Formed in 1992 as a power-pop trio with a heavy punk influence and a fixation with Pez candy, Less Than Jake metamorphosed into a ska-inspired punk band with the addition of several members from 1993 to 1995. Vocalist and guitarist Chris, bassist Shaun and drummer Vinnie were the first incarnation of the group, based in Gainesville, Florida; after Shaun became the group's roadie, however, he was replaced by Chris (and later Roger). During 1993-94, the group added saxophone players Jessica and Aaron plus trombone player Buddy. Less than Jake debuted in 1994 with the album Pez-Core, on Dill Records. Losers, Kings & Things We Don't Understand and Greased followed until the group signed with Capitol for their major-label debut, 1996's Losing Streak.
Hello Rockview followed in 1998. The group also control their own record label, Fueled by Ramen. In fall 2000, the band released Borders & Boundaries, as well as landing the opening spot on Bon Jovi's North American tour.