See the Love Story Cast vs. the Real People They Play

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Let’s be real, stepping into the shoes of John F. Kennedy Jr. and Carolyn Bessette-Kennedy? That’s a lot of pressure! It’s hard to imagine anyone feeling comfortable trying to live up to their legacy and the image the world had of them. It’s a truly daunting thought.

For Paul Anthony Kelly, who plays John F. Kennedy Jr. in Hulu’s new series Love Story: John F. Kennedy Jr. & Carolyn Bessette, the role was an incredible opportunity and one he approached with great seriousness.

The actor, who was born in Canada, recently told Harper’s Bazaar that the role felt like a perfect fit. He felt a strong connection to the character, saying he still understands the person at their heart and believes they share similar values. He was confident he could bring something special to the part and enjoy the process.

Though he’s often praised for his good looks, reminiscent of JFK, the 37-year-old actor said playing the role was difficult. He found many personal connections to the character, which helped him create an authentic portrayal, but he’s still surprised it was him who played the part and is still reflecting on the experience.

This drama series creatively reimagines the romance between John F. Kennedy Jr. and Carolyn Bessette, from their first meeting to their wedding. It also depicts the tragic events of July 16, 1999, when the small plane John was flying crashed into the Atlantic Ocean while en route to Martha’s Vineyard, resulting in their deaths.

Pidgeon explained she aimed to accurately portray Carolyn in her performance. She also praised the show’s writers for creating a compelling and nuanced depiction of the private woman behind the public image of the fashion PR executive.

Pidgeon told Harper’s that Connor Hines, the creator and writer, developed a remarkably well-crafted character. She noted that even the limited scenes she initially read for her audition showcased this quality. While she knew of Carolyn Bessette beforehand, she realized she had only scratched the surface of understanding her life and story.

Beyond just John F. Kennedy Jr. and Carolyn Bessette-Kennedy, the film Love Story explores how their friends and family affected their famous relationship. The movie features well-known actors portraying people from their lives, including John’s former partner Daryl Hannah (played by Dree Hemingway) and his mother, Jacqueline Kennedy Onassis (portrayed by Naomi Watts), offering a look at the real individuals who witnessed their romance and its tragic turn.

Keep reading for a closer look at how the cast of Love Story transformed into their TV characters.

New episodes of Love Story drop Thursdays on Hulu.

Canadian model and actor Paul Anthony Kelly seemed perfectly cast as the Prince of Camelot, a role that felt natural given his striking looks and full head of hair. The role carried a poignant weight, as it portrayed a man tragically killed in a 1999 plane crash along with his wife, Carolyn Bessette Kennedy, and her sister, Lauren Bessette.

The show’s creators meticulously recreated the ’90s wardrobe and style of the fashion icon, who famously worked with designer Calvin Klein. But actress Sarah Pidgeon focused on capturing more than just the star’s outward appearance during filming – she delved deeper into who she was as a person.

Sarah shared with TopMob News at The Actor Awards on March 1, 2026, how much she enjoyed learning about the character Carolyn while preparing for the show. She added that it was a privilege to portray such a strong and funny woman, and she felt lucky to connect with Carolyn on a deep level while playing her.

Naomi Watts dyed her hair brown to play Jacqueline Kennedy Onassis in a new role. It’s well-known that Jacqueline Kennedy Onassis didn’t approve of her son John F. Kennedy Jr.’s relationship with actress Daryl Hannah.

This isn’t the first time the Australian actress has taken on the role of a real person. She previously played Princess Diana in the 2013 film Diana and recently starred as Babe Paley in Ryan Murphy’s Feud.

Oh my gosh, Dree Hemingway was perfect as that girl from Splash! It’s like, she didn’t even need to transform much, she just was her. And it’s so wild to think about, because that’s the woman JFK Jr. was falling for before Carolyn Bessette-Kennedy! I read all about it – he was kind of dating both of them on and off around 1992. It’s just…fascinating. Dree really captured that whole vibe, you know?

Daryl and John-John had an on-again, off-again relationship for several years after they first met in 1988, but he eventually ended it in 1996 when he married Carolyn.

When Dree landed the role, she contacted Uma Thurman, sending a heartfelt message to The Hollywood Reporter expressing her admiration for Thurman as both a woman and an actress, and stating how much of an honor it was to work on the project. Unfortunately, she didn’t receive a response from Daryl.

Sydney Lemmon played the role of Lauren, Carolyn’s sister and close friend, who was with her and John-John on the plane when it crashed.

Lemmon has previously appeared on TV series like Succession, The Good Fight and Fear the Walking Dead.

Grace Gummer (Meryl Streep‘s daughter) took on the role of Caroline Kennedy, JFK Jr.’s sister. 

She told L’Officiel that the Kennedys were the last American family we truly looked up to like royalty. She has enormous respect for Jackie Kennedy Onassis as a mother, writer, diplomat, lawyer, sister, wife, and daughter, and is deeply impressed by everything she overcame and accomplished.

As a lifestyle enthusiast, I’ve always been fascinated by the Kennedy family and the people around them. It’s incredible how much actor Alessandro Nivola, who you might recognize from ‘The Brutalist,’ resembles the American designer who was Carolyn Bessette-Kennedy’s boss. Honestly, seeing photos of them side-by-side, it’s almost uncanny! And fun fact – Alessandro is also the father of Sam Nivola, who you probably know from ‘The White Lotus.’ It’s a small world, isn’t it?

Carolyn was the primary salesperson for Calvin Klein’s famous customers, such as Annette Bening, Diane Sawyer, and Blaire Trump.

Actress Leila George, who is Australian-American, perfectly captured the appearance of Kelly Klein, the second wife of Calvin Klein. Kelly and Calvin divorced in 1996, after she had become close friends with Carolyn Bessette-Kennedy during her relationship with John F. Kennedy.

Omari K. Chancellor, who plays Elsbeth, portrays Gordon Henderson, a fashion designer and close friend of Carolyn’s. They worked and lived together at Calvin Klein.

The role of Carolyn and Lauren’s mother Ann Messina Freeman landed on UnREAL alum Constance Zimmer.

Constance shared on Instagram in November 2025 that playing Ann Messina Freeman was the most emotionally rewarding, yet heartbreaking, role of her career. She said the entire project – from the story itself to the people she worked with – deeply touched her, and she’s incredibly thankful to have been involved.

Jessica Harper portrays Ethel Kennedy, Robert F. Kennedy’s wife and a dedicated champion of human rights.

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2026-03-06 02:17