Dempsey was born on October 21, 1958 to Hobert and Doris Biles in Lubbock, Texas. Survivors include his grandsons Tyler and Logan Wilson and Zane Killian; his mother, Doris Young, sister, Dede Kirkpatrick, sister-in-law Stephanie Biles, nieces Morgan Kirkpatrick, Kelsey Hennesay, and Marsha Biles. He was preceded in death by his father, Hobert Biles, his daughter, Chasity Killian and his brother, Doug Biles. His family extends a special thanks to Gretchen with Hospice of the Southwest and Robert and Kathy Dean.
Dempsey worked in construction all of his life, starting with his dad. He worked for Jay Boy Adams remodeling tour buses, where he was able to meet musicians such as Clint Black, ZZ Top, and many more. Eventually, he founded a business with his brother, Doug, and later went on to start his own business. His latest specialty was pocket doors. Dempsey loved to fish and shoot competitively.