Brannan appeared in the 2006 movie Shortbus, which included one of his songs in its soundtrack, and began to build a fan base by performing on YouTube.

[6][7] Brannan went to college for one semester in Cincinnati, Ohio, and went to California, first to Palm Springs and later to Los Angeles, trying to become an actor.

[9] Brannan began to record sparse music videos for YouTube, accompanying himself on the guitar, and built an international fan base without corporate sponsorship, using MySpace and Blogspot.

[11] His second album, In Living Cover, was released in 2009 and reached number ten on the Billboard Top Heatseekers chart for the week of July 25, 2009.

[3] Allmusic described his style as contemporary singer-songwriter and compared him to female artists, including Ani DiFranco, Lisa Loeb, Sinéad O'Connor, and Liz Phair.