The New York City-based power pop band Fountains of Wayne is anchored by the singer/songwriter duo of Adam Schlesinger and Chris Collingwood, who first teamed together in 1986 while studying at Massachusetts' Williams College. Sharing a mutual affection for melodic British pop, they formed a series of short-lived bands before recording an LP under the name Pinnwheel. Legal hassles blocked the album's release, however, and the duo went their separate ways, with Schlesinger resurfacing in the N.Y.C. indie pop band Ivy and Collingwood joining the Boston country group Mercy Buckets. They reunited in 1996 as Fountains of Wayne (so named in honor of a lawn ornament store in Wayne, NJ) and issued their acclaimed self-titled LP on Atlantic; that same year, Schlesinger also enjoyed success as the author of the title theme to Tom Hanks' ock & roll movie That Thing You Do! Schlesinger's addition to the hit soundtrack garnered a Grammy nomination and an RIAA gold certification in 1997. While Fountains of Wayne's debut did not enjoy similar success, selling only 125,000 copies in the U.S., the band nevertheless toured the world alongside the Lemonheads and the Smashing Pumpkins (whose guitarist James Iha would prove to be an important champion of the group). Guitarist Jody Porter and ex-Posies drummer Brian Young joined FOW's touring lineup, later becoming official members with the band's sophomore release.

Fountains of Wayne's follow-up effort, Utopia Parkway, arrived in 1999, and the single "Denise" was a modest hit at college radio. However, like its predecessor, the album sold poorly despite being warmly received by critics. Frustrations subsequently grew between Fountains of Wayne and Atlantic, who neglected to promote the standout track "Trouble Times" as a single, and the band was dropped from the Atlantic roster in late 1999. A long hiatus followed, during which Schlesinger co-wrote several songs for the Josie and the Pussycats soundtrack, released a third album with Ivy, and produced albums for the Verve Pipe, David Mead, and They Might Be Giants.