Waylon Jennings was Forever Haunted by his Last Words to Buddy Holly

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Tony Maples Photography


It’s been six decades since the infamous plane crash that took the lives of Buddy Holly, Ritchie Valens, and J.P. Richardson (better known as “The Big Bopper”). Over time, the living links to that fateful night have diminished – the ones who were present for the twists in destiny that saw this horrid tragedy occur. To some, it was luck of the draw, and to others, it’s a haunting memory. One man, himself a music legend, shared his memory of that night, and it’s evidence of how impactful this moment in time has truly been. He did so prior to his own death, and 17 years later, it epitomizes how a seemingly innocent decision can affect you your entire life.

Country music superstar Waylon Jennings passed away at the age of 64 in 2002. In 1999, he sat down for an interview with “Behind the Music,” a documentary series from VH1. As a friend and former member of Buddy Holly’s band, his interview gave weight to the already heavy subject matter around the final hours of Holly’s life. His final words to the teen idol would haunt him for years to come. A link to that interview was shared on the YouTube channel of Steven Allan Jones, and Jennings’ last words to Holly can be heard below.

Video: YouTube/Steven Allan Jones

The plane took off from Clear Lake, Iowa, on the night of February 2, 1959. It was in weather that was bitterly cold. The plane had been chartered by Holly following poor touring conditions on their bus which had resulted in the hospitalization of one of the band members for frostbite. After their show that night at the Surf Ballroom, there was a coin toss between guitarist Tommy Allsup and rock ‘n’ roll sensation Ritchie Valens for one of the seats onboard. Jennings was also approached by J.P. Richardson (ill with the flu) to see if he would consider giving up his seat on the plane, which Jennings did willingly as a favor to the sick performer. After Holly discovered Allsup and Jennings had agreed to go on with the tour bus, he jokingly remarked to the latter, “Well, I hope your ol’ bus freezes up!” It was then that Jennings replied, “Well, I hope your ol’ plane crashes!”—a remark that would haunt him for decades.

In the interview with “Behind the Music,” Jennings revealed the painful grief he felt following the deadly plane crash. “God Almighty, for years I thought I caused it,” he said. “I was just trying to figure out what to do with myself, you know? I was a completely changed person. I quit for a while—I wouldn’t even play a guitar, I wouldn’t pick it up,” he explained. Thank goodness, he found his way back to Texas, his talent, and his love of music. Jennings originally made a move to Arizona where he was able to process his grief and go forward with a new brand of music. He started his own band called The Waylors, which marked the moment in time that his outlaw country career started and his legacy in the genre was firmly established. The burden of personal grief and constant retrospect that those final words to Holly would have on Jennings is unimaginable to many of us, but his sharing of the memory was most likely a great moment in the relief of that burden. There’s no doubt, his fans and those of Holly’s would agree, the pair most likely had a happy reunion when Jennings passed on 43 years after the crash.