The Heartbreaking Song Waylon Jennings Wrote for His Late Friend and Bandmate, Buddy Holly

Sometimes, the only thing to do with tremendous grief is turn it into a song, which is exactly what Waylon Jennings did with this heartbreaking track he wrote for his late friend and bandmate, Buddy Holly. Before Holly’s plane crashed on the day that Don McLean would immortalize as the “day the music died,” the rock ‘n’ roll star had befriended Jennings and taken him under his wing as both his backing bassist and a songwriting protegé in Jennings’ own right.

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Jennings was supposed to be on the same plane that would lead Holly, Ritchie Valens, and J.P. “The Big Bopper” Richardson to their demise on February 3, 1959. At the last minute, Jennings’ plans changed, and his last words to Holly would haunt him forever.

Waylon Jennings Remembers His Last Words To Buddy Holly

Country legend Waylon Jennings joined Buddy Holly’s band in the late 1950s for a “Winter Dance Party” tour across the Midwest. In true Midwest fashion, the weather was miserable, and the band suffered through frequent bus breakdowns in freezing cold weather. Some bandmates got frostbite. The flu went around the group at least once. Desperate for a change in their accommodations, Holly chartered a plane for some of the musicians to take to the next tour stop. Jennings originally had a seat on the plane, but J.P. “The Big Bopper” Richardson asked if he could take it. He had the flu and, due to his size, couldn’t sleep on the bus. Jennings obliged.

In Falling Stars: Air Crashes That Filled Rock and Roll Heaven, Jennings recalled Holly asking him to get food for the band the night of their flight. “He was leaning back against the wall in a cane-bottom chair, and he was laughing at me. He said, ‘So, you’re not going with us tonight on the plane, huh? Well, I hope your ol’ bus freezes up. It’s 40 below out there, and you’re gonna get awful cold.’ So I said, ‘Well, I hope your ol’ plane crashes.’”

History would show why Jennings would regret those words for years to come. That night, Holly’s plane took off into a blizzard that disoriented the pilot and ultimately led to the fatal crash. The rest of the band having made their destination, Jennings remembered the tour manager asking to speak with him outside in his autobiography. “I knew something was wrong. I turned around to Tommy [Allsup, guitarist]. ‘You go.’ Tommy went outside and came back a moment later. ‘Boys,’ he said, ‘the guys didn’t make it. Their plane crashed.’ I was just numb.”

The Country Star Paid Homage To His Late Friend

Although the grief of his friends’ passing led to Waylon Jennings temporarily stepping back from music, he eventually returned to the industry to create his outlaw country music legacy we know him for today. Jennings was at the peak of his fame in the late 1970s, having made history by making the first platinum country album alongside Willie Nelson, Jessi Colter, and Tompall Glaser, Wanted! The Outlaws. Jennings’ follow-up, Are You Ready for the Country, included a heartbreaking tribute to his late friend, Buddy Holly.

Jennings states his emotions clearly in the touching song. Was it really years ago? It seems like only yesterday, the last time that I saw you laugh at me and fly away. He sings in the chorus, Old friend, we sure have missed you. But you ain’t missed a thing.

Jennings speaks to his late colleague, describing the way music had changed since his death in 1959, but commenting that it always seemed to come back to the early rock ‘n’ roll sounds Holly helped pioneer. He even offers a glimpse into his razzing relationship with Holly, which sparked his plane crash comments in the first place. The stories that they tell make you look like some kind of angel, but we both know you’re mean as hell.

The outlaw country legend continued to honor Holly throughout his career, citing the Crickets founder as a massive influence and incorporating his music into his live performances. People talk about you after all this time, Jennings sings in the final verse. You were many things to many people, but you were a friend of mine.

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