I Miss John Perry Barlow, and His Wild, Unlikely Friendship With JFK Jr.
Binging the wildly popular new drama Love Story dragged my mind back to a strange, searing week I lived through decades ago. It was April 1994, and I was working from a cramped studio apartment I shared as an office with Cynthia Horner, a psychiatrist who’d recently moved out to live with her boyfriend—my friend John Perry Barlow, a songwriter and pioneering cyberspace philosopher.
Late that afternoon, my wife called me with shocking, out-of-the-blue news: Cynthia was gone, just days shy of her 30th birthday. I got Barlow on the line immediately, and he told me she’d died suddenly mid-flight. Both had caught a brutal flu the week before, and the virus had silently attacked her heart. I dropped everything and headed straight for Barlow’s home. Over the next six hours, Barlow, another friend, and I sat with our senseless loss: we cried, we drank, we blasted music and head-banged, anything to process the shock. That third friend was no random acquaintance. It was John F. Kennedy Jr.
Barlow, who died in 2018 at 70, was famous for so many things. He called himself the Grateful Dead’s junior lyricist, was one of the internet’s earliest and most passionate evangelists, co-founded the Electronic Frontier Foundation, and was an unmatched legendary connector of people. He was also a foundational figure in WIRED’s earliest days. What many also knew was that he was one of the closest friends of the man the public called the American Prince: the son of our assassinated president. Their friendship was no secret—Barlow was an unapologetic name-dropper after all—but the pairing was always fascinating, revealing something raw and true about both men.
Their bond began in the summer of 1977. Barlow was tending his family ranch in Pinedale, Wyoming, when Jackie Kennedy reached out, on the suggestion of a mutual friend. As Barlow recounted in his posthumously published autobiography Mother American Night, Jackie wanted her 17-year-old son JFK Jr. to get a taste of rugged, unpolished working ranch life. Barlow said yes, and balanced out the teen’s daily ranch chores with LSD. While tripping, they took long drives out in Barlow’s pickup and even dropped explosives down abandoned gas wells. The experience forged a tight bond, and over the decades Barlow shifted from a rebellious, rogue father figure to a close, equal friend.
It was a lifelong connection. Barlow wrote about attending a 1993 Prince concert with Kennedy, where the pair tripped again. Kennedy thought the crowd was far too reserved, so he urged Barlow to get up and dance. By the end of the set, Barlow recalled, the entire Radio City Music Hall was dancing right along with them. Later, after Barlow and Cynthia got together, the two couples went on regular double dates: Barlow and Cynthia, Kennedy and his then-girlfriend Daryl Hannah. After that terrible night I spent grieving with the two men, Hannah flew to New York and helped sort through all the messy logistics of planning Cynthia’s memorial. She was, by all accounts, a lovely, warm person.
In 1994, Kennedy moved on from Hannah and began courting the charismatic Carolyn Bessette. Barlow became a confidant to his friend’s new partner, and even took part in the small, intimate wedding ceremony the couple held in 1996. One surviving photo shows Barlow preparing for the formalities alongside JFK Jr., Ted Kennedy, and the officiating priest. I never got to hear what Barlow said to honor the couple, but I’d bet the lyricist who wrote Estimated Prophet delivered sharp, memorable lines that blended perfect comedy and quiet insight.
In Mother American Night, Barlow offered a little-known alternate context for the fatal flight that killed JFK Jr., his wife Carolyn, and her sister. He explained that Kennedy pushed to take off at sunset, ending in a deadly night flight, because he’d only just finished writing a long, heartfelt condolence email to Barlow—Barlow had just announced his own mother’s death to his 2,500 closest friends, and Kennedy wanted to respond properly before traveling. Regardless of the exact reasons for the late takeoff, Barlow shared one warning he’d given Kennedy years earlier that ultimately went unheeded: “When you lose sight of the horizon don’t look for it. Just put your eyes on the instrument and believe it.”
I have one small, strange personal anecdote I’ve never forgotten, from that night we grieved Cynthia, that gives a tiny peek into the wild dynamic between Barlow and Kennedy. We were sitting in our impromptu shiva when my wife called Barlow’s apartment. Kennedy picked up. My wife said, “Is this John?” He said yes, and she began to express her condolences for Cynthia’s death. “No,” he corrected her gently, “It’s John Kennedy.” Then he passed the phone to Barlow, who was sitting on the floor right at Kennedy’s feet. When Barlow got on the line, my wife asked, “John, how are you holding up?”
Barlow snorted. Then he said: “Well aside from that, Mrs. Kennedy, how did you like Dallas?”
It was a reference to an old dark joke, a twist on the classic tasteless gag about Mrs. Lincoln and the play she attended with her husband the night he was assassinated in 1865. But it’s almost certain no one had ever made that crack in front of the assassinated president’s own son. Kennedy looked like he’d been slapped. He stared at Barlow, stunned, a clear what-the-fuck look on his face. Barlow immediately realized his blunder, stared back for a beat, then wrapped his arms around Kennedy’s legs. I watched Kennedy process the moment and cut Barlow slack: the man had just lost the love of his life. The tense, awkward moment passed.
I couldn’t stop thinking about that story as I worked my way through the somber television adaptation of Kennedy and Bessette’s romance that first stirred these old memories. In my opinion, the show could have used a little more of Barlow’s messy, unapologetic energy. To be clear, I’m not here arguing for a rewrite of the series. I just miss Barlow. And just like the rest of the world, I miss Kennedy and Bessette, too.
