Wooley married for the first time in 1940, wedding 17-year-old Melva Miller, a cousin of Roger Miller who would later become a successful song writer and actor himself. Wooley became friends with Miller when he lived in Oklahoma. He taught the boy how to play guitar chords and bought him his first fiddle.
Wooley was married five times. His first wife was Melva Miller, whom he married in 1940. Six years later he married Edna Talbott Bunt in Fort Worth, Texas. His third wife was Beverly Irene Addington. He and Beverly remained together for 19 years and adopted one daughter, Chrystie Lynn. Then, in 1985, he married Deanna Grughlin and then his manager Linda Dotson, who already had a daughter, Shauna.