
By all accounts, conditions on the tour were brutal and people were getting sick from the freezing Midwestern conditions. The bus was unheated and broke down frequently (via Biography). When the tour made its way into Iowa, Buddy Holly was over it and decided to charter a plane that would take him and his tour mates to Fargo, North Dakota (their next show was in nearby Moorhead, Minnesota). As the plane was rather small, they had to figure out who would fly and who would continue the miserable journey on the bus (per All That's Interesting). In the end, Holly, Ritchie Valens, and J.P. "The Big Bopper" Richardson boarded the ill-fated flight.
According to History, Valens and another guitarist flipped a coin to see who would get a seat. Moreover, Richardson was suffering from the flu and convinced Waylon Jennings, then Holly's band member, to give up his seat for him. In a remark that would haunt him for the rest of his life, Jennings jokingly told Holly he hoped his plan would crash after Holly commented that he hoped the bus would freeze.
After a successful show at the Surf Ballroom, the trio headed to the nearby Mason City airport and departed before 1 a.m. The plane crashed a few miles after takeoff. Holly, Valens, Richardson, and their young pilot, all died. The three singers had been ejected from the aircraft, and Holly's body was found 20 feet away from the wreck. It was later determined that poor weather conditions and pilot error were to blame.
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