Madonna reveals she kissed Michael Jackson by 'loosening him up with a glass of chardonnay'

Madonna drops a bombshell about her brief romance with Michael Jackson—and how she had to make the first move
PUBLISHED FEB 28, 2025
Madonna and James Corden in a still from 'Madonna Carpool Karaoke' December 2016; (inset) MJ at the Amsterdam ArenA - HIStory Tour 1997. (Cover Image Source: YouTube| The Late Late Show With James Corden; (inset) Getty Images| Photo by Michel Linssen)
Madonna and James Corden in a still from 'Madonna Carpool Karaoke' December 2016; (inset) MJ at the Amsterdam ArenA - HIStory Tour 1997. (Cover Image Source: YouTube| The Late Late Show With James Corden; (inset) Getty Images| Photo by Michel Linssen)

Madonna and Michael Jackson shared quite a history; they were first introduced to each other by their manager Freddy DeMann in the 80s. The 'King and Queen of Pop' made a sensational debut together on the Oscar red carpet in 1991 and were briefly involved in a publicized relationship. Decades later the 'Like a Prayer' hitmaker spilled romantic details about her late ex while appearing in James Corden's 'Carpool Karaoke' segment. "You were dating Michael Jackson?" the comedian prodded in between their fun karaoke session. "I was," Madonna replied. "What was a night out with MJ or was it a night in?" he pushed further. "You want me to kiss and tell then, don't you?" the 'Material Girl' teased. "Did you kiss?" Corden asked astonished. "Of course," Madonna calmly replied. 



 

The late-night show host couldn't believe his ears and got excited to know who initiated the first move. "I did not know that," he exclaimed. "Well, I haven't had the chance to talk about it. No one ever asks me," Madonna candidly complained. "So hang on. Who made the first move, you or MJ?" "Well, I did, if you want to know the truth because he's a little bit shy," the 'Frozen' singer confessed. She then revealed that they made out after having a glass of chardonnay, "However he was a willing accomplice. I did get him to sort of loosen up with a glass of chardonnay. And it did wonders."

Michael Jackson and Madonna at Ivy restaurant 1991. (Image Source: Getty Images| Photo by Barry King)
Michael Jackson and Madonna at Ivy restaurant 1991. (Image Source: Getty Images| Photo by Barry King)

Madonna acknowledged that, except for one of her friends, she had never discussed this with anyone, "I mean but now you're my friend. So now I have said that to another friend," she quipped to Corden. "I love that," he replied. Fans of the show couldn't get enough of her relationship with the 'Beat It' hitmaker, "I feel like Madonna has so many secrets and no one ever asks her the right questions like How has no one ever asked her about MJ," a viewer pointed out in the YouTube comment section. "It’s nice that Madonna still defends MJ, even after the things Michael said about her she still stood by him," a fan chimed. "I wish MJ was still alive and do the Karaoke with James," an online user wished. As per SCMP, after their Oscar debut as a couple Madonna and Jackson were spotted several times on date. 


 
 
 
 
 
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They were even supposed to collaborate on a single titled 'In The Closet' but Jackson rejected the 'Hung Up' singer's lyrics because they were too raunchy. “I started writing words and getting ideas and stuff and I presented them to him and he didn’t like them,” she revealed then. Their personalities did not match, and the 'IT' couple soon separated, Jackson blamed Madonna for dragging him into 'dressing like a girl' which he did not accept. “Can you believe she [Madonna] wants me to dress like a girl?” he told producer Kenneth Edmonds then, as per NME.



 

During his chilling taped conversations with Rabbi Shmuley Boteach, Jackson disclosed that their fleeting romance ended because she wanted to take him to a strip club where the crowd mostly came crossdressed. When he refused Madonna reportedly gave petty interviews insulting him, and Jackson retaliated by calling her a "nasty witch." "I said, ‘I am not going to a strip bar, where they crossdress." The 'Smooth Criminal' singer also did not like her behavior when a child fan came up to them for autographs and Madonna dissed him, Jackson got provoked and scolded her. However, the 'Like a Virgin' singer defended their bond after his death and paid a moving tribute during the 2009 VMAs.

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