When John F. Kennedy Jr. couldn’t convince Madonna to pose as Marylin Monroe for the September 1996 issue of George, he picked Drew Barrymore to dress up as his father’s reported mistress.
It was at that iconic moment when Monroe famously serenaded the patriarch 10 days before his 45th birthday at Madison Square Garden a breathy “Happy Birthday, Mr. President” in front of 15,000 people. The platinum blonde, who was a special guest at the Democratic Party fundraiser, wore a flesh-toned cocktail dress adorned with sparkles, creating the illusion she was nude. Since then, many have speculated the two had an affair.
Elizabeth Mitchell, the former executive editor of George, told Esquire Kennedy never believed anything occurred between the president and the showgirl.
“He just thought it was sort of tweaking the expectations of the public,” she explained.
But by then, Kennedy was accustomed to shocking readers with George. For the October/November 1995 issue, he wanted an all-American celebrity to represent the brand. When he suggested Bill Clinton, it was fashion photographer Herb Ritts who proposed supermodel Cindy Crawford as a more desirable candidate. At the time, Crawford was the host of MTV’s “House of Style.”
Kennedy’s girlfriend Carolyn Bessette, whom he married in September 1996, thought the choice was a no-brainer.
“Cindy Crawford’s perfect,” said Bessette. “She’s all-American, a self-made woman, sexy, strong, and smart.”
Kennedy agreed and called Crawford personally to offer her the chance to appear on the very first cover. Crawford told the magazine, “He reached out directly. And who’s going to say no?”
To keep up with an American theme, Esquire shared Ritts suggested dressing Crawford as George Washington. After studying an old painting of the founding father during the photo shoot, the team stuffed Crawford’s skintight breeches with a sock.
Kennedy, who wasn’t on set, may have been adventurous with his ideas, but even he wasn’t prepared for the grand unveiling. When he saw proofs a few days later, Kennedy told George’s creative director, “Maestro, what the f---?”
The bulge was airbrushed out.
As George took off, Kennedy remained hands-on in fusing politics and pop culture for his magazine. And while he developed a bond with his team, he did keep some secrets — like the time he and Bessette tied the knot.
Fearing the press would get wind of it, his assistant and close friend RoseMarie Terenzio told the staff Kennedy and Bessette were jetting off to Ireland for a vacation and wouldn’t be reachable for a couple of days. Instead, the couple said “I do” on Georgia’s Cumberland Island.
After the ceremony, Kennedy arranged for Terenzio to leave cigars on the male staffers’ desks and Champagne for the women with a note that read: “I just wanted to let you know while you were all toiling away, I went and got myself married. I had to be a bit sneaky for reasons that by now are obvious. I wanted you all to enjoy these small tokens of gratitude and fellowship. You folks all do amazing work and it’s an honor to have you as colleagues.”
According to Esquire, Kennedy’s colleagues described Kennedy as “kind, funny, and easygoing” despite the media scrutiny that followed him throughout his life.
“He was quick to crack a joke, the first to call to congratulate former staffers on new jobs, and in spite of the paparazzi who constantly trailed him, his preferred mode of transportation around Manhattan remained his bike,” described the publication. “The closest anyone comes to a criticism is the observation by a colleague that Kennedy could have a temper — though, they say, he readily admitted mistakes and apologized.”
Toward the end of his life, Kennedy was preparing to shock readers once more by conducting a sit-down interview with Fidel Castro in Cuba. That interview never happened.
This July will mark 20 years since Kennedy, his wife Carolyn Bessette and sister-in-law Lauren Bessette died in 1999 after the aircraft he was piloting crashed into the Atlantic Ocean off Martha’s Vineyard in Massachusetts. The trio was on their way to Rory Kennedy’s wedding. He was 38.
George magazine shuttered in 2001.
Back in 2017, Terenzio told Fox News Bessette was stressed by her husband’s non-stop schedule with George, along with the growing attention from pestering paparazzi when she decided not to attend the family wedding. Instead, she was hoping to take a break. Terenzio said she convinced Bessette to attend and avoid questions being raised on any reported marital woes the tabloids were clinging onto. Bessette would go on that fatal flight, which haunted Terenzio for years.
“It was very difficult,” Terenzio admitted. “It took time for me to get back up and figure out what I wanted to do next… there was a lot of trial and error.”
Terenzio chronicled her memories with Kennedy in the 2012 memoir “Fairy Tale Interrupted,” which helped her cope. Today she is the founder of a publicity firm. And while Terenzio’s career continues to flourish, she still thinks of her friends and what could have been.
“I don’t think he felt any pressure or felt any burden [to pursue politics] because of his name,” she said at the time. “I think he saw it as a wealth of opportunity. And that he was very lucky. He thought about it. He certainly talked about running for office, but his priority was to make George a success.”