Vee's career began in the midst of tragedy. On February 3, 1959, "The Day the Music Died," three of the four headline acts in the lineup of the traveling Winter Dance Party—Buddy Holly, Ritchie Valens, and the Big Bopper—were killed in the crash of a V-tailed 1947 Beechcraft Bonanza airplane, along with the 21-year-old pilot, Roger Peterson. (Dion DiMucci, the fourth headliner, had opted not to travel on the plane.) It crashed near Clear Lake, Iowa, en route to the next show on the tour itinerary, in Moorhead, Minnesota. Vee, then 15 years old, and a hastily assembled band of Fargo schoolboys (including his older brother Bill) calling themselves the Shadows volunteered for and were given the unenviable job of filling in for Holly and his band at the Moorhead engagement. Their performance there was a success, and started Vee's career as a popular singer.