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Howard Stern has opened up about his unexpected friendship with the late Carolyn Bessette, though he has promised not to reveal how they became close.
“I knew the real Carolyn Bessette,” the DJ, 72, revealed The Howard Stern Show on Monday, March 23 (via Rolling Stone). “I won’t say I knew her well, but we had many, many conversations, more than casual conversations. She was very lovely. She was a really nice woman … I don’t want to go into how I knew her, but I knew her. I know enough to keep my mouth shut about that.”
Stern went on, “Some stuff you do have to keep private … But she was very nice to me, very open and talkative. She didn’t give me the nose-up-in-the air kind of thing. I don’t have any juicy, gossipy story.”
The radio legend confirmed he had been watching Love Story — Ryan Murphy’s dramatization of Bessette and John F. Kennedy Jr.’s marriage — during his most recent break from The Howard Stern Show.
Stern also knew Bessette’s late husband JFK Jr., having posed for the cover of Kennedy’s George Magazine in 1996. On Monday’s Stern Show, he revealed why he agreed to do a George photo shoot in an era when he was very selective about doing any magazine covers.
“I would do Rolling Stone and that was the only one,” Stern said. “But when John Kennedy Jr. [asks], who is literally American royalty and the nicest guy in the world … he was a super nice guy. And there was the opportunity that perhaps he’d come on the show.”
Stern revealed that Kennedy even showed up for his cover shoot, which cast him as George Washington in colonial attire. (George frequently had its cover stars dress in costumes from the Revolutionary War era.)
“He actually showed up to the shoot,” Stern remembered. “It’s one of the worst covers I ever did, and I did a lot of bad ones. They convinced me to be chopping down a cherry tree with a chainsaw dressed up in colonel garb. I guess I was supposed to be George Washington, but George Washington didn’t wear this s*** I was wearing. I looked like Paul Revere in drag.”
The Stern Show host added, “John and the photographer did that thing they do to supermodels. They go. ‘Gorgeous, you look great. This is the greatest cover.’ I’m posing while the guy is clicking away, and I’m posing like I’m Cindy Crawford or one of the Hadid sisters. That was before I knew about photo approval. I guess I kind of look like Captain Hook or something.”
In return for shooting the George cover, Kennedy granted The Howard Stern Show a rare interview in 1996, where he candidly discussed his relationship with Bessette. (Bessette and Kennedy got married at the First African Baptist Church on Cumberland Island, Georgia, in September 1996.)
Kennedy, Caroline and her sister Lauren Bessette were all killed in July 1999 when his private plane crashed off the coast of Martha’s Vineyard, Massachusetts.
The trio was en route to John’s cousin Rory Kennedy’s wedding to Mark Bailey at the Kennedy family compound in Hyannis Port when their plan encountered bad weather.
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