The septet was originally comprised of Obi Fernandez (vocals/trombone), Jesse Hayes (drums), Cory Williams (guitar), Thad Merritt (bass), Rich Graiko (trumpet), Gideon Blumenthal (keyboards), and Josh Cohen (sax). They released two independent albums, 2002's Searching for a Melody (re-released in 2003 on Megalith) and 2004's Five to Two, before a demo tape made its way into Tim Armstrong's hands at a hometown Transplants show. Armstrong was impressed by the music, soon asking the guys to guest on the forthcoming Transplants album, Haunted Cities.

Westbound Train continued touring and over the years shared stages with bands like the Toasters, Reel Big Fish, the Skatalites, Street Dogs, the Planet Smashers, and more. They also scored a 2005 Boston Music Award nomination for Best World Music Act, the only ska outfit to be given the honor. By early 2006, their friendship with Armstrong had turned into a record deal with his Epitaph imprint, Hellcat Records, and Westbound Train's label debut, Transitions, was issued that September. Williams left the group after sessions for the album were complete to pursue a jazz career, and the band soon welcomed guitarist Johnny DeCarlo into the fold as his replacement. ~ Corey Apar