Conlee was born on a tobacco farm in Versailles, Kentucky.
Conlee did not immediately take up a musical career, instead becoming a licensed mortician, employed by Duell-Clark Funeral Chapel, and later a disc jockey at radio station WLA.
By age 10, Conlee had begun singing and playing guitar, and later sang tenor in a barbershop quartet.
Conlee has been a member of the Grand Ole Opry since 1981.
Between 1978 and 2004, Conlee charted a total of 32 singles on the Billboard Hot Country Songs charts, and recorded 11 studio albums.