Legendary moments of Hollywood in the 90s: The short-lived love affair of the “king and queen” of the entertainment industry

As time passes, people still remember the moment Michael Jackson and Madonna appeared together as beautiful as a pair of “fairies and pearls” 32 years ago.

“The sexiest first date in Oscar history”

Michael Jackson and Madonna are inherently two legendary names in the world music industry. If Michael Jackson is the King of Pop, Madonna is no less competitive with the title of queen bestowed upon him by his fans.

And of course, their lives are also a song of ups and downs, filled with joy, anger, sadness, happiness, suffering, and even 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 hasty moment the “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 Oscars history, it would have to be Michael Jackson and Madonna” – that’s what Hollywood media dedicated to this special moment.

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


Later, Madonna talked about their special appearance at that time: “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 agreed saying it was great.”

In 2018, Madonna reposted a photo with Michael Jackson on her personal page and called 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 that had just begun ended quickly

Many years later, people are curious whether  Michael Jackson  and Madonna were ever together. Of the two people involved, one has left this life and the other rarely talks about that short period together. The rare time Madonna opened up about their relationship was probably at the Carpool Karaoke show.

Madonna said that she was the one who took the initiative in 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.” him more. I invited him to dinner, I said ‘Hello, I’ll drive – just you and me”.

Legendary moments of Hollywood in the 90s: The short-lived love affair of the "king and queen" entertainment village - Photo 3.

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

Legendary moments of Hollywood in the 90s: The short-lived love affair of the "king and queen" entertainment village - Photo 4.

“Then we came 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 looked like he was was looking for more of a friend than a romance, and I’m glad I could help with that. At the time, he didn’t feel like a superstar. He felt like a We hung out a few more times, then for one reason or another we lost touch.” Their budding love affair ended quickly.

Madonna admitted that she was really disappointed and hurt when she heard the news that her close friend had passed away on a sad day in London: ” I feel his pain, I know how it feels.” walking down the street and feeling like the whole world had turned its back on me. When I first heard about Michael’s death, I was in London, a few days from the start of my tour. Michael was going to perform in same place as me a week later. All I could think at that moment was: I abandoned him.”





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