After terminating his partnership with The Crickets, Buddy Holly assembled a new band consisting of Waylon Jennings, Tommy Allsup, and Carl Bunch, to play on the '"Winter Dance Party" tour. The tour also featured rising artists Ritchie Valens and The Big Bopper, who were promoting their own recordings as well. The tour was to cover 24 Midwestern cities in three weeks.
The distance between venues and the conditions prevalent aboard the poorly equipped tour buses adversely affected the performers. Cases of flu spread among the band members, and Carl Bunch was hospitalized due to frostbite. Frustrated by the conditions, Holly decided to charter a plane when they stopped for their performance in the Surf Ballroom in Clear Lake, Iowa, to reach their next venue in Moorhead, Minnesota. Carroll Anderson, owner of the Surf Ballroom, chartered the plane from the Dwyer Flying Service. Richardson, who was affected by the flu, swapped places with Waylon Jennings, taking the latter's place on the plane, while Tommy Allsup lost his place to Ritchie Valens on a coin toss. Dion DiMucci (of Dion and the Belmonts fame) decided not to board the plane for the $36 fee.
The investigation of the incident determined that soon after take off, a combination of poor weather conditions and pilot error caused spatial disorientation that made pilot Roger Peterson lose control of the plane. Hubert Dwyer, owner of the flight service company, could not establish radio contact and reported the aircraft missing the next morning. He took off in his own Cessna 180 and spotted the wreckage less than six miles (9.7 km) northwest of the originating airport in a cornfield. He notified the authorities who dispatched Deputy Bill McGill, who drove to the wreck site and found the bodies of the passengers and pilot. They were later identified by Carroll Anderson.