He is the lead singer and songwriter of the alternative rock group Toad the Wet Sprocket and also records and performs as a solo artist.

[6] The band recorded five albums but broke up in 1998, after escalating tensions, shortly after Phillips' father died of colon cancer.

In 2005, Phillips returned to a major label via Universal Music Group's imprint Lost Highway Records and released the critically acclaimed Winter Pays For Summer.

The album included the radio single "Duck and Cover," but Phillips and the label parted ways due to creative differences.

A compilation of six outtakes from the album were published as an EP titled Unlucky 7, the first track ("The Hole") of which was featured in the second episode of the AMC television series Breaking Bad.

[15][16] In 2009, Phillips recorded a cover version of The Beatles' song "I'll Follow the Sun" for the soundtrack of the film Imagine That.

[19] On October 8, 2008, Phillips injured his arm while at a friend's house, where he was sitting on a glass coffee table that collapsed when he moved back.