ran track; in his senior year, he was recognized as Best All-Around Male Athlete. After graduating, he attended Cameron University in Lawton, Oklahoma. Although he initially earned credits toward medical school, he decided against a medical profession after marrying for the first time in 1977 and ultimately dropped out before graduation. He first worked in oil fields, then drove a truck that pumped concrete in the oilfield in Alice, Texas, before moving back to Duncan to work in a foundry. During this period, he worked as a musician on the side, first in a gospel group, Higher Purpose, then in a bluegrass band, Special Edition. He built a recording studio, began touring adjacent states with Special Edition, and sent demonstration recordings to publishers in Nashville. Hank Thompson recorded Diffie's "Love on the Rocks", and Randy Travis bought rights to one of Diffie's songs but did not record it. When the foundry closed in 1986, Diffie declared bankruptcy and sold the studio out of financial necessity. He also divorced his wife, who left with their two children. He spent several months in a state of depression before deciding to move to Nashville, Tennessee, where he took a job at Gibson Guitar Corporation. At Gibson, he contacted a songwriter and recorded more demos, including songs that would later be recorded by Ricky Van Shelton, Billy Dean, Alabama, and the Forester Sisters. By mid-1989, he left Gibson to record demos full-time. He also met Debbie, who later became his second wife. That year, he was contacted by Bob Montgomery, a songwriter and record producer known for working with Buddy Holly. Montgomery, who was then the vice president of A&R at Epic Records, told Diffie he wanted to sign him with the label, but had to put him on hold for a year. Meanwhile, Holly Dunn released Diffie's song "There Goes My Heart Again", where Diffie also sang backing vocals. Following the song's chart success, Diffie signed with Epic in early 1990. Professional music career 1990–1991: A Thousand Winding Roads The label released Diffie's debut album, A Thousand Winding Roads, at the end of 1990, with Montgomery and Johnny Slate as producers. Its first single, "Home", reached the top of the Billboard Hot Country Songs chart. The song also reached number one on the country music charts published by Radio & Records and Gavin Report, making him the first country music artist to have