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 GLP 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.