Special thanks to ThisDayinMusic.com.

Buddy Holly joined the The Winter Dance Party tour, in the winter of ’58, for the cash. The Crickets had broken apart; he’d left his record company and was newly married with a baby on the way. To pay the bills, he was touring with a new band of Tommy Allsup on guitar, Waylon Jennings on bass and Carl Brunch on drums.

The headliners were Holly, Ritchie Valens and The Big Bopper (a.k.a. J.P Richardson). It was a tough and relentless tour in a harsh Midwest winter. The tour bus wasn’t heated and broke down continually. Holly’s drummer even suffered form frostbite at one point. Most of the musicians were ill with colds and flu.

On this day in 1959, Holly, Valens and The Big Bopper played the Surf Ballroom in Clear Lake, Iowa. Tickets were $1.25.

The evening closed with The Big Bopper doing his mega-hit “Chantilly Lace.” And then it was to outside to the bus.

The night was freezing again and Holly; sick of the rickety old bus they were travelling on dipped into his pocket to charter a plane to travel to their next gig in Moorhead, Minnesota. The plane would fly them to Fargo, North Dakota, the nearest airport to Moorhead. He had two open seats on the plane that he offered for $36 each. Dion didn’t want to pay. Jennings fancied flying but gave his seat to Richardson, since he was ill. Allsup was supposed to be on the plane hut flipped a coin with Valens for the seat. Valens guessed right and joined the flight.

Holly, pleased to be escaping the bus, was in a joking mood when he engaged in some lighthearted banter with Jennings. “Well, I hope your old bus freezes up again,” he said. Jennings returned with, “Well, hell, I hope your old plane crashes.”

Little did he know. At around 1 a.m. the chartered plane took off in a blizzard crashing in a cornfield a few miles north of Mason City, Iowa. Holly, Valens, Richardson and the pilot, Roger Peterson, died in the crash.

The crash was discovered the next morning at 9:30 a.m. The coroner’s report makes for some disturbing reading: “The body of Charles H. Holley was clothed in an outer jacket of yellow leather-like material in which four seams in the back were split almost full length. The skull was split medially in the forehead and this extended into the vertex region. Approximately half the brain tissue was absent. There was bleeding from both ears, and the face showed multiple lacerations. The consistency of the chest was soft due to extensive crushing injury to the bony structure.[...] Both thighs and legs showed multiple fractures.”

The Moorhead venue insisted that a show go ahead that night and booked a local kid, the 15-year-old Bobby Vee. Jennings would never overcome the trauma and guilt, but became a country music legend. Dion, who couldn’t afford a plane ticket, became a rock and roll great.

Valens and The Big Bopper would be immortalized by the tragedy, while Buddy Holly is still revered as one of the greatest-ever talents in popular music. As Paul McCartney, someone who knows a thing or two about a good tune, once remarked: “At least the first 40 [Beatles] songs we wrote were Buddy Holly-influenced.”