Throughout her groundbreaking career, Madonna – who recently made headlines for becoming the first female artist to score a top 10 album in every decade since the 1980s with Finally Enough Love – has always been considered the Queen of Pop. It was therefore inevitable she’d have crossed paths with  the King of Pop  at some point.

As two of the greatest entertainers of all time, Madonna and Michael Jackson did share a friendship. But what was the pop royals’ relationship really like?

They shared a manager who introduced them to each other

Michael Jackson first met Madonna when they were both in their early 20s and had the same manager. Photo: @drownedmadonna/Facebook

Madonna and Jackson met in the 1980s at the height of Jackson’s fame as a solo artist, when  Madonna’s stardom  was steadily rising. The pop music monarchs, who were coincidentally both born in August 1958, also shared a manager.

In a 2009 Rolling Stone interview, Madonna recounted how she was introduced to the “Billie Jean” singer: “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.”

In fact, Madonna revered Jackson so much she even confessed to working with DeMann just because he managed Jackson: “I thought ‘Who’s the most successful person in the music industry and who’s his manager? I want him.’”

They went on the “best date ever”

Michael Jackson and Madonna got fans excited when they went to the Oscars together in 1991. Photo: Getty Images

Though the superstars met in the 1980s and maintained a friendship for years afterwards, it wasn’t until 1991 when rumours started circulating about the nature of the famous pair’s relationship.

The media frenzy was sparked when the King and Queen of Pop, both wearing white, attended the 63rd Academy Awards ceremony together.

In a VH1 interview, the “Material Girl” singer detailed how that came to be: “Michael was like, ‘Well, who are you going to go with? I looked at him and said, ‘I don’t know. You want to go?’ And he said, ‘Yeah, that’d be great.’”

Madonna admitted to kissing Michael Jackson on James Corden’s Carpool Karaoke segment. Photo: Getty Images

Years later Madonna shared on Instagram a snapshot of the night, captioned: “Best Date Ever!!”

Then in 2016, on Carpool Karaoke, Madge admitted she and Jackson kissed. When host James Corden asked, “Did you kiss?” The “Hung up” singer responded, “Of course, I mean baby, I’ve been around.”

They were spotted out together and almost collaborated on a song

Michael Jackson and Madonna were seen out together several times in the early 1990s, seen here leaving The Ivy restaurant together. Photo: Liaison

After their hyped Oscars outing, per British media, the two musicians were seen out together a handful of times, fuelling rumours that the pair were dating. However, it didn’t last and they weren’t seen together again afterwards.

In the Rolling Stone interview, Madonna described their relationship:

“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,” she recalled. “So that’s what we were doing: watching movies, having dinner, hanging out, going to the Oscars, being silly, seeing if we could work.”

Madonna further revealed that the two almost collaborated on “In The Closet”, Jackson’s song for which she’d been asked to compose lyrics: “I started writing words and getting ideas and stuff and I presented them to him and he didn’t like them.”

Their friendship fizzled out

While for a hot second it seemed like there might have been a union of majestic proportions, the King and Queen of Pop’s relationship ended abruptly.

One of the purported causes of the fallout was divulged by producer Kenneth “Babyface” Edmonds during a 2020 Verzuz online rap battle with Teddy Riley, who co-produced MJ’s “In The Closet”.
“Babyface, can you believe she [Madonna] wants me to dress like a girl?” Edmonds recalled Jackson saying. “He was like, ‘I’d never do that.’ He said, ‘She was trying to change it all up. It was crazy.’ He was really mad about it.”

Other incidents might also have caused the relationship’s decline, some of which were detailed in The Michael Jackson Tapes: A Tragic Icon Reveals His Soul in Intimate Conversation, a series of personal recordings between Jackson and his spiritual adviser, Rabbi Shmuley Boteach.

“She is not a nice person,” the Moonwalk maestro said, remembering how he and Madonna had argued:

“Madonna laid the law down to me before we went out. [She said,] ‘I am not going to Disneyland, OK? We are going to the restaurant. And afterwards, we are going to a strip bar.’ I said, ‘I am not going to a strip bar, where they crossdress.’ Afterwards, she wrote some mean things about me in the press. And I wrote that she is a nasty witch, after I was so kind to her.”

Jackson also referred to an incident when a child had come up to the two stars at a dinner and Madonna reportedly snubbed the young fan.

“Don’t you ever talk to children like this,” Jackson told Madonna.

“She said, ‘Shut up,’” he recalled. “I said, ‘You shut up.’”

Madonna praised and defended Jackson after his death

Madonna had Michael Jackson impersonator Kento Mori perform during the opening night of her Sticky and Sweet tour a month after Jackson’s death in 2009. Photo: WireImage

Even if the King and Queen of Pop’s amicable relations were short-lived, it’s clear the “Vogue” superstar admired and respected her celebrated male counterpart.

“I can’t say we were great friends,” Madonna said in a moving tribute speech at the 2009 VMAs after Jackson’s death. “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.”

“In that moment,” Madonna continued, “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. Yes, Michael Jackson was a human being but he was a king. Long live the king.”

Finally, in a British Vogue interview, Madonna was asked to comment on allegations made in 2019’s Leaving Neverland documentary. “I don’t have a lynch mob mentality, so in my mind, people are innocent until proven guilty.”