There have been many iconic Oscars moments over the years, but if we’re picking what must have been the most glamorous first date in Academy Awards history, it has to be Michael Jackson and Madonna.

By 1991, Michael Jackson and Madonna were the world’s two biggest popstars. The King of Pop and the Queen of Pop.

That year’s Oscars took place at the Shrine Auditorium in Los Angeles, with awards going to films including Misery, Goodfellas and Ghost.

But before the event had begun, all eyes were on the red carpet. If this was the era of social media, one couple’s arrival would have ‘broken the internet’.

Madonna was in attendance to perform her soon-to-be Oscar-winning song ‘Sooner or Later’ from the Dick Tracy soundtrack.

She turned up the glitz and glamour to the max by turning up with none other than Michael Jackson.

Madonna and Michael Jackson in 1991. Picture: Getty
Madonna was dressed in homage to Marylin Monroe, wearing jewellery worth a reported $20 million, while holding Michael Jackson’s gloved hand. It wasn’t long before rumours of an unexpected romance had begun.

Speaking about the date later on, Madonna explained how it all came about.

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

Decades later, while appearing on Carpool Karaoke, Madonna spoke more about the date with host James Corden, revealing how close they had got that night.

“I mean, baby, I’ve been around,” she joked, saying that a glass of chardonnay helped the King of Pop to “loosen up,” transforming him into a “willing accomplice” and leading to “tongue and mouth kissing.”

Writing on Instagram, Madonna also looked back on the night, describing it as the “Best Date Ever!”

Madonna and Michael Jackson remained good friends until the King of Pop’s passing in 2009.

The ‘Material Girl’ singer paid an emotional tribute to Michael soon after his death at the 2009 Video Music Awards.

She referenced another night out with the star during the speech, saying: “I can’t say we were great friends, but in 1991 I decided I wanted to try to get to know him better. I asked him out to dinner, I said ‘My treat, I’ll drive — just you and me.’

Michael Jackson and Madonna went out a few times. Picture: Getty
“He agreed and showed up to my house without any bodyguards. We drove to the restaurant in my car. It was dark out, but he was still wearing sunglasses. I said, ‘Michael, I feel like I’m talking to a limousine. Do you think you can take off your glasses so I can see your eyes?’

“Then he tossed the glasses out the window, looked at me with a wink and a smile and said, ‘Can you see me now? Is that better?’. In that moment, I could see both his vulnerability and his charm.

“The rest of the dinner, I was hellbent on getting him to eat French fries, drink wine, have dessert and say bad words. Things he never seemed to allow himself to do. Later we went back to my house to watch a movie and sat on the couch like two kids, and somewhere in the middle of the movie, his hand snuck over and held mine.

“It felt like he was looking for more of a friend than a romance, and I was happy to oblige. In that moment, he didn’t feel like a superstar. He felt like a human being.

“We went out a few more times together, and then for one reason or another we fell out of touch. Then the witch hunt began, and it seemed like one negative story after another was coming out about Michael. I felt his pain, I know what it’s like to walk down the street and feel like the whole world is turned against you.

“When I first heard that Michael had died, I was in London, days away from the start of my tour. Michael was going to perform in the same venue as me a week later. All I could think about in this moment was, ‘I had abandoned him.’ That we had abandoned him. That we had allowed this magnificent creature who had once set the world on fire to somehow slip through the cracks.

“While he was trying to build a family and rebuild his career, we were all passing judgement. Most of us had turned our backs on him. In a desperate attempt to hold onto his memory, I went on the internet to watch old clips of him dancing and singing on TV and on stage and I thought, ‘my God, he was so unique, so original, so rare, and there will never be anyone like him again. He was a king.’