Madonna Reportedly Thought John F. Kennedy Jr. Was "Slightly More Frightening" Than Sean Penn

The singer dated the political heir for six months in the '80s.

Madonna JFK Jr
Photo: Kip Rano/Shutterstock

With the 20-year anniversary of John F. Kennedy Jr.’s untimely death just weeks away, biographies and anecdotes about America’s premiere political heir are cropping up at every turn.

In one of the newest tomes concerning JFK Jr., The Kennedy Heirs, biographer J. Randy Taraborrelli delves into John’s romantic past, which, in addition to his marriage to wife Carolyn Bessette included relationships with starlets like Daryl Hannah, Sarah Jessica Parker, and Madonna.

Perhaps the least documented and most contentious of these relationships was Madonna’s. Madge, who loved to lean into the parallels between herself and Marilyn Monroe, was unsurprisingly not a big hit with John’s mom, Jackie Kennedy. In addition to the obvious, Jackie reportedly didn’t love Madonna’s adoption of catholic iconography into her style.

According to Taraborrelli, Madonna used to complain about John’s temper to her friends. They dated for six months, while she was separated from then-husband Sean Penn, whose own temper has been the topic of much discussion in the media. Madonna even reportedly filed an assault complaint against the actor in 1989, but dropped the charges soon after.

Taraborrelli writes that despite Penn’s checkered past, Madonna found Kennedy to be the “slightly more frightening” of the two.

“Whereas Sean would act out, perhaps give a photographer a body shot just to vent, somehow John’s way seemed more personal. Madonna said that he would get up in her face, maybe an inch away, and scream at her at the top of his lungs when they were in a fight,” Taraborrelli writes in The Kennedy Heirs.

Kennedy’s temper rarely reared its head in public, save for a brutal and highly public fight he and Bessette had in 1996.

“At one point, John snatched the engagement ring right off her finger,” Taraborrelli wrote of the scene. “It was ugly, the two pushing and pulling at each other while screaming and sobbing.”

Madonna and Kennedy remained on good terms, however, with John even reportedly asking the pop star to pose on the cover of his political and cultural magazine George years later, as his mother …

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