[5] His commercial breakthrough came in 1996 with the release of Sweet Relief II: Gravity of the Situation, a charity record of alternative artists covering his songs.

His musical style has been described by Bryan Carroll of AllMusic as a "skewed, refracted version of Americana that is haunting, funny, poignant, and occasionally mystical, usually all at once".

[8] At 18, while drinking and driving,[9] a car accident left him partially paralyzed; in a December 1, 2009, interview with Terry Gross on her NPR show Fresh Air, he said he was "a quadriplegic from [his] neck down", and although he had feeling and some movement in his body, he could not walk "functionally" and that, although he realized shortly afterward that he could still play guitar, he could only play simple chords.

[8] After his recovery he left Zebulon and moved to Nashville, Tennessee; the poetry he read there (by Stevie Smith, Walt Whitman, Wallace Stevens, W. H. Auden, Stephen Crane and Emily Dickinson) served to inspire and influence him.

[10] Around 1985, Chesnutt moved to Athens and joined the band La-Di-Das with future member of the Dashboard Saviors Todd McBride.

[10][11] 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.

Chesnutt also had a small role as "Terence" in the 1996 Billy Bob Thornton movie Sling Blade, which he later described self-mockingly as a poor performance.

The music includes improvisations, interpretations of Johann Strauss I's "Radetzky March", and renditions of a number of Vic Chesnutt songs.

The result was a string of film vignettes bound by the poetry of Roth's writing and by the sounds and songs of the live musicians.

The 2005 album Ghetto Bells featured famed guitarist Bill Frisell, whom Chesnutt met in 2004 at the Century of Song concert series at the German festival Ruhrtriennale.

[24] In 2009, he sang on the track "Grim Augury" from the album Dark Night of the Soul by Danger Mouse of Gnarls Barkley, Sparklehorse, and director David Lynch.

In 2004, New West also re-released the early Texas Hotel recordings, including expanded liner notes and extra tracks.

He contributed the track, "Weed to the Rescue", to the 1998 Hempilation II charity album, with proceeds going to NORML, an American organization dedicated to marijuana legalization.

Chesnutt recorded a version of the song that was released on the 2004 compilation CD, The Late Great Daniel Johnston: Discovered Covered.

[6] In his final interview, which aired on National Public Radio 24 days before his death, Chesnutt said that he had "attempted suicide three or four times [before].

"[8] According to him in the same interview, being "uninsurable" due to his quadriplegia, he was $50,000 in debt for his medical bills, and had been putting off a surgery for a year ("And, I mean, I could die only because I cannot afford to go in there again.