Guster became one of the most successful bands to hit the U.S. East Coast scene in the late 1990s. Through relentless touring and humorous stage banter with the crowd, the band developed a strong grass-roots fan base which spread rapidly with a strong presence on the Internet. The Boston trio developed a unique sound with two acoustic guitars and a bongo set, successfully defying the typical industry pigeonholing. They wrote short, infectiously catchy tunes about love, suicide and absurdist rock star lifestyles. Through word of mouth alone, the band sold over 40,000 copies of independent debut Parachute and their second effort, Goldfly.

Ryan Miller (guitar, vocals), Adam Gardner (guitar, vocals) and Brian Rosenworcel (percussion) met in 1992 at Tufts University, and played around the Boston area during college. Originally named Gus, the band adopted the appended Guster moniker after discovering several other national touring acts playing under the same name. In 1994 they recruited producer Mike Denneen for their debut album, Parachute, which the Boston Globe named Best Local Debut Album in 1995. Guster also appeared on the AWARE 3 Compilation the same year. Within a couple of years from its inception, Guster became one of the most popular bands in the area. Named the Best Live Act at the Boston Music Awards in 1997, Guster was hailed as one of the greatest independent successes of the 1990s, achieving a reputation as one of the most reputable unpromoted bands of the decade.

After releasing a second album, Goldfly, in March 1997, Guster continued a relentless touring schedule, taking their live formula for success and selling out small clubs across the country. The group credited a significant amount of success to their "Rep Program," a roots-level marketing campaign run by dedicated fans. Guster Reps distributed flyers and spread the word about the quirky band entirely through voluntary efforts.