In a strange bit of pop culture we’ve seen before, two names back on everyone’s lips this summer are Madonna and Michael Jackson.
Antoine Fuqua, Jackson biopic Michaelstarring his nephew Jafar Jackson, has just given a huge global opening for a musical biopic. Meanwhile, Madonna is back in circulation, coming off a Coachella appearance and teasing new music with Sabrina Carpenter.
Which makes this a useful moment to revisit the period when the world’s two biggest pop stars briefly tried to operate in the same orbit.
In the last episode of The wonderful othersSuper-manager Freddie DeMann, who worked with Jackson from 1978 to 1983 and Madonna from 1983 to 1997, provided a telling recollection. Recalling a meeting with Jackson in a Paris hotel suite in 2008, Jackson’s parting message states: “Tell your girl she forgot the tunes.”
Even then, Jackson was still tracking Madonna’s choices, weighing them against his own instincts. Their dynamic has always had that edge to it.
Their most famous moment came at the 1991 Academy Awards, when they arrived together, hand-in-hand, on each other’s date. Madonna turned to Marilyn Monroe iconography for her performance of “Sooner or Later.” Jackson appeared wearing a white jacket embroidered with gold embellishments and a cane. The images moved instantly.
Madonna later said that they went home together after the Vanity Fair party. Years later, she told James Corden that she had kissed him and tried to show him how to do it better. She also had notes on his photo. She wanted a haircut. She wanted him to rethink the stockings, the loafers, the whole show.
Contact briefly extended to the studio. “In the Closet” from 1992 dangerousgrew out of early conversations with Madonna, who pushed for a more overt sexual direction and pitched ideas for the video, including the concept of a role reversal where she would present as male and Jackson as female.
According to producer Kenneth “Babyface” Edmonds, Jackson shut it down immediately. “Can you believe she wants me to dress like a girl?” He remembers Jackson saying. “I would never do that.”
The collaboration ended there. The song featured a different vocalist credited as “Mystery Girl”, who was later revealed to be Princess Stéphanie of Monaco. The Herb Ritts-directed video paired Jackson with Naomi Campbell and relied on a stylized, restrained visual language.
By that point, the relationship had already begun to unravel. In recorded conversations with Rabbi Shmuley Boteach, Jackson described an early clash during a night out. He said Madonna made the plan: dinner, then a strip club. He refused. “If so, forget the whole thing,” he said.
He later claimed that she had written about him negatively in the press. He responded and called her a “bad witch.” Madonna later confirmed the encounter and said he also called her a “cow” during a phone call.
What Deman’s story confirms is how long this tension lasted. Years later, Jackson was still thinking about her work, still interacting with it in real time. Both artists were used to controlling and building their careers shaping every aspect of their image and output.
However, place them close to you, and the friction was instantaneous. Madonna wanted to modify it. Jackson wanted her to get back toward something he valued. The relationship never settled into anything stable.
What remains is a short, strange chapter in which two of popular culture’s most dominant figures share space, test each other, and part ways. To the end, Jackson was still providing feedback.
