The fateful 1959 plane crash that killed Buddy Holly, Richie Valens and The Big Bopper is a far more strange story than most realize. Country Western legend Waylon Jennings also played a very big role in this terrible story, and nearly became a victim as well. Yet as a survivor, he had a lifetime regret because of something he said only moments before that crash. Reportedly, Waylon Jennings just never completely got over his own personal connection to this terrible accident.
Singer-song writer Don McLean once had a huge #1 epic single singing about this terrible event, yet few persons today know about the unfortunate chain of events that led up that February 3, 1959 plane crash that killed three of the greatest rock and roll pioneers of that time.
Buddy Holly, Richie Valens and J.P. "The Big Bopper" Richardson were all hot acts in the early rock and roll music scene. And wise promoters had the three taking part in a very grueling 24 city Winter Midwest concert tour, but the tour bus was being badly stressed due to traveling long distances in very cold weather, and at some point the heater core must have failed in the bus, making travel very cold through the frigid Midwest Winter weather. Eventually, the bus suffered some sort of mechanical failure and stopped running and broke down , where one of Buddy Holly's musicians needed to be hospitalized due to frostbite problems with his feet. The bus was repaired, however the heater core couldn't be immediately repaired for the 380 mile trip to the next concert tour spot in Minnesota, so arrangements were made to fly Buddy Holly, Waylon Jennings and Richie Valens to the next concert tour city for $36 each on a charter plane while the other band members were forced to make the miserable 380 mile trip in the cold tour bus. But, as fate would have it, J.P. "The Big Bopper" Richardson developed the flu and didn't feel very well and asked if Waylon Jennings, who played guitar for Buddy Holly, if he would mind giving up his seat on the small chartered aircraft.
All of these building problems with this ill-fated concert only led to some dark humor jokes between Buddy Holly and his friend, Waylon Jennings. Holly joked about something to the effect of, "I hope your bus breaks down", while Jennings joked that he "hoped" that the plane would "crash". It was a joke that Waylon Jennings would soon to regret. Jennings was unaware that the illness of "The Big Bopper" was something that was soon to save his own life, while his dark little joke about hoping for the plane to crash was now like a dark cloud curse hanging over the flight.
Shortly after the small charter plane left the air, with a 21 year old pilot who wasn't fully experienced must have encountered some weather related spatial disorientation and somehow ended slamming the small plane into the ground near clear Lake, Iowa at around 170mph where the bodies of Buddy Holly, Richie Valens and The Big Bopper were all thrown free from the small plane's wreckage. Only the body of the pilot was still in the wreckage, discovered a short time after the plane lost contact with the airport it took off from.
But, Waylon Jennings was forever marked with both sadness and regret about this terrible tragedy. His little joke about the hoping the plane would "crash" always haunted him for the rest of his life and became a great personal burden for him to carry around.