Fulks got his first significant exposure via Bloodshot Records' 1994 compilation Insurgent Country, Vol. 1: For a Life of Sin, which included his track "Cigarette State"; the 1995 follow-up, Insurgent Country, Vol. 2: Hell-Bent, featured Fulks' "She Took a Lot of Pills (And Died)." Both cuts were produced by Steve Albini, who also helmed Fulks' Bloodshot debut, Country Love Songs, in 1996. The album received highly positive reviews and featured backing from roots rockers the Skeletons, as well as former Buck Owens steel guitarist Tom Brumley. The follow-up, South Mouth, took a similarly retro-minded approach, drawing from classic honky tonk and Bakersfield country. With a growing cult reputation, Fulks earned a major-label shot with Geffen, but many critics felt that his 1998 label debut, Let's Kill Saturday Night, undermined the organic strengths of his previous work with overly slick roots rock production. A merger between Universal and PolyGram shortly after the release of Let's Kill Saturday Night led to a gutting of the Geffen artist roster, and the album died on the vine as Fulks found himself without a label.

Fulks opted to start his own label, Boondoggle Records, distributed by his friends at Bloodshot, and launched it with The Very Best of Robbie Fulks, a facetiously titled collection of demos and unreleased recordings. In 2001, Fulks followed with 13 Hillbilly Giants, in which he covered a bakers' dozen songs of the 1950s and '60s, and later that year he issued his most ambitious set to date, Couples in Trouble, a bleak but compelling collection of original songs about a variety of failing relationships that found Fulks adding new dimensions to his interest in rock and left-field pop. In 2005, Fulks signed to the roots-oriented Yep Roc label and dug back into his country roots with his first album for the label, Georgia Hard. It was followed by the live collection Revenge in 2007.