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Biographer makes penis claim about dead celebrity Madonna said was ‘best sex ever’
Home>Entertainment>Celebrity
Updated 12:21 1 Jun 2026 GMT+1Published 12:05 1 Jun 2026 GMT+1

Biographer makes penis claim about dead celebrity Madonna said was ‘best sex ever’

The Grammy-winning singer's late lover had her hitting high notes - and not in the musical sense

Olivia Burke

Olivia Burke

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Although discussing the anatomy of a dead man is considered to be uncouth, it's all people can talk about at the minute in wake of Madonna's X-rated admission.

The 'Queen of Pop' shared some very intimate details about one of her famous former lovers last week, so naturally, fans have been desperate to find out more about him.

And given that the bloke in question is John F Kennedy Jr, there's a lot of information available, as his name often crops up in history books - while a biographer who previously delved into his life also dished some dirt.

A few days ago, 'Vogue' hitmaker Madonna was sat down with Ivy Mugler, Raul Lopez, Jeremy O. Harris, Bob the Drag Queen and Marcelo Gutierrez for a video with dating app Grindr where she was asked some personal questions.

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While promoting her new album Confessions II, the singer was asked to give a shoutout to the best lover she has ever had the pleasure of sharing a sexual encounter with.

She agreed to comply, but said the stipulation was that she would 'only name dead people' - and then, she name-dropped John Kennedy Jr.

JFK Jr's bedroom antics left a lasting impression on Madonna (Barry King/WireImage)
JFK Jr's bedroom antics left a lasting impression on Madonna (Barry King/WireImage)

The pair had a fling back in the 1980s when her marriage with actor Sean Penn was coming to an end, although details of their brief relationships are few and far between.

The only insight we've ever gotten into the dynamic between Madonna and Kennedy is from biographers, who claim to have got the scoop from insiders close to the pair.

For example, the 2024 book JFK Jr.: An Intimate Oral Biography alleges that the seven-time Grammy winner 'came onto him', using 'flattery' to woo the son of President John F. Kennedy and First Lady Jackie O.

"He loved her body," the authors claimed. "It was all about physical attraction; it wasn’t going to be anything beyond that."

As well as Madonna's recent confession sparking renewed interest in Kennedy's private life, Ryan Murphy's series Love Story: John F. Kennedy Jr. & Carolyn Bessette had the same impact earlier this year.

The nine-episodes, which are available to stream on Hulu and Disney+, delves into the 'undeniable chemistry, whirlwind courtship and high-profile marriage' of the pair - and how it came to a heartbreaking end.

The former lovers seen chatting together in June 1997 (Michael Brennan/Getty Images)
The former lovers seen chatting together in June 1997 (Michael Brennan/Getty Images)

The FX show was inspired by Elizabeth Beller’s book, Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy.

Murphy received a fair bit of flack for Love Story and it's alleged inaccuracies, including from Kennedy's nephew, Jack Schlossberg.

Following it's release in February, the political commentator said during an appearance on CBS Sunday Morning: "Well, if you want to know someone who’s never met anyone in my family, knows nothing about us, talk to Ryan Murphy. I would just want people who do watch the show to watch it with one letter in mind, and that’s a capital F for fiction.

"The guy knows nothing about what he's talking about, and he's making a ton of money on a grotesque display of someone else's life."

Biographer Maureen Callahan shared a similar sentiment about Love Story and how Kennedy was portrayed in the show - particularly when it come to depicting the late businessman's supposed coyness about explicit matters.

Ryan Murphy's series had a few inaccuracies about the late attorney, biographer Maureen Callahan claimed (FX)
Ryan Murphy's series had a few inaccuracies about the late attorney, biographer Maureen Callahan claimed (FX)

In one scene, JFK Jr is seen discussing the media storm surrounding his personal life with his cousin Anthony Radziwill in a locker room.

He explains that he 'can’t show his face around the city with these headlines everywhere', while his relative then jokes that he isn't fussed about 'showing his d*ck to everyone at the gym'.

The actor who played Kennedy, Paul Anthony Kelly, then retorts: "Apparently, that’s all I’m good for." But according to Callahan, these words would have never left Kennedy's mouth.

The author, who penned the 2024 book Ask Not: The Kennedys and the Women They Destroyed, reckons that Murphy's production had 'many problems', including it's interpretation of how Kennedy would have engaged in locker room talk.

During a previous episode of her podcast, The Nerve With Maureen Callahan, the writer said: "John Jr. was such an exhibitionist...So, you’re going to tell me, 'the big bad media'? He loved the media attention.

"He loved nothing more than ripping off his shirt and running around in Central Park, okay? And making sure all the paparazzi got great views, okay? Great sight lines."

Callahan went on to claim: "He would walk around the gym naked all the time. Like picking at his pubic hair and inspecting his genitalia, like teasing other men."

Kennedy Jr died in 1999 along with his wife Carolyn Bessette-Kennedy, and sister-in-law Lauren Bessette, when the plane he was piloting crashed into the Atlantic Ocean off the coast of Martha's Vineyard, Massachusetts.

Featured Image Credit: Kevin Mazur/Getty

Topics: Madonna, Celebrity, Sex and Relationships, John F. Kennedy

Olivia Burke
Olivia Burke

Olivia is a journalist at LADbible Group with more than five years of experience and has worked for a number of top publishers, including News UK. She also enjoys writing food reviews (as well as the eating part). She is a stereotypical reality TV addict, but still finds time for a serious documentary.

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@livburke_

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