Time passes, but people still remember the moment Michael Jackson and Madonna appeared together as beautiful as a “fairy couple” 32 years ago.
“The Sexiest First Date in Oscar History”
Michael Jackson and Madonna are two legendary names in the world of music. If Michael Jackson is the King of Pop, Madonna is no less with the title of Queen given by fans.

And of course, their life is also a song of ups and downs with joy, anger, love, hate, happiness, pain and separation.

More specifically, when these two names appeared together in a moment that became a Hollywood legend many years ago.

On March 25, 1991, exactly 32 years ago, Michael Jackson and Madonna appeared together at the 63rd Academy Awards. People called this snapshot “Queen and King of Pop”.

“There have been many iconic Oscar moments over the years, but if we were to pick the sexiest first date in Oscar history, it would have to be Michael Jackson and Madonna” – that’s what the Hollywood media had to say about this special moment.

Madonna appeared at the event wearing an outfit that paid homage to Marylin Monroe, wearing $20 million worth of jewelry as she held Michael Jackson’s gloved hand.

Madonna later spoke of their special appearance: “Michael asked, ‘Who are you going with?’ I looked at him and said, ‘I don’t know. Do you want to come with me?’ He said yes and said it would be great.”

In 2018, Madonna reposted a photo of herself with Michael Jackson on her personal page, calling it “the best date ever.” A week later, the couple was spotted on a date in Beverly Hills, but that was the last time they were seen together.

The love affair just started and quickly ended.
Many years later, people are curious whether Michael Jackson and Madonna were ever together. One of the two people involved has passed away and the other rarely talks about their short time together. The rare time Madonna opened up about their relationship was probably on the show Carpool Karaoke.

Madonna said that she was the one who initiated the relationship with Michael Jackson.

Madonna paid tribute to Michael shortly after his death at the 2009 Video Music Awards: “I can’t say we were great friends, but in 1991, I decided I wanted to get to know him better. I invited him to dinner, I said ‘Hi, I’ll drive – just you and me’.”

“He agreed and came to my house without any bodyguards. We drove to the restaurant. It was dark but he was still wearing sunglasses. I said: ‘Michael, I feel like I’m talking to a limousine, do you think you could take your sunglasses off so I can see your eyes? Then he threw the sunglasses out the window, looked at me with a wink and a smile and said: ‘Can you see me now? Is everything better?’. In that moment, I could see both his vulnerability and his charm,” Madonna shared about their date.

Legendary moments of Hollywood in the 90s: The short-lived love affair of the “king and queen” of the entertainment industry – Photo 4.
“Then 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, he reached over and grabbed my hand. It seemed like he was looking for a friend more than a romantic interest, and I was glad I could help. At that point, he didn’t feel like a superstar. He felt like a human being. We hung out a few more times, and then for one reason or another, we lost touch,” the budding romance between the two ended just like that.

Madonna admitted that she was devastated and heartbroken when she heard the news of her close friend’s passing on a sad day in London: ” I felt his pain, I know what it’s like to walk down the street and feel like the whole world has turned its back on you. When I first heard the news of Michael’s death, I was in London, a few days before the start of my tour. Michael was going to perform at the same venue as me a week later. All I could think at that moment was: I’ve left him behind.”