Madonna Once Recalled The Night She Seduced Michael Jackson Over an Evening of Wine: "It Worked"

Madonna once opened up about a time she had a romantic moment with Michael Jackson. The Material Girl described the situation of their past liaison during an appearance on James Corden's popular Carpool Karaoke segment in 2016. "Baby, I've been around," Madonna told Corden casually when asked if she and Jackson had ever kissed. She admitted they shared more than just a peck and went on to describe it as "tongue-in-mouth kissing."

The news hit a lot of fans by surprise, especially since so many people had been guessing what kind of relationship Madonna and Jackson had for years. The two music icons were seen together at the 1991 Academy Awards and it got people talking. Rumors about a possible romance started flying around after that moment. Neither had publicly confirmed any intimate involvement until the Carpool Karaoke episode. Madonna didn't shy away from the details. She confessed to making the first move on the notoriously shy Jackson. "Well, I did, if you wanna know the truth," she said. "Cause he was a little bit shy," as per Page Six. 

According to Madonna, a little liquid courage did the trick. "I did get him to loosen up with a glass of Chardonnay," she revealed. "And it did. It worked wonders." The singer seems surprised that no one had ever asked her about this previously, as the sight of these two celebrities enjoying a moment may have been exciting news at the time.  "I haven't had the chance to talk about it, no one ever asks me," she told Corden. It's hard to imagine such a juicy piece of pop culture history going unnoticed for so long. Madonna described Jackson as a "willing accomplice" once he relaxed a bit.

Their appearance together at the 1991 Oscars provides a potential timeframe as Madonna didn't specify exactly when this encounter took place. During the Carpool Karaoke segment, Madonna also touched on what she looks for in a partner nowadays. "Well, you have to have a sense of humor and understand my sense of humor. Otherwise, we are dead in the water." She also added, "I think the best thing in the world is to be married to someone funny." The 66-year-old singer, known for pushing boundaries throughout her career, surprised some viewers by describing herself as "quite square" in her personal life. "My work is rebellious but my lifestyle is not rebellious," she insisted to a skeptical Corden.

Madonna and Jackson were two of the most popular stars of the 1980s and 1990s. Lisa Marie Presley, who was Jackson's ex-wife, wrote in her memoir From Here to the Great Unknown, which her daughter completed after her death, that Jackson once told her, "Madonna had tried to hook up with him once, too, but nothing happened." He also told her, "I was terrified because I didn't want to make the wrong move," as per People.