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." In Fort Worth, Wills met Herman Arnspinger and formed The Wills Fiddle Band. ...show more

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." In Fort Worth, Wills met Herman Arnspinger and formed The Wills Fiddle Band.

In 1930 Milton Brown joined the group as lead vocalist and brought a sense of innovation and experimentation to the band, now called the Light Crust Doughboys due to radio sponsorship by the makers of Light Crust Flour. Brown left the band in 1932 to form the Musical Brownies, the first true Western swing band. Brown added twin fiddles, tenor banjo and slap bass, pointing the music in the direction of swing, which they played on local radio and at dancehalls. Wills remained with the Doughboys and replaced Brown with new singer Tommy Duncan in 1932.

He found himself unnable to get along with future Texas Governor W. Lee "Pappy" O'Daniel, the authoritarian host of the Light Crust Doughboy radio show. O'Daniel had parlayed the show's popularity into growing power within Light Crust Flour's parent company, Burrus Mill and Elevator Company and wound up as General Manager, though he despised what he considered "hillbilly music." Wills and Duncan left the Doughboys in 1933 after Wills had missed one show too many due to his sporadic drinking. After forming a new band, "The Playboys" and relocating to Waco, Wills found enough popularity there to decide on a bigger market. ...show less