Trevor Hall developed an affinity for summery acoustic music, from the beachside ambiance of Jack Johnson to the leisurely stroll of Bob Marley. Having spent his teenage years at a boarding school for the arts, Hall dedicated his life to music upon his high-school graduation. He self-released Lace Up Your Shoes in 2004; two years later, the teenaged Hall prepared for his major-label debut with Geffen Records. The Rascals Have Returned, an introductory EP produced by John Alagía, featured a soothing mix of reggae, folk, and roots rock. Sales were slow, however, and Geffen dropped Hall from their roster in 2008.

Hall continued to tour, performing shows alongside the likes of Ben Harper, Matisyahu, and the Wailers. He also returned to the studio to record a self-titled sophomore album, which emphasized the artist's reggae influences upon its release in 2009.