The Best Books About JFK Jr. And Carolyn Bessette, Ranked By Reviews

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John F. Kennedy Jr.'s romance with Carolyn Bessette has fascinated the world for decades. The son of John F. Kennedy and Jacqueline Kennedy Onassis (aka Jackie O) married his love in 1996 and the spotlight on these two never dulled — even after both tragically died three years later in a plane crash. The world was so captivated by their rollercoaster relationship — which included a secret wedding, marriage counseling, and allegations of drug use — that multiple books have attempted to shed some light on their life together. But some are more highly regarded than others.

Elizabeth Beller's insightful tell-all "Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy" may have inspired FX's limited series "Love Story: John F. Kennedy Jr. & Carolyn Bessette," but it's not considered one of the best books about the high society couple based on Goodreads reviews and ratings. At the time of writing, it has an average score of 3.74 on the book review site, which means it sits well below the average score of other retellings of the couple's tragic love story. Also failing to make the cut? Books written by the twosome's one-time confidants. Bessette's ex, Michael Bergin, told his side of the story in "The Other Man: A Love Story — John F. Kennedy Jr., Carolyn Bessette, and Me" (which has a 3.49 Goodreads average at the time of writing) and "Fairy Tale Interrupted: A Memoir of Life, Love, and Loss" by JFK Jr.'s personal assistant and publicist RoseMarie Terenzio (which averages at 3.83). Thankfully though, there are still a handful of non-fiction books that dive into JFK Jr. and Bessette's relationship rumors and red flags and beyond that have fared much better with readers.

With a rating of 3.93 on Goodreads at the time of writing, "America's Reluctant Prince: The Life of John F. Kennedy Jr." by Steven M. Gillon paints a cohesive portrait of the famed attorney's life. The book delves into every aspect of who Kennedy Jr. was before his untimely death in 1999 — including what the author claims really went down between him and Carolyn Bessette behind closed doors. 

The book has been reviewed more than 1,900 times, but some readers claimed the highly detailed book delved a little too much into John F. Kennedy Jr. and Carolyn Bessette's personal lives in a negative way, with one reviewer writing, "It's hard to believe the info came from close friends — especially the awful portrayal of Carolyn. There was plenty of interesting information, even some unknown facts, but much detail could/should have been left out." Another agreed that Bessette wasn't painted in the best light in the non-fiction offering, though a third commented, "This book offered an insight that was every bit shocking, tragic, and beautiful at the same time."

Breaking into the 4.0-star average or above threshold is Maureen Callahan's "Ask Not: The Kennedys and the Women They Destroyed." It has an overall Goodreads score at the time of writing of 4.09, created from more than 22,000 ratings. This book doesn't only put the microscope on John F. Kennedy Jr.'s romance with Carolyn Bessette, it also shines a light on other women who found themselves inside the Kennedy family circle — including JFK Jr.s' mom, Jackie, and Marilyn Monroe, who reportedly dated JFK and Bobby Kennedy. It looks into how their relationships with members of the most powerful families in American history affected them, making this book ideal for those looking to learn more about the Kennedy women's states of mind (it's also a great 2020s feminist addition for your book club). "Ask Not: The Kennedys and the Women They Destroyed" has mainly positive reviews and was a nominee in the Readers' Favorite History and Biography category at the 2024 Goodreads Choice Awards. 

One reader bluntly stated in their review, "The book shows, over and over again, how the women are either told explicitly or made to think that they know what they are getting with a Kennedy man, and, therefore, deserve the way in which they are treated. The mere idea of being with a Kennedy man makes up for it." Others claimed it leaned a little too much into the gossipy side of the Kennedy dynasty, though another wrote, "A captivating exposé that I haven't been able to stop talking about. At times while reading I was in tears and others filled with anger at what and how these women were used, objectified, and discarded."

"The Kennedy Heirs: John, Caroline, and the New Generation — A Legacy of Triumph and Tragedy" by J. Randy Taraborrelli takes a deep dive into the lives of John F. Kennedy Jr. and his siblings. The non-fiction book is based on interviews with those who knew the family, which includes interesting insights into JFK Jr. and Carolyn Bessette's rollercoaster love story, from their meeting all the way up to their tragic deaths. It has a score of 4.12 on Goodreads from more than 1,600 ratings and offers a more comprehensive overview of life and love in the Kennedy family.

"Taraborrelli intersperses the love story of John and Carolyn with chapters about the other Kennedys. It's a clever way to tell the story of the Kennedys as a whole, while keeping the reader hooked," one reviewer stated. Another reader wrote, "I felt the author came close to a lot of truths that illustrate the love, commitment, and dysfunction in the new (and older) generations of Kennedys." Others noted how the book went into detail about JFK Jr.'s life and relationships but still respected the famous family.

Taking the top spot as the best rated book about JFK Jr. and Carolyn Bessette at the time of writing is "JFK Jr.: An Intimate Oral Biography" by RoseMarie Terenzio and Liz McNeil. Though it's a retelling of his overall life story (so doesn't solely focus on his marriage to Bessette), it still doesn't shy away from sharing in-depth details about their tragic love story. The book has an average score of 4.35 at the time of writing, and over 2,200 ratings on Goodreads, where more than half of reviewers gave the New York Times Bestseller full marks.

One reviewer commended the authors for approaching those who truly knew JFK Jr. to obtain firsthand accounts of his life and relationship with Bessette. Another praised the book for shedding light on how the intense media attention surrounding Bessette and Kennedy Jr. affected her state of mind, and the anger felt over their deaths. "I was pleasantly surprised by the extent of details disclosed, and the book felt respectful, personal, and heartfelt," a third reviewer wrote.

To be considered for our ranking of the best books about John F. Kennedy Jr. and Carolyn Bessette, each book needed to be classified as non-fiction and had to explicitly discuss JFK Jr. and Bessette's relationship in detail (books solely about JFK Jr.'s life outside of his relationships or Bessette's chic and simple style were not considered). Each book also needed to have more than 1,000 ratings on Goodreads.