Combining jazz with country, Vassar Clements became one of the most distinctive, inventive, and popular fiddlers in bluegrass music. Clements first came to prominence as a member of Bill Monroe's band in the early '50s, but he never limited himself to traditional bluegrass. Over the next four decades, he distinguished himself by incorporating a number of different genres into his style. In the process, he became not only one of the most respected fiddlers in bluegrass, he also became a sought-after session musician, playing with artists as diverse as the Monkees, Hank Williams, Paul McCartney, Michelle Shocked, Vince Gill, and Bonnie Raitt.

Vassar Clements taught himself to play fiddle at the age of seven. Soon afterward, he formed a band with two of his cousins. By the time he was 21, Clements' skills were impressive enough to attract the attention of Bill Monroe. Monroe hired the young fiddler and Clements appeared on the Grand Ole Opry with the mandolinist in 1949. The following year, the fiddler recorded his first session with Monroe.

For the next six years, Clements stayed with Monroe's band, occasionally leaving for brief periods of time. In 1957 he joined Jim & Jesse's Virginia Boys, and stayed with the band for the next four years. In the early '60s Clements was sidelined for a while as he suffered from alcoholism. By the end of the '60s he had rehabilitated, and he returned to playing in 1967. That year he moved to Nashville and began playing the tenor banjo at a residency at the Dixieland Landing Club. In 1969 he toured with Faron Young and joined John Hartford's Dobrolic Plectorial Society. The band only lasted ten months, and after its breakup Clements joined the Earl Scruggs Revue; he stayed with that band for a year.

Clements began playing sessions in 1971, appearing on albums by Steve Goodman, Gordon Lightfoot, David Bromberg, J