Taking their name from an early band joke about writing a concept album that meshes with the 1973 Disney Robin Hood cartoon in the way that Pink Floyd's The Dark Side of the Moon supposedly meshes with The Wizard of Oz, Sherwood formed in late 2002 while its members were students at Cal Poly State University. Originally consisting of singer and guitarist Dan Koch, bassist Nate Henry, and guitarist Chris Armstrong, the group was completed with the addition of drummer Joe Greenetz and keyboard player Mike Leibovich. The band's self-released debut, 2004's The Summer EP, and an opening slot on the Vans Warped Tour that summer caught the attention of pop-punk label SideCho Records, which signed the band later that year. Sherwood's full-length debut album, Sing, But Keep Going, was released in May 2005. Touring came next, of course, and the guys logged time throughout the year with bands like This Providence, Tokyo Rose, and Daphne Loves Derby. Armstrong exited in early 2006 to return to school, as the band's profile steadily grew thanks to the support of popular news blog, AbsolutePunk.net. Sherwood (now a quartet) eventually inked a new deal with MySpace Records that fall and released A Different Light in March 2007.