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."