Finding himself beneath the spell cast by local bands like the Rain Parade and the Dream Syndicate, Phillips soon partnered with Stockton acquaintance Jeff Clark to form Shiva Burlesque. The band dissolved after two critically acclaimed records, and Phillips began writing and demoing under the Grant Lee Buffalo alias. Following several solo performances, he invited former bandmates Joey Peters and Paul Kimble to join him, and the trio signed to the Warner Bros subsidiary Slash Records in 1992.

Phillips' golden, honey-soaked voice had largely gone to waste in Shiva Burlesque, but the new band enabled him to step out as a singer/songwriter and multi-instrumentalist. Grant Lee Buffalo went on to release four very different LPs, although a cult following, several successful tours, and across-the-board critical acclaim (Phillips was voted Rolling Stone's Male Vocalist of the Year following the second LP) didn't translate into strong sales. Frustrated with his label's dead-on-arrival promotion, Phillips asked for his band to be released from their contract, and he was obliged. (It was erroneously reported that he had been dropped.) Phillips dissolved his band, anxious to forge a new path.

In October of 1999, he headed to Jon Brion's studio and recorded a handful of new songs, played exclusively by himself. Dubbed Ladies' Love Oracle, the album was self-released the following year online; Phillips also sold it during his numerous appearances at Largo in Hollywood. After landing a new contract with Zoe/Rounder -- and making the first of many appearances on the popular comedy-drama Gilmore Girls, as a roaming town troubadour -- he issued the excellent Mobilize in 2001. The next year, Rounder reissued Ladies' Love Oracle in time for Phillips' joint tour with Kristin Hersh and Joe Doe. Virginia Creeper followed in 2004, marking the first time that Phillips had consciously eschewed all electric guitars in favor of a stripped-down, folksy sound. A covers album, Nineteeneighties, appeared in 2006, and Strangelet arrived one year later. For his next effort, Phillips assembled a band that featured Jay Bellerose, Paul Bryan, and Jamie Edwards, all of whom spent five days recording 2009's Little Moon.

In October 2012, Phillips, who is descended from the Creek and Cherokee Native American tribes, released the album Walking in the Green Corn, featuring several songs informed by his indigenous heritage. In 2013, Phillips and his family left California to settle in Tennessee. Teaming with a handful of Nashville musicians, he recorded The Narrows, released on March 18, 2016 by Yep Roc Records. ~ Andy Kellman