Blender has this article on the 10 Worst Rock Star Plane Crashes.
On number 10 is Buddy Holly:
Holly, Valens and Richardson were barnstorming through the Midwest in 1959 on a package tour and looking to avoid a frigid February ride from Iowa to Minnesota aboard a bus whose heater was on the blink. Holly chartered a plane for himself and two bandmates, but guitarist Tommy Allsup lost a coin flip to Valens for one seat on the plane, and Holly’s bass player, future country star Waylon Jennings, graciously gave up his seat to Richardson, who was running a fever. Holly reportedly needled Jennings about his decision, telling him, “I hope your old bus freezes up.” Jennings responded: “Well, I hope your plane crashes.” Crash it did, into a snowy Iowa field, shortly after takeoff, killing everyone aboard, and forever memorializing February 3, 1959 as “The Day the Music Died.”