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A singer, fiddler, and guitarist who became a star in both country and bluegrass, Clinton Gregory was born in Martinville, Virginia on March 1, 1966. Gregory grew up surrounded by music; his father, Willie Gregory, was a gifted fiddler who came from a long line of musicians and encouraged his son to follow in his footsteps. Clinton began playing the violin when he was five years old, and a year later he was good enough to perform at bluegrass festivals. When Clinton was 12, his family relocated to Nashville, Tennessee, where Willie had landed a gig at the Grand Ole Opry. As Clinton continued to focus on his music, he developed a reputation of his own in the Music City, and began working steadily as a sideman and session player with some of the leading country acts of the day. In 1990, Gregory stepped into the spotlight by releasing his first solo album, Music 'n Me, for the independent country label Step One Records. The album was well-received, but it was Clinton's second long-player, 1991's If It Weren't for Country Music I'd Go Crazy, that proved to be his commercial breakthrough. The title tune became a hit, peaking at 26 on the country singles charts, and three other tunes from the LP earned airplay as singles.
Released in 1992, Freeborn Man spawned Gregory's biggest hit, the single "Play, Ruby, Play," which rose to 25 on the country singles survey, and another tune from the album, "Who Needs It," fared nearly as well, topping out at 29. By this time, Gregory was sharing stages with the likes of Willie Nelson, Garth Brooks, Marty Stuart, Pam Tillis, and Hank Williams, Jr., and he appeared frequently at the Grand Ole Opry. (In February 1992, Clinton performed on the Opry stage alongside his father, who died only two months later.) However, after the 1993 album Master of Illusion failed to live up to commercial expectations, Clinton left Step One for a major-label, Polydor. His first album for Polydor, 1995's Clinton Gregory, sold modestly, and a variety of professional and personal setbacks soon followed. For the better part of the next ten years, Gregory was off the music industry's radar during his period of struggle, but in 2005 he returned to music thanks to Neil Young. Young invited Gregory to play on his album Prairie Wind, and to join his band for the concerts that were filmed for the documentary Neil Young: Heart of Gold. In the wake of his work with Young, Gregory made his way back into performing and songwriting, and in 2012 he completed his first album in 17 years, Too Much Ain't Enough. Released by the independent Melody Roundup label, Too Much Ain't Enough was well received by critics and fans, and a second album, the bluegrass-oriented The Roots of My Raising, appeared in 2013.