How the cast of 'Love Story: John F. Kennedy Jr. & Carolyn Bessette' compare to the real people they're playing

By Gabbi Shaw

Nicknamed John-John by the press, Kennedy was unable to miss if you were keeping up with the news in the '90s.

Between his high-profile relationships with stars such as Daryl Hannah and Madonna, his prestigious job at the Manhattan DA's office, and his undeniable heartthrob status, Kennedy was perhaps the most eligible bachelor of the decade.

That is, until he settled down with his future wife, Carolyn Bessette, in 1994.

In the show, Kennedy is played by Paul Anthony Kelly, a model turned actor whose first major role is this show. "I was kind of thrust into this position with no time to think about anything else," he told GQ.

According to the show, Bessette met Kennedy at a party sometime in the early '90s, when he was still involved with Daryl Hannah. In real life, they're actually understood to have met in a VIP fitting room at Calvin Klein, where Bessette helped Kennedy pick out items for his wardrobe, per Elizabeth Beller's book, "Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy."

By 1996, the two had figured it out and were wed in Georgia.

Their relationship was tabloid fodder of the highest degree, with PDA, explosive fights, and playful moments all documented by the paparazzi.

You might recognize Pidgeon from her roles in the 2025 reboot of "I Know What You Did Last Summer," the Prime Video series "The Wilds," or the Tony-winning play "Stereophonic." Pidgeon was nominated for an acting Tony for her performance.

Affectionately known as Jackie O., the former first lady had been living in New York City for decades by the time "Love Story" picks up with the Kennedys. Her second husband, Aristotle Onassis, had died, and she had begun living with her final partner, Maurice Tempelsman.

Onassis died in 1994 due to non-Hodgkin lymphoma.

Watts is best known for her roles in "Mulholland Drive," "The Impossible," and a slew of other Ryan Murphy productions, including "All's Fair" and "Feud: Capote vs. The Swans."

Gummer, one of Meryl Streep's daughters, is no stranger to growing up in the public eye with famous parents.

At the time of the show's beginning in 1993, Bouvier Kennedy had been married to Edwin Schlossberg for seven years, and the two had three children, including Jack Schlossberg.

Gummer may be familiar to fans of "American Horror Story," "Mr. Robot," or "Dr. Death."

Bessette begins the show working at the flagship Calvin Klein store in Manhattan, though across the show's first three episodes, we see her rise up the ranks to become the head of the store's publicity.

The designer himself plays a major role in the series, as he's the person who introduces Bessette and Kennedy at a party, prophetically telling her that she'd thank him for this one day.

The '90s were a busy time for Klein (both the man and the brand). The famous Mark Wahlberg underwear ad was released in 1992, and the discovery of Kate Moss that same year solidified Klein's chokehold on the decade.

In "Love Story," Klein is played by Alessandro Nivola, who you might recognize from "Kraven the Hunter," "The Many Saints of Newark," or "The Brutalist."

Kelly Klein was a respected socialite photographer in the '90s — the launch party for her book, "Poolside," is a major event in episode two, even if the show claims that she didn't do the photographing as much as "curating" the photos.

George is another classic Murphy nepo baby; she's the daughter of Vincent D'Onofrio and Greta Scacchi. She also starred in the TV series "Animal Kingdom."

Radziwill, the son of Lee Radziwill (Jackie O's sister) and Stanisław Albrecht Radziwill, pops up throughout the first couple of episodes as a sounding board for Kennedy.

The two were just over a year apart and were quite close, with Radziwill serving as best man at his cousin's wedding.

Radziwill died from cancer less than a month after the plane crash that took Kennedy and Bessette's lives.

Bergen might be recognizable to fans of "Madam Secretary."

Hannah and Kennedy dated for five years before breaking up in 1994, per People. At the time, Hannah was best known for her roles in "Splash," "Blade Runner," "Wall Street," and "Steel Magnolias."

And you might've guessed — yes, Dree Hemingway is related to Ernest Hemingway; he's her maternal great-grandfather.

In the second episode, Calvin Klein is facing an issue: Their latest star, Mark Wahlberg, was allegedly caught being homophobic to a member of Madonna's entourage, and his face was plastered all over the city. (During a 1993 interview with the Boston Globe, Wahlberg said he had "no hate toward gays.")

Bessette comes to the rescue by recommending swapping Wahlberg for her friend (and sometimes lover) Michael Bergin, a model in his own right.

Bergin became famous after starring in his own underwear ad. In 2004, he published a memoir about his relationship with Bessette, "The Other Man: John F. Kennedy Jr., Carolyn Bessette, and Me."

This is Fearnley's first major role.

Henderson was part of Bessette's extended friend group and is still a successful designer.

"No matter what, we'd still be friends," Henderson told Town and Country in 2025, of what his relationship would've been like with Bessette if she were still alive.

Chancellor has appeared in a few things over the years, perhaps most prominently in the Zac Efron film "The Greatest Beer Run Ever."

Rodriguez also worked at Calvin Klein while Bessette was there, but his real claim to fame was designing Bessette's iconic wedding dress, the understated, chic slip dress that can still be found on wedding Pinterest boards the world over.

He's played by Tonatiuh, who recently had a breakout role in the musical film "The Kiss of the Spider Woman."

To show how easily Bessette could connect with A-listers like Bening, there's a scene in the first episode where the "20th Century Women" actor comes into Calvin Klein for a fitting for a dress to wear to the premiere of "Bugsy."

When she doesn't love the dress, it's Bessette who comes up with the solution of adding an oversize blazer, impressing Klein.

Channell starred in the Prime Video series "Hunters."

You might not know that for the last 15 or so years of her life, Onassis Kennedy spent her time with Tempelsman, a diamond magnate and financier born in Belgium.

You might also not know that he was legally married to someone else the entire time, even though the two were separated.

Tempelsman died in 2025; he was three days shy of his 96th birthday.

In the show, he's played by Adam Grupper, predominantly a theater actor.