Formed in 1992 as a power pop trio with a heavy punk influence, a sense of humor, 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 Demakes, bassist Shaun, and drummer/lyricist Vinnie Fiorello were the first incarnation of the group, based in Gainesville, FL; after Shaun became the group's roadie, however, he was eventually replaced by Roger Manganelli, who picked up bass just to join the band. During 1993-1994, the group added their first horn player, Jessica, and soon after came trombone player Buddy Schaub. Right before their first tour, however, Schaub went to Europe with friends, so saxophonist Derron Nuhfer filled in for shows during his absence.

With various 7" releases under their belt, Less than Jake debuted in 1994 with the album Pezcore, on Dill Records. Losers, Kings & Things We Don't Understand and Greased followed on No Idea until the group signed with Capitol for their major-label debut, 1996's Losing Streak. The album was full of the band's wry, fast-paced brand of ska-punk anthems, producing such fan favorites as "Johnny Quest Thinks We're Sellouts" and "Jen Doesn't Like Me Anymore." Upon the album's completion, Jessica left to pursue teaching, and (ex-Slapstick trombonist) Pete came on board. Around this time, Fiorello also started his own record label, Fueled by Ramen, with friend John Janick. Hello Rockview followed in 1998, and spawned a minor college radio hit with "History of a Boring Town." In fall 2000, the band released Borders & Boundaries on Fat Wreck, as well as landing the opening spot on Bon Jovi's North American tour.