Around 1985, Chesnutt moved to Athens and joined the band, The La-Di-Da’s. After leaving that group he began performing solo on a regular basis at the 40 Watt Club; it was there that he was spotted by Michael Stipe of R.E.M.; Stipe produced Chesnutt’s first two albums, Little (1990) and West of Rome (1991).
In 1992 Chesnutt was the subject of a PBS documentary, Speed Racer. He also had a small role in the 1996 Billy Bob Thornton movie Sling Blade which he later described self-mockingly as a poor performance.
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