Barrett has spent the majority of his musical career playing with the Mighty Mighty Bosstones. He appeared on eight full-length albums, three EPs and a live album with the Bosstones, as well as touring continuously throughout the world, until the band's announcement of a hiatus in December 2003. The band's 1997 release, "Let's Face It", would prove to be the band's biggest break, mostly due to the first single "The Impression That I Get," which charted at number one on the Billboard charts.