Michael and Madonna: The King and Queen of Pop

Michael and Madonna: King and Queen of Pop at the 1991 Oscars.


Once again we take a peek into the relationship of two of the most controversial, misunderstood people. The King and Queen of Pop.  

This comparison isn’t so much a battle between who’s better, but instead a look at the bond the two shared, or rather- didn’t.  

As usual, we begin with the similarities (or in this case the differences), what made these two polar opposites. You could say it was written in the stars!  

Michael and Madonna were both born to large families in August of  ’58, and even lived in neighboring states (Michael: Indiana, Madonna: Michigan). Although Madonna had the fortune of a childhood, she had so without her birth mother who passed away from breast cancer when Madonna was five. Michael, already an icon at an early age, spent his premature adulthood growing up in the spotlight. All the while being struggling to keep childlike innocence.  

Speed ahead a decade or so, and Madonna is a full-blown star now crowned “Queen of Pop” and in her prime. Looking at Michael, we see a seasoned veteran in his late twenties. The two are now controversial sensations and irresistible to the tabloid media.  

Although, Madonna did confess to being a bit of a fan girl the first time she encountered Michael Jackson[‘s talent], she’s also openly admitted her admiration for his song-writing capability and became all the more intrigued by Michael. (Can you blame her?)  

Madonna later got the opportunity to meet with Jackson early on in her career, and recalled their very first encounter.  

“I met him in the early ’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.”  

When Michael and Madonna were seen out in public together in the early nineties, the back story leading up to the date, was as interesting as the date itself on that unforgettable Oscar night.  

 It’s been told, Madonna called up Michael for a rendezvous, and told Michael her expectations, and it went a little something like this: 

Madonna: “I’m not going to %$#&*ing Disneyland.”  

Michael then replied, taking as stern a stand as Madonna…  

Michael: “I didn’t ask you to go to Disneyland.”  

Later in the evening, he laid down the law. “I told her, I am NOT looking at those spanky books. I am NOT going to a strip club where guys are dressed like girls and girls like guys.”  

 You can guess after that, Michael thought of Madonna as nothing short of a ‘wild child.’ Especially after stunts like this: “How would you like getting a phone call and she is telling you that she is putting fingers between her legs. I would say, “Oh Madonna, please.” She said, “What I want you to do when I hang up the phone is to rub yourself and think of me.” “That’s the kind of stuff she says. She does. When I see her she says, “This is the finger I used last night.” “Wild, out of control.”  


(It might do some good to mention right about now that some of these quotes and various what- nots are from Rabbi Boteach’s “The Michael Jackson Tapes.” While the so-called spiritual advisor is out spreading Michael’s secrecy, I wonder how he couldn’t feel any remorse for even thinking about betraying Michael’s trust. He’s a rabbi for cryin’ out loud. I don’t know about you, but if I’m going to my spiritual advisor for advice, for whatever reason, I assume the strictest confidentiality.  How could he live with himself knowing he’s betrayed the trust of someone who has been mercilessly judged, ridiculed, and hurt by the lies being spread about him? Some “friend.”)  

Anyway, despite their differences in nature, they managed to make an attempt to cross paths again.  

“Like most performers he was shy and plagued with insecurities. 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, I said “My treat, I’ll drive — just you and me.”  

He agreed and showed up to my house without any bodyguards. We drove to the restaurant in my car. It was dark out, but he was still wearing sunglasses.  

I said, “Michael, I feel like I’m talking to a limousine. Do you think you can take off your glasses so I can see your eyes?”  

Then he tossed the glasses out the window, looked at me with a wink and a smile and said, “Can you see me now? Is that better?”  

In that moment, I could see both his vulnerability and his charm. The rest of the dinner, I was hellbent on getting him to eat French fries, drink wine, have dessert and say bad words. Things he never seemed to allow himself to do. Later we went back to my house to watch a movie and sat on the couch like two kids, and somewhere in the middle of the movie, his hand snuck over and held mine.  

It felt like he was looking for more of a friend than a romance, and I was happy to oblige. In that moment, he didn’t feel like a superstar. He felt like a human being.”-Madonna, 2009 MTV Awards  

While getting well acquainted with one another, Michael brought up the idea for he and Madonna to do a collaboration on “In the Closet.” Michael asked Madonna to write some lyrics for her part in the song, but Michael deemed them too explicit, therefore chances of any collaborating would quickly turn into unusable material short of porn. Of  course, the duet never was, and afterwards, both managed to get on with their lives. 


Last year, Madonna, like many other artists, paid homage to Michael and explained what he meant to her. What sets her apart from the rest of the bunch, is her speech at the 2009 MTV Music Awards. 

All in all, the relationship the two shared was adoring on Madonna’s part, and teasingly curious on Michael’s. To Madonna, Michael was a ”thrilling” king who she admits to abandoning, and to Michael… she was a crazy person. 

To read Madonna’s speech dedicated to Michael, click below. 




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