Formed in Basking Ridge, New Jersey in 1980, the band Uncle Green consisted of Matt Brown (guitar and vocals), Jeff Jensen (guitar, vocals), Bill Decker (bass and keyboards), Pete McDade (drums), and Danny Giordano (tambourine and vocals). Brown and Jensen were the principal songwriters and vocalists for the group.
After relocating to Atlanta, the band recorded a single, "Holes" b/w "Heaven", in 1986, and two independent records, Get It Together and 15 Dryden, for New Vision Records in 1987 and 1988. Creative differences led Giordano to leave Atlanta for New York after the first LP, where he formed the band Humbolts. Uncle Green soon met an ascendant Brendan O'Brien, near the beginning of his producing career, with whom they recorded the albums You and What An Experiment His Head Was for DB Records. After establishing themselves as a well-known regional college-rock band, they signed a contract with Atlantic Records in 1992 and recorded Book of Bad Thoughts. Like all of their efforts, the album was lauded by critics, but establishing commercial viability proved more difficult. Subsequent tours supporting The Reivers, Semisonic, The Black Crowes, Matthew Sweet, They Might Be Giants, Robyn Hitchcock and Ben Folds Five helped increased their visibility.
In 1994, the band took part in the Indigo Girls project Jesus Christ Superstar: A Resurrection and appear on the studio cast album. In 1995 part of a solo Matt Brown set recorded at Eddie's Attic in Decatur, Georgia, was included on the album Solo, Volume I, released by the independent label Sister Ruby. The album included original songs that do not appear on any of the group's albums, as well as a cover of Big Star's "Nighttime". The same year, Uncle Green contributed a version of "Ballad of a Thin Man" to A Tribute to Bob Dylan, Vol. 2, also on the Sister Ruby label.