madonna said: “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’. And then, yes, he took me home. You wanna know what happened after that? I’m not gonna tell you.”
She would later reveal to James Corden on Carpool Karaoke that the pair shared a kiss.
She then also shared photos of herself at the 2018 Oscars:
Madonna is currently among the rumoured headliners for Glastonbury 2019.
“He was my best friend growing up for a good, fat stretch of my life,” said Culkin.
“He enjoyed my youthfulness. He liked being a kid with me. It never struck me as odd. I never felt uncomfortable. That was just the way he was.”