Buddy Holly, tired of the tour bus's broken heater, chartered a small plane to reach the next show in Fargo. Shortly after takeoff from Mason City, Iowa, the pilot, disoriented in a snowstorm and not certified for instrument flying, flew the plane into the ground. All four aboard died instantly. Don McLean later immortalized the tragedy as "the day the music died" in his 1971 song "American Pie."
Buddy Holly was only 22 but already a rock-and-roll pioneer, having written and produced his own hits with the Crickets, a rarity for the era. Frustrated by a freezing, unreliable tour bus during the grueling "Winter Dance Party" tour through the Midwest, he arranged a four-seat Beechcraft Bonanza to fly ahead to the next stop in Fargo, North Dakota, so he could do laundry and get some sleep.
Ritchie Valens, 17, won his seat on a coin flip against Holly's bandmate Tommy Allsup. The Big Bopper, suffering from the flu, swapped his bus seat for Waylon Jennings's spot on the plane; Jennings later said Holly joked he hoped the bus froze, to which Jennings replied he hoped the plane crashed — a exchange that haunted him for decades.
Pilot Roger Peterson, only 21, took off just after midnight into deteriorating weather despite lacking certification to fly by instruments alone. The plane climbed briefly, then plunged into a frozen cornfield five miles from the airport, killing all aboard instantly. The wreckage wasn't found until dawn. The crash ended one of rock's most promising careers before it truly began.