After leaving his band Eliot in 1993, guitarist Seth Cohen was interviewed by the Chicago weekly "New City." When asked what he might do next, Cohen mentioned attending a show featuring Unrest, Gastr del Sol and Stereolab. This caught the attention of guitarist Pat O'Connell and drummer Michael Lenzi, who both called Cohen after reading the article. As a result, the three formed Number One Cup. They released their first single, "Connecticut, " and started playing some shows. Cohen's former Eliot bandmate John Przyborowski filled in on bass until the band recruited Jenni Synder. They released their second single, "Indie Softcore Denial, " before Synder left the band. The trio then signed with Flydaddy Records and released their debut full-length, Possum Trot Plan in 1995. Pat "Tiger" Reis briefly joined the band on bass, but it didn't work out so Przyborowski once again filled in. He eventually joined the band full-time. In 1998, after recording their third album, People, People, Why Are We Fighting?, disaster struck. Cohen broke his neck while playing hockey, and tour plans had to be postponed until he recovered. The band threw a record release party where 12 Chicago bands played cover versions of the new album's songs. Shortly thereafter, Przyborowski left the band and was replaced by Kurt Volk.