Unforgettable Night of Grief: John Perry Barlow, JFK Jr., and a Bond That Transcended Tragedy

As I reflect on my past, a peculiar week in April 1994 keeps resurfacing. I was working from a studio apartment that I shared with Cynthia Horner, a psychiatrist who had recently moved out to live with her boyfriend, John Perry Barlow – a friend of mine and the self-described junior lyricist of the Grateful Dead. The news that Cynthia had passed away suddenly on a plane, just shy of her 30th birthday, left me reeling. My wife called me with the shocking news, and I immediately reached out to Barlow, who was devastated by the loss.

For the next six hours, Barlow and I cried, drank, and head-banged in grief, accompanied by another friend – John F. Kennedy Jr., no stranger to tragedy himself. This peculiar bond between Barlow and JFK Jr. began in 1977 when Jackie Kennedy called Barlow at his family ranch in Pinedale, Wyoming, suggesting that her 17-year-old son spend some time getting a taste of rugged ranch life. The two became close, with Barlow even introducing JFK Jr. to LSD. Over the years, their friendship evolved from a reprobate father figure to a deep and meaningful connection.

In 1993, I spent an unforgettable night with Barlow and Kennedy at a Prince concert, where both were tripping. Kennedy felt that the audience was too restrained, and he urged Barlow to get up and dance – which we did, along with the entire Radio City Music Hall. Later, after Cynthia’s passing, JFK Jr.’s then-girlfriend, Daryl Hannah, flew to New York to help plan a memorial service for her.

In 1996, Kennedy married Carolyn Bessette, and Barlow became part of the intimate ceremony, even preparing for the formalities with JFK Jr., Ted Kennedy, and the priest. I can only imagine the poignant words that Barlow, known for his lyrical prose, delivered to honor the couple.

In his posthumously published autobiography, “Mother American Night,” Barlow provides an alternate explanation for JFK Jr.’s fatal flight. According to Barlow, he had just sent his 2,500 closest friends the news that his mother had died, and Kennedy was late to the airport because he was composing a condolence email to Barlow. Barlow claims he had previously warned Kennedy about losing sight of the horizon – advice that ultimately went unheeded.

One more anecdote from our impromptu shiva stands out in my mind. As we mourned Cynthia’s passing, my wife called Barlow’s apartment, and JFK Jr. answered the phone. When she expressed her condolences, he corrected her, saying it was “John Kennedy.” He handed the phone to Barlow, who was sitting on the floor at his feet. When Barlow took the phone, my wife asked him how he was doing. His response – a snarky reference to an old joke about Mrs. Lincoln and the play she attended with her husband in 1865 – left JFK Jr. stunned.

The moment passed, and I couldn’t help but recall this bizarre episode as I reflect on the strange and wonderful bond between John Perry Barlow, JFK Jr., and a night that none of us will ever forget.

Analysis based on: https://www.wired.com/story/jfk-jr-john-perry-barlow-friendship-love-story/