February 2nd, 1959: Buddy Holly, Ritchie Valens, and The Big Bopper play their last show as part of the "Winter Dance Party" tour, stopping this night at the Surf Ballroom in Clear Lake, IA. Admission: $1.25. The last song of the night: The Big Bopper's "Chantilly Lace."
February 3rd, 1959: Within minutes of takeoff from the Mason City, IA Airport, at around 1:00 AM CST, the chartered Beech-Craft Bonanza airplane No. N3794N containing Buddy Holly, Ritchie Valens, and The Big Bopper crashes into the Iowa countryside, killing all three in addition to pilot Roger Peterson. The plane, headed for the next "Winter Dance Party" tour stop in Fargo, ND, had been chartered by Holly in order for the band members to travel in heated comfort and to arrive early for their next gig.
When he learned that band member Waylon Jennings, who would eventually become a country star in his own right, had decided to take the freezing bus instead, Holly had joked, "Well, I hope your old bus freezes up." Jennings joked back, "Well, I hope your plane crashes." Another Holly band member, Tommy Allsup, flipped a coin with Valens for the last available seat, losing the coin toss. Valens exclaimed, "That's the first time I've won anything in my life!"
Pilot Peterson, not having been informed of worsening weather conditions, decided to fly "on instruments," meaning without visual confirmation of the horizon, which led to the crash. The tragedy was later immortalized as "The Day The Music Died" by Don McLean in his famous song "American Pie."
February 4th, 1959: Following the tragic plane crash the night before, Frankie Avalon and Jimmy Clanton take over the headlining spots on the "Winter Dance Party" tour.
February 7th, 1959: Buddy Holly's funeral is held at the Tabernacle Baptist Church in Lubbock, TX, drawing over a thousand mourners. Holly's widow does not attend. On the same day, Ritchie Valens is buried in San Fernando Mission Cemetery.