Madonna remembers her late ex John F. Kennedy Jr. fondly — very fondly.
Madonna, 67, teamed up with LGBTQ+ dating app Grindr for a new video promoting her upcoming album, Confessions II. In a sneak peek obtained by Page Six on Thursday, May 28, fashion designer Raul Lopez asked the Queen of Pop to name the “best d***-down” she has ever experienced.
“I’m only going to name dead people,” Madonna replied before covering her mouth and whispering, “John Kennedy Jr.” (The son of former President John F. Kennedy died in a plane crash in 1999 at age 38.)
Lopez noted that “everybody says [Kennedy’s] d*** was crazy and he was a good f***,” telling the “Like a Virgin” singer, “You’re the third person I’ve heard say that.”
Madonna then simply confirmed, “Mm-hmm.”
The seven-time Grammy winner’s other late exes include artist Jean-Michel Basquiat and rapper Tupac Shakur.
Madonna briefly dated Kennedy in the late 1980s as her infamously turbulent marriage to Sean Penn was coming to an end.
“She came on to him, and it was flattery. She was at the top of her game,” an unnamed friend recalled in the 2024 book JFK Jr.: An Intimate Oral Biography by Kennedy’s executive assistant RoseMarie Terenzio and People editor-at-large Liz McNeil. “He loved her body. It was all about physical attraction; it wasn’t going to be anything beyond that.”
However, after just one date, Kennedy was said to be infatuated with Madonna.
“The dashing, dark, muscular Kennedy gave her a set of keys to his apartment,” biographer J. Randy Taraborrelli wrote in his 2012 book, After Camelot.
JFK Jr.’s mother, Jacqueline Kennedy Onassis, allegedly disapproved of the attorney’s fling with the “Vogue” singer.
“[Jackie’s] problem with [Madonna] was that she was married,” Taraborrelli told People in 2023, claiming Kennedy Onassis was also “confounded by Madonna’s penchant for attention.”
The author explained, “Jackie had spent her entire celebrity life avoiding paparazzi, whereas Madonna would court paparazzi. And Jackie just couldn’t understand any of that.”
While Madonna and Kennedy ultimately went their separate ways, he famously asked her to pose as his late mom on the cover of his political magazine, George, in 1996.
“‘Wouldn’t that be a riot?'” JFK Jr. asked Terenzio, according to her 2012 memoir, Fairy Tale Interrupted. “‘We’ll have her in the pillbox hat, sitting on a stack of books. … If it doesn’t bother me, why should it bother anyone else?'”
The book noted that Madonna responded by fax the following day, declining to dress up as Kennedy Onassis and joking, “My eyebrows aren’t thick enough, for one.”
