Around 1985, Vic Chesnutt moved to Athens and joined the band, La-Di-Das, with future member of the Dashboard Saviors Todd McBride. 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 went on to produce Chesnutt’s first two albums, Little (1990) and West of Rome (1991). In 1993, Chesnutt was the subject of filmmaker Peter Sillen’s independently produced documentary, Speed Racer: Welcome to the World of Vic Chesnutt, which was shown on PBS. 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. In 1996, Chesnutt was exposed to a wider audience with the release of the charity record Sweet Relief II: Gravity of the Situation, the proceeds from which went to the Sweet Relief Fund. The album consisted of Chesnutt covers by famous musicians including Cracker, Garbage, The Smashing Pumpkins (with Red Red Meat), Madonna, R.E.M., Soul Asylum, and Live. For the 2007 edition of the Vienna International Film Festival (Viennale), New York filmmaker Jem Cohen was commissioned to close the festival, which he did with his program entitled, “Evening’s Civil Twilight In Empires Of Tin.” An impressionistic narrative was constructed through live readings from the texts of Joseph Roth and a live musical score performed by Vic Chesnutt, members from Thee Silver Mt Zion Memorial Orchestra, Guy Piciotto (Fugazi), and The Quavers. The music includes improvisations, wonderfully blown-out interpretations of Johann Strauss I’s “Radetzky March”, and bracing renditions of a number of Vic Chesnutt songs. The result is a sort of agit-prop hallucination, a string of film vignettes bound by the poetry of Roth’s writing and by the sounds and songs of the live musicians. A DVD of the program was released in 2009.

Vic Chesnutt collaborated with Bob Mould to record a version of Gram Parsons’ song, “Hickory Wind,” which appeared on the 1993 compilation, Conmemorativo: A Tribute to Gram Parsons. He recorded with many other groups and artists. He made two albums with fellow Athens group Widespread Panic, under the name of brute. Chesnutt wrote “Aunt Avis” and co-wrote “Blight” and “Protein-Drink/Sewing-Machine”, which are often performed live by Widespread Panic. “Aunt Avis” appeared on WSP’s album Bombs & Butterflies, and Chesnutt made a guest appearance as well. The 1997 video for “Aunt Avis” was directed by Billy Bob Thornton and featured Chesnutt. After getting to know engineer Scott Stuckey during the recording of West of Rome, Stuckey and Chesnutt became close friends and would go on to collaborate on various projects including producing two more albums together, co-writing “Weed to the Rescue” for the Hempilation album, as well as working on numerous videos including “Ladle” for Capitol Records. At the time of his death, Chesnutt and Stuckey were working on a documentary about Chesnutt’s music. The film, tentatively titled “Degenerate”, was scheduled to be released in 2012. Vic Chesnutt’s 1998 album The Salesman and Bernadette was recorded with alt-country group Lambchop as the backing band. The album Merriment was a collaborative effort between Chesnutt and Kelly and Nikki Keneipp, with Chesnutt writing and singing the songs, and the Keneipps playing the music.

Vic Chesnutt was featured singing on the title track of Elf Power’s 2004 release, Walking With the Beggar Boys. 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. Ghetto Bells also featured lyricist and composer Van Dyke Parks on accordion and keyboards. Chesnutt’s wife, Tina, would frequently play bass on his albums, including Ghetto Bells. His niece, and fellow songwriter, Liz Durrett also appeared on the album. In the winter of 2006, he recorded North Star Deserter at the Hotel2Tango in Montreal. It was released on September 11, 2007 by Constellation Records. The record included contributions from Constellation artists Thee Silver Mt. Zion Memorial Orchestra & Tra-La-La Band, members of Godspeed You! Black Emperor, as well as Fugazi’s Guy Picciotto. The album was produced by documentary filmmaker Jem Cohen. In 2008, Athens, Georgia based Elephant 6 collective recording artists Elf Power collaborated with Chesnutt on the album Dark Developments, released as Vic Chesnutt, Elf Power, and the Amorphous Strums. The “amorphous strums” refers to Curtiss Pernice and Sam Mixon, who also played on the album. In 2009, Chesnutt worked with many of the same contributors to the album North Star Deserter to release the album At the Cut in September. As with North Star Deserter, the album was recorded in Montreal and released on Constellation Records. Later in 2009, Vic recorded the album titled Skitter on Take-off with Jonathan Richman which was inspired by the two albums recorded in Montreal and was released on Vapor.

In 2009, Vic Chesnutt 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. Mark Linkous had previously attempted to collaborate with Chesnutt on previous Sparklehorse albums such as Good Morning Spider however Chesnutt was unable to feature in person on the album. Instead, a recorded voice message he left Linkous apologising for his inability to show was used on the song “Sunshine”. Chesnutt’s first four albums were released on the independent Texas Hotel label. He then recorded About to Choke (1996) for Capitol Records. The Salesman and Bernadette (1998) was on PolyGram; Merriment (2000) was on the Backburner Records label; spinART was the label for the self-performed and recorded Left to His Own Devices (2001). Chesnutt then found a home at the New West Records label, which released two of his albums. In 2004, New West also re-released the early Texas Hotel recordings, including expanded liner notes and extra tracks. in 2010: About to Choke was re-released on 180 gram vinyl on the Four Men with Beards label and is being distributed by City Hall Records. On December 25, 2009, at the age of 45, Vic Chesnutt died from an overdose of muscle relaxants that had left him in a coma in an Athens hospital. 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]. It didn’t take.”