Born in Martinville, VA, Clinton Gregory came from a long line of fiddle players. He picked up the fiddle at five years old and made his performing debut at bluegrass festivals within a year. He came to Nashville at age 12, where his father, Willie Gregory, was playing at the Grand Ole Opry. When word of Clinton's fiddle prowess got around in Nashville, he was rarely without a steady gig and played on numerous studio sessions that included Dennis Robbbins, the McCarters, and Suzy Bogguss. In 1990, Step One Records signed him to their label. His debut single, a rendition of the Jimmie Davis classic "Nobody's Darlin' But Mine," was followed by a string of country singles, including "Couldn't Love Have Picked a Better Place To Die," "One Shot at a Time," and the Top 20 hit "Play Ruby Play," which was also a video hit on both CMT and TNN.