After stints in the bands Cutgrass and Verbena, he became the leader of Taylor and the Puffs and released You Know That Summers Comin' in March 2004. He made his solo debut with the EP Shoot Me, Shoot Me, Heaven later that year, followed in January 2005 by his first full-length solo album, Tragic City. His second solo effort, Bad Little Kitty, was released by Mass Music in July 2008 as he embarked on a tour. Hollingsworth then joined Conor Oberst as part of the Mystic Valley Band, Oberst's first post-Bright Eyes project. Although he also served as a sideman with Maria Taylor, Hollingsworth's focus remained with the Mystic Valley Band, as he co-wrote several songs for the band's sophomore album, 2009's Outer South, and toured with the band in support of the record. That same year, Hollingsworth found time to issue Life with a Slow Ear, a stripped-down solo album that focused on little more than his voice and acoustic guitar. ~ William Ruhlmann