Why Did Michael Jackson and Madonna Break Up?

Regarded as Queen of Pop, Madonna is recognized for her reinvention and versatility in making music, songwriting, and visual presentation. Her lyrics often center around social, political, s*xual, and religious themes, which have not only generated controversies but have also been critically acclaimed. She is often referred as a cultural icon who has been a major influence in the music industry in the 20th and 21st centuries. The Rock and Roll Hall of Fame described the artist as one of the most well-documented figures of the modern age.

Just like how Madonna’s music has garnered attention over the years, making her one of the most influential artists worldwide, her relationships have also been under the public microscope. Madonna has been married twice: to Sean Penn and then to Guy Ritchie. But she’s also been linked to other celebrities who are quite influential, including Michael Jackson.

Madonna recalled her ‘best date ever’ with Michael Jackson

King of Pop Michael Jackson and Queen of Pop Madonna had grown to be the biggest pop star in the 1990s. With their music and personalities, the two of them were known to be not only influential but also well-respected and loved artists in the industry. The two of them met in the 1980s via their manager, Freddy DeMann, as Madonna shared in a 2009 Rolling Stone interview (via SCMP)

I met him in the 80s when I first started working with my manager, Freddy DeMann, who at the time was managing Michael Jackson. I saw him play at Madison Square Garden, and I was blown away. He was flawless. There was a party at the Helmsley Palace Hotel. He was very shy, but it was a thrill for me.

After meeting through their manager, the two pop stars maintained their friendship over the years until 1991, when rumors about the two of them being more than friends started to circle. The two of them walked the red carpet at the 63rd Academy Award, donning a white outfit, looking like a pair from heaven. Madonna dressed to pay homage to Marilyn Monroe. The Queen of Pop later went on to recall how the two of them ended up being each other’s date.

Michael was like, ‘Well, who are you going to go with?’ I looked at him and said, ‘I don’t know. You wanna go?’ And he said, ‘Yeah, that’d be great.’ And then yes, he took me home.

Years later, sharing a picture from the night Madonna captioned it ‘Best Date Ever’. During her appearance on Carpool Karaoke with James Corden in 2016, when Madonna was asked if they kissed, she said, ‘Of course baby, I’ve been around.’

The two of them were spotted a handful of times, fueling the rumors of them dating, but then they weren’t seen together again. Talking about them being spotted together, Madonna in her Rolling Stone interview shared (via SCMP),

There was a period of time when we hung out. He wanted to work with me; I think he wanted to get to know me, and I wanted to do the same. So that’s what we were doing: watching movies, having dinner, hanging out, going to the Oscars, being silly, seeing if we could work.

The artist mentioned the late King of Pop, and she almost worked on In the Closet song, and when she presented her ideas and lyrics to him, he didn’t like them.

Madonna says Michael Jackson was looking for a friend more than romance

After their couple of outings, reports suggested that MJ and Madonna’s friendship fizzled out, and Kenneth ‘Babyface’ Edmonds, who co-produced In The Closet, recalled (via Verzuz),

MJ said, ‘Babyface, can you believe she wants me to dress like a girl?’ He was like, ‘I’d never do that.’ She was trying to change it all up. It was crazy.’ He was really mad about it.

The Michael Jackson Tapes: A Tragic Icon Reveals His Soul in Intimate Conversation revealed the conversation the King of Pop had with his spiritual adviser, Rabbi Shmuley Boteach. In the recording, fans can hear the artist mentioning that Madonna took him to a strip club, a place he didn’t want to go. MJ added that she wrote some mean things about him in the press, and he wrote that she was a nasty witch even though he was so kind to her.

Madonna, on her part, never really commented on the tapes or Babyface’s comment, but she did praise and defend MJ at the Video Music Awards in 2009 after he passed away. She said,

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

She acknowledged by stating that they went out a few more times and then they fell out of touch, and the witch hunt began with negative stories coming out one after the other about MJ. She added that she felt his pain as she understood what it was like to walk down the street and feel like the whole world was against you.

The artist in her tribute mentioned that when MJ was trying to build a family and rebuild his career, the public was passing judgment, and most of them (including her) had turned their backs on him. She recalled that she went back to watch some old videos and realized that he was unique, original, and so rare. The singer concluded by stating that there will never be anyone like MJ.