"Oh so you want me to kiss and tell": When Madonna opened up about her iconic date with Michael Jackson on Carpool Karaoke
There have been multiple iconic moments at the Oscars over the years, however, Madonna attending the 1991 Oscar Awards together with Michael Jackson remains in people's memories to this day. Madonna wore an outfit paying homage to Marilyn Monroe at the event, sporting jewellery reportedly worth $20 million.
The singer posed for the cameras holding the King of Pop's gloved hand, resulting in a story dubbing them 'The Oddest Couple' by People magazine that year. Recollecting cheeky details of her date with Michael Jackson during an episode of The Late Late Show With James Corden's Carpool Karaoke segment in December 2016, Madonna said:
"Oh so you want me to kiss and tell then, don't you?"
Elaborating on her date with Michael Jackson, Madonna shared that the two kissed, adding that she's never had the chance to talk about it because nobody asked her about it. James Corden asked the Hung Up singer about who made the first move, to which she replied:
"Well, I did if you wanna know the truth because he's a little bit shy. However, he was a willing accomplice. I did sort of get him to loosen up with a glass of chardonnay. And it worked wonders."
The singer added that she's never spoken about her date with Michael Jackson and what followed publicly. However, she talked about it with James Corden because she considered him a friend.
"He agreed and showed up to my house without any bodyguards": Madonna reflected on her time with Michael Jackson in emotional tribute
In addition to mentioning her Oscars date with Michael Jackson during her interview with James Corden, Madonna reflected on her time with the King of Pop at the 2009 Video Music Awards. In her emotional tribute talking about Michael Jackson after his demise in June 2009, the singer recalled a night out with the late celebrity.
Madonna mentioned that she couldn't call Michael Jackson her great friend, however, she wanted to know him better and hence decided to ask him out to dinner in 1991. She offered to treat Michael and drive him, adding she requested it only be the two of them on their night out.
Elaborating, Madonna said:
"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?'"
The singer continued:
"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."
Madonna added that for the rest of the dinner, she was hellbent on getting Michael Jackson to eat French fries, drink wine, have dessert, and use bad words, which were things that he didn't allow himself to do. The Frozen singer recalled that she and MJ went back to her house to watch a movie and that they sat on the couch like kids during which Michael Jackson's hand snuck over hers.
While it has been many years since the Vogue singer spoke about her time with MJ, the singer also recollected how she felt the first time she heard of Michael's demise. She said that MJ was going to perform at the same venue in London as her a week later, however, all she could think about at that moment was that she abandoned him.
