As two legendary artists born in the same year and month and suffering many losses in their childhood, Michael Jackson and Madonna once had a relationship that was more than friendship.

Madonna and Michael Jackson are two legends in the world of music. They were trained under the same roof by manager Freddy Demann, worked together on many music projects, and developed feelings for each other from a very young age.

When talking about Michael Jackson, the Queen of Pop always reserved the most affectionate words. She said it was his natural talent that made her develop a sympathy that is difficult to put into words.

“I fell madly in love with him, completely losing my mind. He was really talented. The songs he sang were not childish at all,” she recalled emotionally.

“The moment he started singing at just 8 years old, you could feel like an adult was squeezing your heart…His music had layers of magic that not only made you want to dance, but also made you believe that you could fly, dare to dream, and be whoever you wanted to be.”

Michael Jackson and Madonna appear at an event. Photo: Billboard.

Michael Jackson and Madonna appear at an event. Photo: Billboard.

budding love

Shortly after, Madonna officially entered the American music world, meeting her idol for so long. “I met him in the early 1980s, when I first started working with Freddy DeMann, who was also managing Michael Jackson at the time.”

“I saw him play at Madison Square Garden and I was so overwhelmed. We met again that night at a party at the Helmsley Palace Hotel. He was so shy and I was so nervous,” she recalled.

After that, the two began to share many similarities in life, from being born in the same year and month, to working in the art field, or being the top idols of young people at that time.

“We dated for a while. He wanted to work with me, I think he wanted to get to know me better and I wanted to know him better,” she said.

Michael Jackson and Madonna were caught having dinner together. Photo: DailyMail. 

After much hesitation, thought and worry, the two finally came together and shared many happy moments together. They watched movies, had dinner, went for walks, went to the Oscars together and even considered collaborating on a music product.

First kiss

With their affection growing over the years, the two pop kings shared their first kiss, which Madonna only revealed recently on Carpool Karaoke.

When Corden asked in surprise, “Don’t tell me you kissed Michael Jackson?”, the 58-year-old star confessed: “Of course, man. I just haven’t had a chance to talk about it, because no one asked.”

Continuing the story, the singer of Like a Virgin said that she was the one who took the initiative to flirt with the other person because “he was a bit shy at that time”.

“But he was also willing to be an accomplice,” the diva added. “I got him to loosen up with a glass of chardonnay. And it worked wonders.”

Michael Jackson and Madonna bonded and became close to each other due to many similarities in life and work. Photo: Just Jared.

If they were connected by strange ties from childhood to their illustrious careers, Madonna and Michael Jackson’s love affair quickly ended because of an interview. In it, the pop queen expressed her disapproval of Michael Jackson’s fashion style and suggested that he try a new, more suitable style.

After this incident, Jackson felt so humiliated that he never spoke to his former girlfriend again. Insiders said that the King of Pop was “extremely angry” that she “dared” to degrade the style that made his name.

Tragic ending

Although the relationship ended quietly, Madonna still expressed her feelings about her ex. She once devoted her entire VMA speech to Michael Jackson, emphasizing that their difficult childhood was what brought them together.

“It’s good to have a quiet childhood, to be able to judge yourself before being influenced by what others say. That’s when you can make mistakes because of your own innocence, and then later, you can be more confident. But Michael Jackson was different. He didn’t have that lucky start.”

“Would he have a sense of self if he were outside the circle of fame and admiration? I think he felt insecure about the attention he was getting, and the love and hate of the work he was doing,” she said.

Despite a good start, the relationship between Michael Jackson and Madonna soon ended in silence. Photo: InStyle.

As one of the people closest to the late star, Madonna also confirmed that throughout his life, Michael Jackson had almost no close friends. In the last ten years of his life, he was almost ostracized when people labeled him crazy.

“A lot of people have said a lot of untrue things about me, so I never had any faith that the accusations against him were true. But maybe he didn’t know how to handle them, whether publicly or privately, and it destroyed him.”

“When he died, everyone talked about what a genius singer he was, but it’s important to appreciate people before you lose them. It’s such a tragedy,” the diva said.