Benson was raised Jewish. In 1970, Benson, a native of Philadelphia, formed Asleep at the Wheel with friends Lucky Oceans and Leroy Preston in Paw Paw, West Virginia. They were soon joined by Gene Dobkin, a classmate of Benson's at Antioch College, and Chris O'Connell. The group relocated to Austin in 1973 after a suggestion from Willie Nelson.
