Lou Barlow was the bass player for alternative rock band Dinosaur Jr in the late 1980s. While both Barlow and leader J Mascis wrote songs, Mascis' material dominated the group's output because Barlow was intimidated by the guitarist's songwriting efforts.[1] Barlow spent progressively more time recording his own songs at home. Barlow and Gaffney released the Weed Forestin' cassette in 1987 on Homestead Records under the name Sebadoh, which was a nonsense word Barlow often muttered in his recordings.[2]. Both Barlow and Gaffney contributed songs to 1988's The Freed Man cassette. Homestead Records head Gerard Cosloy heard the cassette release of The Freed Man and released it as a full-length album on Homestead in 1989. Soon after the cassette's release Barlow was kicked out of Dinosaur Jr. Over time Sebadoh's releases became a way for Barlow to address the issues of control that manifested as the tension in and his ejection from Dinosaur Jr; Barlow said "I got a lot of hatred out just by writing those songs."

Jason Loewenstein joined in summer 1989, the first release that he played on being the "Gimme Indie Rock" single in 1991. Only ten 'band' shows were performed throughout Western Mass, Boston, and New York over the period 1989-1990 before third album, the appropriately-named Sebadoh III was released.