Remember When Madonna and Michael Jackson Went to the Oscars Together?

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When you have music stars couple-up, it becomes headline-rocking news. But when they’re the two greatest musicians of our time and their first date is a red carpet appearance at the Oscars, it becomes the stuff of legends. Such was the case when Madonna (who turns 60 today) and Michael Jackson, aka the Queen and King of Pop, showed up hand-in-hand at the 63rd Academy Awards in 1991, igniting what would become a brief—and strange—whirlwind romance.

It all began when Madonna was invited to perform the nominated hit “Sooner or Later” from the Dick Tracy soundtrack (which would win Best Original Song) during the ceremony. Finding herself without a date, she turned to her friend. “Michael was like, ‘Well who are you gonna go with?’ I looked at him and said, ‘I don’t know. You wanna go?’” Madonna reminisced. “And he said, ‘Yeah, that’d be great.’”

That night, she channeled Marilyn Monroe, slipping into a glittering Bob Mackie creation and dripping in million worth of Harry Winston diamonds, finishing both with a fur shawl, white opera gloves, and white satin shoes. Meanwhile, Jackson pulled a classic MJ look: a sequined blazer, a stunning brooch in lieu of a bowtie, an extravagant gold belt casually slung at the hips, and shiny embossed pants. After the ceremony, the two kept the night going, showing up together at Spago’s for the Oscars after-party.

“And then, yes, he took me home. You wanna know what happened after that? I’m not gonna tell you,” Madonna teased.

But in a “Carpool Karaoke” segment, the singer revealed to James Corden that they had kissed. “Tongue in the mouth kissing,” she elaborated, adding that she made the first move because he was too shy. “However, he was a willing accomplice. I did sort of get him to loosen up with a glass of chardonnay, and it worked wonders.”

A week after their Oscars appearance, Madonna and Jackson were spotted on a date at The Ivy in Beverly Hills, though it was reported that it was arranged to drum up publicity for Madonna’s forthcoming Truth or Dare documentary and to fuel rumors of a possible duet in Jackson’s album Dangerous. That was the last time they were spotted together, but it didn’t stop outlets from naming them “the oddest couple.”

As it turns out, there was drama that caused a rift between the two. Jackson’s longtime friend Flo Anthony went on the record to explain what happened: “He told me that she’d told him if they were going to start dating, she wasn’t going to Disneyland, his favorite place. The reason their relationship didn’t stick was because she did an interview on TV saying she would like him to get a new look and she wanted to get him out of those buckles. He was livid that she criticized him on TV. I’m not sure, but I don’t think he ever spoke to her again.”

Regardless of how it went down, Madonna still holds the memory close to her heart, Instagramming a throwback photo of them and captioning it “Best Date Ever.” And that was more than enough of a reason for Kim Kardashian and Kourtney Kardashian to recreate their looks for Halloween (Kim as Madonna; Kourtney as Jackson), which not only honored a major pop culture moment, but paid tribute to two legendary musicians.

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