“I hope your ol’ plane crashes”: The conversation with Buddy Holly that Waylon Jennings always regretted
Whenever a musician dies, a sudden veil of mystery immediately pulls over their entire legacy as people scramble to figure out if there were any previous indications. Unfortunately for Waylon Jennings, something he said the night before “the day the music died” always haunted him.
There have been countless near-death experiences in music history, but something about Jennings’ experience seems especially poignant, and not just because of the decision that ended up ultimately saving his life. Jennings had been Buddy Holly’s bass player during his Winter Dance Party tour in 1959, joining Holly along with the likes of Ritchie Valens and JP Richardson.
Alongside celebrating the legacies of well-established musicians as well as up-and-coming stars (like Dion and the Belmonts), Holly had reportedly also agreed to the tour for two major reasons. He was quickly losing financial steam and needed a guaranteed fixer (after his previous Crickets manager stole from him), and he also wanted to save the money to move to New York with his pregnant wife.
But what is now fairly romantically deemed “the day the music died” was actually the “tour from hell”, according to historian Bill Griggs, because not only did the musicians quickly burn out due to lack of downtime, they were also harried and worn down by the poor conditions of travelling from one place to another, namely in long, cold bus rides that started to make some people fall ill. There were no road crew, meaning musicians had to haul equipment out themselves, and the buses kept breaking down.
During one particularly harrowing moment, one of the buses broke down, and the musicians had to set some newspapers alight inside the bus to keep themselves warm until help arrived around two hours later. Drummer Carl Bunch even developed frostbite because of the freezing temperatures and had to be taken to the hospital, leaving the others scrambling for a temporary percussionist replacement (the others took turns filling in for him instead).
Evidently at his wits’ end with the stark conditions and the very real threat it was posing to the lives of himself and his accompanying musicians, Holly chartered a plane for their next gig, which would have been in Moorhead, Minnesota. Jennings was originally supposed to join Holly on the flight, but as Richardson had contracted the flu, he offered up his seat to travel by bus instead. A move which unknowingly saved his life.
But it also left him with a memory that would haunt him forever. Before Holly boarded the plane, Holly had teased him with a quip that he’d only meant in jest at the time: “So, you’re not going with us tonight on the plane, huh?” He said. “Well, I hope your ol’ bus freezes up.”
Responding to this playfulness was the one line Jennings would carry with him forever: “Well, I hope your ol’ plane crashes.”
While those fateful words followed Jennings for a long while after, it’s almost stranger to think about the implications of the near-miss itself, and whether Jennings felt any sense of prophecy at having come so frighteningly close to such a historically impactful tragedy. The day the music died is what it’ll always be known as, but could it ever really die if the leftover ghost of it never stopped echoing in the walls of his ruminating mind?
