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. Wooley was diagnosed with leukemia in 1996, which forced him to retire from public performing in 1999. After seven years of battling the illness, he died at the age of 82 at the Skyline Medical Center in Nashville, Tennessee, on September 16, 2003. He was entombed in Hendersonville Memory Gardens in Hendersonville, Tennessee.