Joe Gittleman described the band's approach to the album in an interview: "We really want to make a fun, upbeat record with a lot of cool ska stuff. Songs I look forward to playing at shows." Dicky Barrett added that the songs reflect his "skewed and slightly distorted look at our world and life in general."
The Bosstones announced that they were working on an album on November 4, 2008, via a MySpace blog with two songs, "The Impossible Dream" and "Next to Nothing" streaming on the page. The band announced the completion of tracking on July 29. On October 16, 2009, the band announced the album's title along with a free download of the song "Graffiti Worth Reading".