Buddy Holly was touring with Ritchie Valens and The Big Bopper, on a jaunt that was scheduled to hit 25 Midwestern cities in three weeks. Angered by rough bus tours that left band members sick with the flu and one hospitalized with frostbite, Holly decided to charter a plane from Iowa to Minnesota.
The official investigation concluded that a combination of pilot error and poor weather conditions caused pilot Roger Peterson to lose control of the plane and crash.
One of the most famous stories surrounding the crash is that country star Waylon Jennings, a then-new addition to Holly's backing band, surrendered his seat to the Big Bopper and elected to take a bus. According to Waylon Jennings's autobiography, when Holly learned that Jennings was taking a bus instead, he told him, "Well, I hope your ol' freezes up." Jennings responded, "Well, I hope your ol' plane crashes," an ill-fated quip he said haunted him for the rest of his life.
Luck, bad and otherwise, surrounded the flight from the beginning: In Falling Stars: Air Crashes That Filled Rock and Roll Heaven, Rich Everitt says that Valens won his spot on the plane from guitarist Tommy Allsup in a coin toss. (Allsup later started a club called "Tommy's Heads Up Saloon" in Fort Worth, Texas named after the fateful event.)
The first song to memorialize the event was actually Eddie Cochran's "Three Stars," but of course Don McLean's "American Pie" is the song most closely linked to the incident; after all, it's where we got the phrase "the day the music died."