February 3, 1959: The Day the Music Died. On this date 67 years ago, a plane crash killed rock and roll pioneer Buddy Holly, “La Bamba” singer Ritchie Valens, J.P. “The Big Bopper” Richardson, and the pilot, Roger Peterson. And though he wasn’t on the plane that night, it was a tragedy that would haunt country music legend Waylon Jennings – and leave him replaying his final joke to Holly – for the rest of his life. Buddy Holly had become one of the biggest artists in the country in the 1950s after opening up for Elvis Presley, shifting his music from country to rock and roll but still managing to get discovered by a Nashville talent scout that helped him land a deal with one of the most powerful labels in the world, Decca Records. He had made multiple appearances on The Ed Sullivan Show and toured all over the world with his band The Crickets. But by 1959, Holly had parted ways with The Crickets and assembled a new band made up of Waylon Jennings on bass, Tommy Allsup on guitar, and Carl Bunch on drums. Holly had met Jennings, who at the time was a DJ for a radio station in Lubbock, in 1958, and had even produced some of his early singles like “Jolie Blon.” But after his split from The Crickets, and with the band’s manager withholding money he had earned during time with the band, Holly found himself having to go back out on the road to earn a living. The result was the Winter Dance Party Tour, which kicked off in Wisconsin on January 23, 1959. And it was brutal. The Winter Dance Party Tour The tour took Holly, along with opening acts Ritchie Valens, The Big Bopper, and Dion and the Belmonts, to 24 midwestern cities in the dead of winter with no days off in between. Travel was difficult as the distance between cities hadn’t been considered when scheduling the tour, and the schedule had them zig-zagging across the midwest rather than moving in any sort of route that made sense. The musicians all traveled together on one bus, which were frequently refurbished school buses that would break down and have to be replaced. The buses often lost heat, once leaving the band stranded in Wisconsin in -40 degree temperatures. Bunch got frostbite so bad on both of his feet that he left the tour, and other musicians on the tour took turns filling in on drums. On February 2, the band rolled in to Clear Lake, Iowa, a city that wasn’t originally on the tour but the site of the Surf Ballroom, which the promoter decided to add to the schedule. The manager of the venue gladly agreed to host the tour, which would then turn around and drive back through two cities in which they had already played to get to a show in Moorhead, Minnesota the next day. See what a pain it was? Chartering A Plane With the brutal conditions finally beginning to take a toll, Holly decided to charter a plane to the next stop, which would allow him to get some rest before the show in Moorhead. The manager of Surf Ballroom called a local airport and found a plane that was to fly to Fargo, North Dakota, near Minnesota, where Holly would meet up with the rest of the band. The plane was a Beechcraft Bonanza with tail number N3794N, which seated three passengers and would be piloted by 21-year old Roger Peterson. It cost $36 per passenger, or the equivalent of $400 per person in 2026. Who Would Get The Two Seats? There’s some debate over who was scheduled to fly on the plane with Holly. Dion and the Belmonts lead singer Dion said that he was offered a spot on the plane, along with Valens and Richardson. The most widely-accepted version of the story, however, is that Holly offered the seats to his two bandmates, Waylon Jennings and Tommy Allsup. But Richardson had reportedly come down with the flu during the tour, and according to his memoir, Waylon: An Autobiography, the future country music legend offered his seat to The Big Bopper instead. For the final seat, Valens asked Allsup if he could join the group on the plane instead, and the two reportedly decided to flip a coin for the final spot on the flight. A local DJ who was hosting the show flipped the coin in the dressing room, and with Valens calling heads, he earned the seat on the plane. Allsup would later recall Valens’ remarks when he won the coin toss: “That’s the first time I’ve ever won anything in my life.” It wouldn’t be the only haunting remarks made that night. “I Hope Your Ol’ Plane Crashes” With the travel arrangements set, Holly joked with Jennings about giving up his seat on the plane, jokingly telling his bass player: “Well, I hope your damned bus freezes up.” Jennings would then make what was at the time a lighthearted joke to his friend, one that would come to haunt him the rest of his life: “Well, I hope your ol’ plane crashes.” Just a few hours later, that’s exactly what happened. The Day the Music Died After the show at Surf Ballroom, the airplane passengers made their way to nearby Mason City Municipal Airport, where a light snow was falling and visibility was limited. The owner of the flying service watched as the plane took off, but eventually saw the taillight begin to slowly descend before disappearing from sight. Just five minutes after takeoff, the pilot failed to make the expected radio contact. But it wasn’t until the following morning that the fate of the plane was discovered: The wreckage of the plane, just six miles from the airport. The bodies of the passengers had been ejected from the plane, which crashed into the ground at approximately 170 mph at a 90-degree nose down angle. Subsequent investigation led investigators to believe that the pilot may have been looking at the wrong instrument, and thought he was climbing when he was really descending. Combined with limited visibility and no visual horizon, the cause of the accident was ruled to be pilot error, combined with the inadequate weather briefing that had been provided to him before takeoff. The Loss Of A Friend & Their Haunting Last Conversation In his book, Waylon opened up about how he carried Buddy’s legacy into his own life and career, and how those lessons propelled him to the forefront of the outlaw country music movement of the 1970’s: “He had a dose of Nashville where they wouldn’t let him sing it the way he heard it and wouldn’t let him play his own guitar parts. Can’t do this, can’t do that. ‘Don’t ever let people tell you you can’t do something,’ he’d say, ‘and never put limits on yourself.’ Years later, I’d be in the studio, and the track would really get in the pocket and feel good, and I’d hear those Nashville producers saying scornfully, ’Man, that sounds like a pop hit.’ And I’d remember Buddy talking to me, telling me they thought he was crazy, as that freezing bus moved down the highway from Green Bay, Wisc., to Clear Lake, Iowa.” Waylon clearly went on to become an iconic legend in his own right, but for years he admitted that he was haunted by his own words on the night of the plane crash – and blamed himself for the crash: “I was so afraid for many years that somebody was going to find out I said that. Somehow I blamed myself. Compounding that was the guilty feeling that I was still alive. I hadn’t contributed anything to the world at that time compared to Buddy. Why would he die and not me? It took a long time to figure that out, and it brought about some big changes in my life — the way I thought about things.” Living With Purpose During an interview on The Vinyl Guide podcast, Waylon’s son Shooter Jennings recalled just how much the death of Buddy Holly affected his dad over the years: “Buddy kind of took him under his wing, took him to New York for the first time and really confided in him, and produced some songs on him and asked him to be in the band when he had a disagreement with the Crickets. Put together a band for that last tour, and they were going to go tour in Europe and my dad was going to open the shows, and that was kinda the plan. But yeah, he was his best friend for years, and then the thing happened. They knew each other back in town and everything, in Lubbock, from when my dad was DJ’ing and he was hanging around the studio.” In fact, Waylon went on to fill in for Buddy at the rest of their shows on the Winter Dance Party Tour, which had to be unimaginably difficult. He was also responsible for getting Buddy’s guitar and amp back to his parents, and he carried all of that sadness for a very long time. Shooter says his dad “never went back” the crash site and venue they were at that night until years later, when he was booked there by mistake: “Crazy, crazy. Can you imagine that? To have just been through that and have to do that. He had to bring Buddy’s guitar and amp back to his parents. He talked about Buddy almost every damn day. But at the same time, I think he had had some release of it at different points. He never went back there, and one time he accidentally got booked there in like 1999. He didn’t realize he was going there until he got there, and it had always been on a list of places he would never go back to. After that, he said he was able to look at the plane wreckage. He had never been able to look at the picture of the wreckage until after that. So I think he kind of came full circle with it later in life. But the whole thing, yeah, it wrecked him for like ten years, then he kinda came back to music.” But possibly the most interesting part of this story was how much Shooter says it “psychologically affected” his dad, because it did become known as “the day music died,” and Waylon felt like “he did it” in a sense after what he said the last time he saw Buddy and part of the band. I think most people would be haunted by that, and he certainly was. Ultimately, though, Waylon knew he couldn’t change any of it, though it “haunted” him to a certain extent forever: “But I think it definitely psychologically affected him. Imagine the whole thing being called ‘the day music died,’ and you did it, you know what I mean? I think he came to terms with it at a young age, too, that he knew he couldn’t change it. But it still haunted him, and I think he felt in a lot of ways that he was on bonus time from that point forward. That he had to kinda live with purpose in a way because he survived.” It’s understandable how much that shaped Waylon’s outlook and career, but it’s really interesting to hear about it from Shooter’s perspective, who was obviously privy to a lot of information that none of us would ever know otherwise. It was a massive tragedy that none of them could have predicted, but that doesn’t change how it affected those surrounding them. The event would come to be known as “The Day the Music Died” after being commemorated by Don McLean in his song “American Pie,” which mourned not only the loss of talent but the cultural changes that resulted from the death of such icons. While it’s a memorable day in music history for everybody, there’s maybe nobody that it affected more than Waylon Jennings – one that would haunt him for the rest of his life.The post “I Hope Your Ol’ Plane Crashes” – The Joke That Would Haunt Waylon Jennings For The Rest Of His Life first appeared on Whiskey Riff.