[4][better source needed] Stuart began his music career by performing in small venues, including clubs, coffee houses and college campuses.
[3][5] Stuart formed the Chicago-based band Gravity Beavers in June 1990, with three other members – Arch Alcantara, Howie Kantoff and Doug Kenrick.
[6] Stuart listed the now defunct band's influences as Kansas, Cat Stevens, Neil Young and Jimi Hendrix in a January 1992 Chicago Tribune article.
[6] In 1994, Stuart joined the combined Tori Amos and Cracker tour as their opening act, appearing as an acoustic solo or occasionally with a backup bassist.
[10] Stuart sang with Dog's Eye View on Sweet Relief II: Gravity of the Situation, a 1996 tribute album dedicated to Vic Chesnutt.
[11] Stuart left Dog's Eye View after the release of the band's second album, Daisy, a commercial disappointment,[10] to pursue solo work.
[13] Speaking to ABC News at the time, Matchbox Twenty vocalist Rob Thomas praised Stuart's yet unreleased album saying, "Peter's one of my dearest friends.
[10][15] Other guest artists who contributed to Stuart's solo debut included Mark Isham, D. J. Bonebrake, Greg Leisz, a multi-instrumentalist who added some guitar work, as well as David Immergluck and Charlie Gillingham, both of Counting Crows.
[17] It featured backing vocals by singers Jason Mraz and Kelly Moneymaker, as well as an appearance from Paul Doucette of Matchbox Twenty.