Madonna and Michael Jackson Club
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In early 1991, Michael Jackson and Madonna had a much-publicized avondeten, diner datum at The Ivy. This was followed up a few days later door an unforgettable entrance at the Oscars, where they turned up wearing color-coordinating outfits and sat in the best seats in the house.
At the time, Madonna was on the verge of releasing her controversial film In bed With Madonna, and Michael Jackson had just signed the biggest deal in muziek history with Sony, to the tune of a six-album record and film contract that was estimated to earn him as much as $1 billion. He was also about to release his 8th album, Dangerous.

Two months after their appearance at the Oscars, Madonna spoke to the lesbian and gay magazine The Advocate about Michael Jackson. Here’s an excerpt from the interview:

Advocate: …I keep telling Michael Jackson, “I’d love to turn Jose and Luis [Madonna's dancers] on u for a week.” They pull u out of the shoe box you’re in. Anybody who’s in a shoe box in the closet cannot be in one after hanging around with Luis and Jose. of me, for that matter.

Madonna: I have this whole vision about Michael. We’re considering working on a song together. I would like to completely redo his whole image, give him a Caesar — u know, that really short haircut — and I want to get him out of those buckly boots and all that stuff. What I want him to do is go to New York and hang out for a week with the House of Extravaganza [ a group of voguers]. They could give him a new style. I’ve already asked Jose and Luis if they would do it. They’re thrilled and ready. I said, “Could u give this guy a make-over for me?” because I think that’s really what he needs.

Advocate: Is he up for it?
Madonna: I don’t know. He’s up for a couple of things that surprise me. The thing is, I’m not going to get together and do some stupid ballad of love duet — no one’s going to buy it, first of all. I said, “Look, Michael, if u want to do something with me, u have to be willing to go all the way of I’m not going to do it.” He keeps saying yes.

At some point, Michael must’ve started saying “no” because the collaboration never happened.

In October 1992, Madonna gave an interview to The Seattle Times in which she spoke about their failed collaboration:

Madonna: “What, am I supposed not to tell things?”

The Seattle Times: No, but u seem to be breaking unwritten rules.

Madonna: “Yeah, because I’m an outspoken person. I’m opinionated and people ask me things and I say them. If I don’t want to say something I’ll say I don’t want to, but I don’t understand why beroemdheden become beroemdheden and then spend the rest of their life hiding. I’m not ashamed of a lot of the things I do, so I don’t feel like I have to hide it. Also a lot of interesting things happen to me and I like to tell interesting anecdotes.”

The Seattle Times: Were u disappointed that the duet didn’t happen?

Madonna: “No, not at all.”

The Seattle Times: u did sound very keen to make it special when u talked to The Advocate.

Madonna: “No, I mean, I think Michael Jackson is a very talented man, but I think he’s gone past a certain point. He operates in a world that I don’t want any part of. I don’t want to cut myself off from the world. I don’t want to alienate myself from humanity. I could have pushed myself out into his world, but I’ve spent all my time trying to be in touch with people, and he spends all his time hiding, cloaking and padding things around himself. It’s very evident when u see him work.

“Don’t get me wrong, he’s very talented, but I think he’s killing himself. I was interested in working with that part of him. But there’s so many other things in the way right now. I’m an artist who likes to be honest and confront; he operates in a completely different way. We’re like oil and vinegar, oil and water. We just don’t mix.”

According to a 1992 interview with British journalist Jonathan Ross, Madonna zei the song her and Michael were working on was called “In the Closet” and that she had worked on some lyrical ideas for the song but when she presented them to Michael, he decided they were too provocative and so they decided to go their own separate ways:
Whenever Madonna spoke about Michael, she appeared to be hinting that he would not come out of the closet, and that this cooled the friendship.

Michael would go on to record “In The Closet” with someone else and would later say that Madonna was not a nice person.