It was a snowy, miserable day in Clear Lake Iowa on February 3rd, 1959. The "Winter Dance Party Tour" had just played the small town north of Des Moines. The tour featured four of the hottest acts in rock and roll, Buddy Holly, Ritchie Valens, Dion DiMucci and J.P. "The Big Bopper" Richardson.

Originally, the trio was supposed to travel to their next destination, Moorehead, MN for a show by bus. Looking at a long ride by bus between Clear Lake and Moorehead, and with horrible weather conditions ahead, Holly decided to charter a plane before the Iowa show, to fly himself and two of his band members to Fargo, North Dakota. Holly's guitar player, Tommy Alsup, lost his seat on the Dwyer Flying Service Beechcraft Bonanza in a coin flip to Valens, while his bass player, Waylon Jennings, offered his seat to Richardson who was suffering from the flu that ravaged those on the tour bus. A fourth seat was offered to DiMucci (lead singer of Dion & The Belmonts), but he declined because he didn't want pay the $36 boarding fee, because it equaled the amount of the rent of his childhood home.

The plane left Mason City Municipal Airport in an eery mix of fog and snow, with gusting winds between 20 & 30 miles per hour. The 21-year old pilot, Roger Peterson, was working on his instrument rating at the time of the flight. He had taken his instrument rating on planes with a different type of altitude indicator than was equipped on the Bonanza. The pilot had failed his instrument checkride just prior to the flight, and the weather forced him to try to fly on instruments he was not familiar with, and at a critical point in the flight.

Unfamiliarity with the instruments led Peterson to believe he was ascending, when in fact the plane was descending. The investigation into the crash also concluded that he had also received inadequate warnings about the weather, which, knowing his own limitations may have led to him postponing the flight.

The plane was reported missing the next morning by the owner of the flight company, Hubert Dwyer, who then went out in his own plane, discovering the crash sight less than six miles from the take off. When the local sheriff reached the crash sight, the bodies of Holly and Valens lay near the plane; Richardson's body was thrown over a fence into a neighboring cornfield, while Peterson's body was entangled in the plane's wreckage. The county coroner Smiley declared that all four had died instantly from "gross trauma" to the brain.

The results of the Civil Aeronautics Board (CAB) investigation concluded that soon after takeoff, Peterson became disoriented due to the unfamiliar way the aircraft's attitude indicator depicted pitch, combined with an inability to find a point of visual reference on a starless night with no visible lights on the ground and the inability to detect the horizon. He lost control of the plane, and the aircraft cartwheeled across a cornfield.

The Bonanza was at a slight downward angle and banked heavily to the right when it struck the ground at around 170 mph. The plane appears to have crumpled and then skidded another 570 feet across the frozen landscape before the broken wreckage came to rest against a wire fence.

Waylon Jennings and Tommy Allsup continued the tour for two more weeks, featuring Jennings as the lead singer. Finally, haunted by his final words to Holly, Jennings left the tour after two weeks. His final conversation with the former Crickets leader took place after Holly found out Jennings had offered up his seat to Richardson. "I hope your bus freezes up", Holly told Jennings in jest. Waylon comically replied, "I hope your plane crashes..." Words that would reportedly haunt Jennings until his death in 2002.

In 1988, Ken Paquette, a Wisconsin fan of the 1950s era, erected a stainless steel monument that depicts a guitar and a set of three records that bear the names of each of the three performers.  A large plasma-cut-steel set of Wayfarer-style glasses, similar to those Holly wore, sits at the access point to the crash site. In February 2009, a new memorial made by Paquette for pilot Roger Peterson was unveiled at the crash site. And road originating near The Surf Ballroom, the site of the trio's final perfomance, extending north and passing to the west of the crash site is now known as Buddy Holly Place.

But the most famous tribute, and the one that gave the tragedy its name of "The Day The Music Died", was the song "American Pie" by Don McLean. The tune went to #1 worldwide in 1971 and spent 4 weeks at the top of the U.S. Singles Chart. It was ranked at #5 by the Recording Industry Association of America's list of the Greatest Songs of the 20th Century.