Allsup worked with entertainers such as Buddy Holly, including playing lead guitar on "It's So Easy!" and "Lonesome Tears", as well as playing with Bob Wills &amp; His Texas Playboys. Allsup was touring with Holly, Ritchie Valens, and J.P. "The Big Bopper" Richardson when he serendipitously lost a fateful coin toss with Valens for a seat on the plane that crashed, killing Valens, Holly, Richardson, and pilot Roger Peterson on February 3, 1959. Investigators initially thought that Allsup had died in the crash due to the fact that he had given Holly his wallet so that Holly could use Allsup's ID to claim a mailed letter on his behalf. Allsup moved to Los Angeles, played with local bands, and did session work, including a songwriting credit for The Ventures, "Guitar Twist".