Joe Diffie was regarded by many of his peers as one of the better vocalists in contemporary country, and lent his traditional sensibilities to humorous, rock-tinged novelties and plaintive ballads. Diffie was born in Tulsa, Oklahoma, in 1958 and grew up in a musical family, first performing in public at age four with his aunt's country band. He played in a rock band during high school, and later moved on to a gospel quartet and, during college, a bluegrass band called the Special Edition. He worked on his songwriting and singing over the next few years while working in a foundry, and caught a break when his "Love on the Rocks" was recorded by Hank Thompson. When Randy Travis nearly recorded another of his songs, Diffie was convinced he had a shot in the business, and moved to Nashville in 1986. He took a job at the Gibson guitar plant while continuing to write songs, and became an in-demand demo singer as well. Holly Dunn's 1989 recording of a Diffie collaboration, "There Goes My Heart Again," proved a major hit, and Diffie found himself a hot commodity. He signed with Epic and released his debut album, A Thousand Winding Roads, in 1990. His first single, "Home," went all the way to number one on the country charts, and "If the Devil Danced (In Empty Pockets)" duplicated that feat; meanwhile, two more singles from the album, "If You Want Me To" and "New Way (To Light Up an Old Flame)," reached number two.