He was born near Kosse, Texas and his father was a fiddle player who taught the young Wills to play the fiddle and the mandolin. In his 20s 'Bob' attended barber school, got married and moved to Turkey, Texas to be a barber. He regularly entered fiddle contests in West Texas, New Mexico and Oklahoma and soon the fiddle had replaced the scissors in the young Wills' imagination and he headed to Fort Worth.
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 Flower. Brown added twin fiddles, tenor banjo and slap bass and pointed the music in the direction of swing. The band split up though with Wills going on to form The Texas Playboys, with new singer Tommy Duncan, while Milton Brown formed his own band, Milton Brown and his Musical Brownies.
After relocating the band to Waco, then Oklahoma City, Wills eventually settled in Tulsa, Oklahoma and began broadcasting noontime shows over the 50,000 watt KVOO radio station. By 1935 Wills had added horn and reed players to the Playboys and the band numbered 13. The addition of steel guitar wiz Leon McAuliffe provided the final ingredient to the development of western swing. With its jazz sophistication and blues influence, plus improvised scats and wisecrack commentary by Wills, the band became the first superstars of the genre. In 1940 "San Antonio Rose" sold a million records and became the signature song of The Texas Playboys.