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Published 14:33 11 Jun 2026 GMT
Jack Schlossberg has found himself reluctantly commenting on new claims about John F. Kennedy Jr., after Madonna said the late political figure was the “best sex” she had ever had.
The resurfaced attention came after Madonna took part in a Q&A on Grindr, where fashion designer Raul Lopez asked her: “What was your best fk? Who was your best dk-down?”
She replied that she would only name deceased partners, saying: “I’m only going to name dead people... John Kennedy Jr.” Designer Marcelo Gutierrez then added he had also heard positive stories about Kennedy Jr., to which Madonna responded: “So you know it’s true.”
Schlossberg was later asked about the comments during an appearance on SiriusXM’s Andy Cohen Live, where he was questioned: “When you hear someone like Madonna say, ‘JFK Jr. was the best sex I ever had.’ Do you chuckle at that?” Caught off guard, the 33-year-old—who is currently running for Congress in New York’s 12th District—paused before replying: “I’m running for office.”
He didn’t completely avoid the subject, however, adding with a smile: “All I can say is that I bet she was right.”
The exchange has renewed interest in JFK Jr.’s romantic history. A friend of his previously downplayed the claims, saying: “Madonna was totally a fling,” adding, “Nothing more. Barely a fling at that.”
Biographical accounts suggest the pair met in the 1980s, when Madonna was still married to Sean Penn and JFK Jr. was linked to actress Christina Haag. One biography described their interaction as largely physical, noting: “She came on to him, and it was flattery. She was at the top of her game. He loved her body. It was all about physical attraction; it wasn’t going to be anything beyond that.”
JFK Jr. later went on to date several high-profile figures, including Daryl Hannah, before marrying Carolyn Bessette. The couple’s lives were tragically cut short in 1999 when they died in a plane crash along with Lauren Bessette.
Published 09:30 02 Jun 2026 GMT
A biographer has made an eyebrow-raising claim about John F. Kennedy Jr's manhood after Madonna's recent bedroom confession.
The Queen of Pop stunned fans last week while promoting her upcoming album, Confessions II, when she named the son of former President John F. Kennedy as the best lover she'd ever had.
The confession came during a video created in partnership with Grindr, where Madonna joined playwright Jeremy O. Harris, Bob The Drag Queen, dancer Ivy Mugler, designer Raul Lopez, and Interview magazine's Marcello Gutierrez for an unconventional Q&A.
When Lopez asked: "Who was your best d*** down?," the Vogue hitmaker replied: "I’m only going to name dead people," before covering her mouth and whispering: "John Kennedy Jr."
The room immediately erupted in disbelief. "Shut the **** upppppppp!" the group shouted back.
Lopez then added: "Everyone says his d*** was crazy and he was a good f***."
"Mmm hmm," Madonna confirmed. "You’re the third person I’ve heard say that," Lopez continued.
The pair were linked in the late 1980s while her marriage to actor Sean Penn was nearing its end.
Although details of their relationship remain scarce, people close to the late attorney have offered occasional glimpses into what allegedly happened between them.
According to the 2024 book JFK Jr.: An Intimate Oral Biography by Rosemarie Terenzio and Liz McNeil, the relationship was never particularly serious.
"Madonna was totally a fling," one of Kennedy's close pals said. "Nothing more. Barely a fling at that."
The book claims Kennedy was dating actress Christina Haag when he met Madonna and alleges that she pursued him because "she was at the top of her game".
Authors also claimed: "He loved her body. It was all about physical attraction; it wasn’t going to be anything beyond that."
The renewed attention on Kennedy’s love life comes as interest grows in Ryan Murphy’s series Love Story: John F. Kennedy Jr. & Carolyn Bessette, which premiered earlier this year.
The nine-episode drama, available on Hulu and Disney+, follows the romance, relationship, and marriage of Kennedy and Carolyn Bessette-Kennedy before their deaths.
The show is based on Elizabeth Beller’s book Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy.
While the series attracted plenty of attention, it also faced criticism from people close to the Kennedy family, who questioned its accuracy.
One of the strongest critics was Kennedy’s nephew, Jack Schlossberg.
The 33-year-old spoke on CBS's Sunday Morning after the show's release in February, and said: "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," he continued. "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."
Author Maureen Callahan, who wrote the 2024 book, Ask Not: The Kennedys and the Women They Destroyed, also challenged aspects of Kennedy's portrayal.
One scene in the series shows JFK Jr. discussing intense media scrutiny with his cousin, Anthony Radziwill, inside a locker room. After Radziwill jokes about Kennedy's willingness to expose himself at the gym, Kennedy responds: "Apparently, that’s all I’m good for."
Callahan believes that line was completely out of character. Speaking on her podcast The Nerve With Maureen Callahan, she argued: "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," she said before making an even more shocking claim about his behaviour at the gym.
"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.'s life was cut short in July 1999 when the small aircraft he was piloting crashed into the Atlantic Ocean near Martha's Vineyard, Massachusetts.
His wife, Carolyn Bessette-Kennedy, and her sister, Lauren Bessette, were also on board.
All three died in the crash.
Published 12:02 29 May 2026 GMT
A close friend of John F. Kennedy Jr. has spoken out years before Madonna named him as the best lover she's ever had.
The 67-year-old Queen of Pop has never been one to shy away from a headline, and her latest revelation may be one of her most surprising yet.
While promoting her upcoming album Confessions II, the 'Vogue' hitmaker was asked to name the best lover of her life.
Rather than naming an ex who’s still alive, she narrowed her answer to former flames who have since passed away. Her choice? The son of former President John F. Kennedy.
The confession came during a video created in partnership with Grindr, where Madonna sat down with playwright Jeremy O. Harris, Bob The Drag Queen, dancer Ivy Mugler, designer Raul Lopez, and Interview magazine's Marcello Gutierrez for an unconventional Q&A.
When Lopez bluntly asked: "Who was your best d*** down?," she responded: "I’m only going to name dead people," before covering her mouth and whispering: "John Kennedy Jr." per Page Six.
The admission sparked an immediate reaction from the room. "Shut upppppppp!" the group shouted back.
Lopez also responded: "Everyone says his d*** was crazy and he was a good f***."
"Mmm hmm," she confirmed.
"You’re the third person I’ve heard say that," Lopez then added.
The pair were linked briefly in the late 1980s, and years later, one of Kennedy's close friends offered insight into what allegedly happened between them.
According to JFK Jr.: An Intimate Oral Biography by Rosemarie Terenzio and Liz McNeil, published in 2024, the romance was short-lived.
"Madonna was totally a fling," one of Kennedy's close pals said. "Nothing more. Barely a fling at that."
The book claims the two met while Kennedy was dating actress Christina Haag and Madonna was married to Sean Penn.
The unnamed friend alleged that the 'Hung Up' songstress pursued Kennedy because "she was at the top of her game," and claimed that the relationship was driven by attraction rather than any long-term plans.
"It was all about physical attraction, it wasn’t going to be anything beyond that," the source claimed.
Kennedy Jr. was killed in a plane crash near Martha's Vineyard in July 1999 at the age of 38.
He was piloting a small aircraft carrying his wife, Carolyn Bessette Kennedy, and her sister, Lauren Bessette, when it went down in the Atlantic Ocean off the coast of Massachusetts on July 16, 1999.
All three died in the crash.
Published 10:04 29 May 2026 GMT
Madonna has revealed which of her exes was the most memorable in the bedroom - out of the ones that have since died.
The Queen of Pop, 67, is no stranger to dating some of the most eligible men in Hollywood, including Sean Penn, Tupac Shakur, and Guy Ritchie.
When she was recently asked who came out on top (no pun intended) of the people she'd previously been with, Madonna had one clear answer - at least out of all of her exes that are no longer alive.
During promo for her new album, Confessions On A Dance Floor II, working with the gay dating app Grindr, Madonna made a video with playwright Jeremy O. Harris, Bob The Drag Queen, dancer Ivy Mugler, designer Raul Lopez and ID’s Marcello Gutierrez.
According to Page Six, which viewed the video before release, Lopez asked Madonna: "Who was your best d**k down?"
Madonna then responded: "I’m only going to name dead people," before covering her mouth and whispering: "John Kennedy Jr."
Of course, her naming John F. Kennedy Jr. led to uproar in the room, as Lopez joked: "Everyone says his d**k was crazy and he was a good f**k."
Madonna then confirmed: "Mmm hmm," to which Lopez added: "You’re the third person I’ve heard say that."
JFK Jr and Madonna dated briefly in the late 1980s, with the 2024 book JFK Jr.: An Intimate Oral Biography by RoseMarie Terenzio and Liz McNeil, claiming: "Madonna was totally a fling. Nothing more. Barely a fling at that."
The book alleges that the pair met while Madonna was married to Sean Penn and JFK Jr. was dating actress Christina Haag, and claims Madonna was the one to initiate the flirtation, adding: "and it was flattery — she was at the top of her game."
The source claimed: "[It was] all about physical attraction, it wasn’t going to be anything beyond that."
Kennedy Jr. is also said to have remarked that the 'Papa Don't Preach' singer had "one of the most beautiful bodies he had ever seen."
While Madonna says JFK Jr. was the best sex she ever had, the insider alleged in the book that the pair had never actually had intercourse.
They claimed: "They didn’t have the protection measures and she was very on top of HIV prevention," but instead had "fun in other ways".
The book also claims that several years later, when Penn appeared on the December 1998 cover of JFK Jr.’s George magazine, the two men had dinner together and Kennedy told Penn "he never knew Madonna in the biblical sense."
The full video is set to be available on Grindr’s in-app media hub Grindr Presents, as well as YouTube and Instagram.
Published 10:29 09 Jun 2026 GMT
Madonna has sparked outrage after appearing to simulate a sexual act with a younger man in her new music video.
The 67-year-old musical icon released a 10-minute visual titled Confessions II, to promote her forthcoming album of the same name.
The visual featured the first six songs from the project and includes appearances from many celebrities, including Kate Moss, Benedict Cumberbatch, Odessa A'zion, and Julia Garner, who is set to portray Madonna in an upcoming biopic.
One scene in particular quickly became the talking point of the video.
The scene shows the 'Hung Up' songstress dragging a young man into a toilet stall during a nightclub dance party before the pair engage in what appears to be a highly suggestive encounter.
Madonna is then seen getting down on her knees while another person peers over the top of the cubicle with a look of complete shock.
While it's unclear whether the pair is performing an intentionally provocative dance routine or hinting at something more explicit, the scene immediately sparked debate online.
"Someone make her stop please. I have 2nd hand embarrassment," one disappointed viewer said, while another slammed: "Wow shocking! Can't believe her management company let her put out this video. They must really dislike her."
Meanwhile, others praised the music video concept and the singer's commitment to creating a cinematic experience.
"This project (era) might be one of the best things Madonna has ever done. This film is stacked with dance, Easter eggs, so many great songs and surprise appearances," one fan wrote.
Another added: "Confessions ll film is exactly what we need right now and like the real artist and icon she is Madonna is back with strong visual identity for her new era queen of pop isn’t enough when the name is MADONNA."
The controversial visual arrives just days after the 'Like A Virgin' singer surprised fans with a free performance in New York City's Times Square as she kicked off promotion for her new album, which will be released on July 3.
Thousands of fans turned up after receiving just one day's notice of the event, which was also streamed live on YouTube.
Joined by backup dancers and longtime collaborator DJ Stuart Price, Madonna performed a six-song set featuring tracks from both her upcoming album and its 2005 predecessor, Confessions on a Dance Floor.
Her latest single, 'Love Sensation', was among the songs performed, alongside the album's two other released tracks.
She also treated fans to classic hits, including 'Get Together', 'I Love New York', and 'Hung Up'.
Published 16:03 28 Feb 2023 GMT
Madonna has posted a tribute to her older brother, Anthony Ciccone, who sadly passed away at the age of 66 last week.
The devastating news was first announced by the 64-year-old singer's brother-in-law, musician Joe Henry - who is married to her sister Melanie Ciccone - over the weekend.
Writing a heartbreaking post on Instagram, Henry revealed: "My brother-in-law, Anthony Gerard Ciccone, exited this earthly plane last evening. I’ve known him since I was 15, in the spring of our lives in Michigan so many years now gone."
The tribute continued: "As brother Dave Henry (who took this photograph) notes here, Anthony was a complex character; and god knows: we tangled in moments, as true brothers can. "
Read Henry's tribute below:"But I loved him and understood him better than I was sometimes willing to let on. But trouble fades; and family remains - with hands reached across the table.
"Farewell, then, brother Anthony. I want to think the god your blessed mother (and mine) believed in has her there, waiting to receive you. At least for today, no one shall dissuade me from this vision," the 62-year-old added.
On Monday (February 27), the 'Vogue' hitmaker took to her social media to commemorate her brother by fondly remembering the wisdom he passed down to her, from different religions and his favorite authors to music recommendations.
In the picture - which was uploaded to her Instagram Story - she can be seen smiling while sitting at a crowded table alongside several friends and Anthony.
"Thank you for blowing my mind as a young girl and introducing me to Charlie Parker, Miles Davis, Buddhism, Taoism, Charles Bukowski, Richard Brautigan, Jack Kerouac, expansive thinking outing the box," she captioned the throwback picture.
"You planted many important seeds," she added.
Madonna grew up with Anthony and their six other siblings - Martin, Paula, Melanie, Christopher, Jennifer, and Mario - on the outskirts of Detroit.
According to Page Six, the older sibling became homeless after struggling with alcoholism for years and had two run-ins with the law.
Anthony has also given numerous interviews criticizing his family for their alleged lack of support, saying: "I’m a zero in their eyes - a non-person. I’m an embarrassment," per the outlet.
"If I froze to death, my family probably wouldn’t know or care about it for six months," he said in 2011. "My father would be very happy if I died of hypothermia, then he wouldn’t have to worry about it anymore. He's old-school, he grew up in the depression."
However, the Daily Mail has reported that despite his words against his family, Madonna offered to pay for him to go into a rehab facility and seek treatment - which he ended up doing and completing in 2o17.
Our thoughts are with Anthony's family and friends at this time.
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