He was born near Kosse, Texas; his father was a fiddle player who along with his grandfather, taught the young Wills to play the fiddle and the mandolin. After several years of drifting, "Jim Rob," then in his 20s, attended barber school, got married, and moved first to Roy, New Mexico then to Turkey, Texas (now considered his home town) to be a barber. He alternated barbering and fiddling even when he moved to Fort Worth to pursue a career in music. It was there that while performing in a medicine show, where he learned comic timing and some of the famous "patter" he later delivered on his records, the show's owner gave him the nickname "Bob."