On this day in 1959, a small plane crashed in Iowa. The Passengers were Buddy Hollie, Richie Valens, The Big Bopper and the plane’s pilot.
The three week Midwest tour was going badly. The bus kept breaking down and the heater did not work, Wikipedia picks up the story:
Following a performance at the Surf Ballroom in Clear Lake, Iowa, on February 2, 1959, Holly chartered a small airplane to take him to the next stop on the tour. He, Valens, Richardson (the Big Bopper) and the pilot were killed en route to Moorhead, Minnesota, when their plane crashed soon after taking off from nearby Mason City in the early morning hours of February 3. Bandmate Waylon Jennings had given up his seat on the plane, causing Holly to jokingly tell Jennings, “I hope your ol’ bus freezes up!” Jennings shot back facetiously, “Well, I hope your ol’ plane crashes!” It was a statement that would haunt Jennings for decades.
In 1972, Don McLean recorded American Pie, a song about the Day the Music Died.