Born near Abilene, Texas most of his youth was spent in Littlefield a small town on the high plains of West Texas where with his older brother Waylon listened to old cowboy and country songs that their dad sang. The boys learned to sing together and started entering talent contests around their hometown.
Tommy served two years in the military and when he finished his service he moved to Phoenix to join Waylon as his bass player. This was the early development of what became known as the outlaw sound. Nashville, Tennessee was next as Waylon signed with RCA and Tommy became Waylon's manager while still playing bass and singing in his band. Over the years, Waylon and Tommy worked in partnership in the music business.