Howard Stern Remembers J.F.K. Jr. Asking Him to Be on the Cover of George Magazine
For someone who built a career on doing things his own way, Howard Stern has never been particularly fond of playing by traditional media rules — especially when it comes to magazine covers. But in a recent on-air reflection, Stern shared a rare exception: the time he agreed to appear on the cover of George Magazine, all because of John F. Kennedy Jr..
The story offers a revealing glimpse into a moment where celebrity, media, and cultural influence collided in the 1990s — and how even Stern, known for resisting industry expectations, found himself saying yes.
“I Wasn’t Doing Covers… Except This One”
Stern admitted that at the height of his fame, he was highly selective about magazine appearances. In fact, he revealed that he typically only agreed to work with Rolling Stone, a publication long associated with cultural icons and boundary-pushing figures.
“I wasn’t doing a lot of magazine covers by choice,” Stern explained. “I would do Rolling Stone — and that was it.”
That makes his decision to appear on the cover of George Magazine all the more unusual. But as Stern tells it, the invitation came from someone he simply couldn’t refuse.
The John F. Kennedy Jr. Factor
At the time, George Magazine was founded and led by John F. Kennedy Jr., often described as American royalty due to his family legacy and public image. Stern spoke warmly about him, recalling not just his influence, but his personality.
“John was the nicest guy,” Stern said. “Charming, easygoing — just a great presence.”
That personal connection ultimately made the difference. Despite his usual reluctance, Stern agreed to participate in the shoot — even though it came with conditions he would normally reject.
A Colonial Costume… and a Chainsaw
The concept for the cover was far from ordinary. Stern was asked to dress in colonial-era clothing and pose with a chainsaw, in a playful — and somewhat surreal — nod to George Washington and the famous cherry tree legend.
Looking back, Stern couldn’t help but laugh at the absurdity.
“They convinced me to be chopping down a cherry tree with a chainsaw,” he said. “And I’m dressed up in this outfit that George Washington definitely never wore.”
The imagery, he recalled, felt more theatrical than historical — somewhere between royal costume and fantasy character.
“I kind of looked like Louis XIV… or Captain Hook,” he joked.
The Art of Persuasion
Stern also pulled back the curtain on how the shoot came together. According to him, the team used a familiar tactic often reserved for high-profile photo sessions: constant reassurance.
“They kept saying, ‘You look great. This is amazing. This is our best cover,’” Stern recalled.
Caught up in the moment, he found himself fully leaning into the role — even comparing his poses to those of supermodels like Cindy Crawford.
“I’m standing there thinking I look handsome with my chainsaw,” he said.
A Moment Frozen in Time
Though Stern now sees humor in the experience, the story reflects a unique era in media history — when personalities from vastly different worlds came together in unexpected ways.
George Magazine itself was an ambitious attempt to blend politics and pop culture, and Stern’s cover embodied that vision perfectly: bold, unconventional, and impossible to ignore.
For Stern, the memory stands out not because of the costume or the concept, but because of the person behind it.
At the end of the day, it wasn’t about the magazine — it was about saying yes to John F. Kennedy Jr.
