'Love Story': The Tumultuous Relationship of JFK Jr. and Daryl Hannah | Vanity Fair

Love Story, which premiered on February 12, dives headfirst into the courtship and eventual marriage of John F. Kennedy Jr. and Carolyn Bessette. But before JFK and Jackie O’s son fell for a mysterious Calvin Klein PR maven, he was entangled in another, high-profile, and highly volatile relationship with a beautiful blonde: movie star Daryl Hannah.

According to People, America’s prince and the Blade Runner actor first met in the early 1980s, when their families were both vacationing in the Caribbean on the isle of St. Martin. Years later, in 1988, the pair had another fateful meeting when Kennedy’s aunt, Lee Radziwill, married director Herbert Ross. Ross had recently directed Hannah in Steel Magnolias, set to come out the following year. That chance reencounter kicked off one of the most tumultuous and talked-about relationships of the late 1980s and early 1990s.

When they began dating, Kennedy was in the midst of completing his law degree at NYU—and already a public figure due to his family bona fides. In 1988, he was named People’s fourth-ever Sexiest Man Alive. Meanwhile, Hannah was a rising starlet, breaking through as the violent and acrobatic Pris in Ridley Scott’s 1982 science fiction classic, Blade Runner. Hannah established herself as a versatile actor in hit films like Roxanne (1987) with Steve Martin; Wall Street (1987) with Michael Douglas; and, perhaps her most iconic role, as Madison, a mermaid who falls for Tom Hanks in Ron Howard’s Splash (1984).

As an aspiring lawyer and a famous actor, Kennedy and Hannah may have seemed to have little in common. But according to People, both were outdoorsy, with a fondness for skiing and camping. Kennedy also had acting aspirations of his own, treading the boards often as an undergraduate at Brown University. He even starred in an Off Off Broadway production of Irish playwright Brian Friel’s Winners at the Irish Arts Center in 1985. In Love Story’s first episode, Paul Anthony Kelly’s Kennedy suggests that Jackie O (played by Naomi Watts in the series) didn’t find acting to be a suitable career for her son, and prevented reviewers from attending the run. While there’s no evidence this actually happened, the play only ran for six performances, and he started pursuing law school soon after. You do the math.

Kennedy and Hannah’s relationship captured the attention of both tabloids and the public. The couple was featured on the cover of People in 1993 with the headline “John F. Kennedy Jr. and Daryl Hannah: America’s most eligible bachelor finally meets his match.” “It’s getting really annoying. I get asked about it all the time,” Hannah told Entertainment Weekly that same year of her relationship with Kennedy. “This morning I call up my plumber, and even he asks me. Oh, brother, I’m just trying to get my pipes fixed. Why can’t people talk about something else?”

At the same time, the couple sometimes put on a bit of a show for the crowd. In 1993, a neighbor of the pair—now reportedly living together in Hannah’s apartment on the Upper West Side—told People that she had seen Kennedy and Hannah dancing one night on their rooftop. Hannah was barefoot, wearing a shirt as a nightgown, and Kennedy was clad only in his boxers. “They were doing this little love play,” said the neighbor. “He was tickling her, and she’d run away. Then he’d catch her, and they’d dance around. Even if you didn’t know who they were, you’d be entranced.”

Their relationship “felt fantastical, adventurous,” according to Amelia Barlow, the daughter of Kennedy’s friend John Perry Barlow. In Liz McNeil and RoseMarie Terenzio’s book JFK Jr.: An Intimate Oral Biography, Barlow went so far as to compare Hannah and Kennedy’s relationship to Kennedy’s eventual marriage, calling it “a little bit maybe naive or immature compared to his relationship with Carolyn [Bessette]. There was a little bit more, like, fire—and fight.”

Love Story repeatedly suggests one major source of strife in Kennedy and Hannah’s relationship: Jackie O, who allegedly didn’t approve of her son’s relationship with the actor. JFK Jr: An Intimate Oral Biography suggests the same thing, quoting Kennedy as telling one friend in 1993, “She’s not getting along with my mother, and so I’m living in the basement of one of my friend’s places now.” But according to People, Hannah’s stepmother, Sue Wexler, didn’t agree with that notion. “The stories I’ve heard are just unbelievable,” she said. “Daryl told me [Onassis] has been very warm and affectionate.”

But it wasn’t meant to be. According to An Intimate Oral Biography, Kennedy first met Bessette around 1991 at the Calvin Klein store in Manhattan, where she was working as a sales associate. Despite still being with Hannah at the time, he was instantly smitten. “We were running around Central Park West and we started walking, which was unusual because the guy just wanted to run forever. He said he was completely enchanted by this woman, Carolyn Bessette,” Brian Steel, a close friend of Kennedy who worked with him as a prosecutor in Manhattan’s district attorney’s office, told McNeal and Terenzio. “And I was like, ‘What about Daryl?’ because they were still together, and he is like, ‘I think we’re going to break up.... I met her at Calvin Klein.’”

New York artist Sasha Chermayeff, who was also one of Kennedy’s closest confidantes, also remembers things getting messy once Bessette entered the picture. McNeal and Terenzio quote Chermayeff as she recalls attending a party with Kennedy and spotting Bessette from across the room. “He was still with Daryl,” says Chermayeff. “It was private and I wasn’t going to be like, ‘Oh my God, do you have the hots for her…and what about your relationship?’ John never said anything to me, but he was overlapping with Carolyn while he was with Daryl—I’m convinced that there was quite a bit of overlap.”

Terenzio, who was Kennedy’s executive assistant before overseeing his PR and philanthropic causes and serving as chief of staff at George magazine, has a different version of events. In An Intimate Oral Biography, she writes that while Bessette and Kennedy did meet for the first time in 1991, they didn’t seriously reconnect until 1994. “They had dinner at Provence downtown, and John gave her the impression he was no longer in a relationship with Daryl and he wanted to date her exclusively,” Terenzio writes. In Love Story, Bessette (Sarah Pidgeon) becomes aware that Kennedy might not be as single as he seems after she sees a photo of him and Hannah (Dree Hemingway) attending a wedding together, hand in hand, on the front page of the Daily News. According to Terenzio, that’s not far from what actually happened: “Not long after, there was a picture in the Daily News of John and Daryl holding hands at a movie premiere.” Per Terenzio, he sent Bessette flowers the next day, explaining that he attended the premiere as a friend because Hannah didn’t want to go alone.

Bessette and Kennedy didn’t start officially seeing each other until 1994, the same year Hannah and Kennedy officially ended their five-year relationship. While all breakups are hard, Hannah and Kennedy’s was particularly painful. In May of 1994, Kennedy took Hannah’s dog on a walk in Central Park. During the walk, Kennedy lost control of the leash, and the dog was hit by a car and died. Kennedy was then tasked with transporting the dog’s ashes to Los Angeles. Per a friend quoted in An Intimate Oral Biography, Kennedy used a box “that Daryl didn’t approve of—I think she wanted something gold.”

Real tragedy would soon strike. Jackie O, who had been seriously ill with non-Hodgkin’s lymphoma, took a turn for the worse while Kennedy was in Los Angeles. She died on May 19. According to An Intimate Oral Biography, Carole Radziwill, the journalist and former Real Housewives of New York City star who was married to JFK Jr.’s cousin Anthony Radziwill, had dinner with Kennedy that week in New York. “John felt [Daryl] was punishing him by insisting he fly to LA,” Radziwill is quoted as saying. “It was just a terrible time and a bad omen.”

Hannah and Kennedy called off their relationship shortly after. He’d go on to date Bessette, marrying her in 1996. Hannah married musician Neil Young in 2018. While they had their ups and downs, Hannah and Kennedy’s relationship was ultimately no match for Bessette and Kennedy’s connection. As Chermayeff put it, “I think he was obsessed with Carolyn from the minute he met her.”

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