Although formed in 1992 as a power pop trio with heavy punk leanings, Less Than Jake steadily transformed into a ska-inspired punk band with the addition of a horn section. Vocalist/guitarist Chris Demakes, bassist Shaun, and drummer/lyricist Vinnie Fiorello formed the first incarnation of the group, which took root in Gainesville, Florida. After Shaun became the group's roadie, however, he was replaced by bassist Roger Manganelli, who picked up the instrument just to join the band. During 1993-1994, the group added its first horn player, Jessica Mills, 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, and the group signed with Capitol for its 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.

Nuhfer left the band after the album's recording (and later went on to join Gunmoll), and Less Than Jake found his replacement in ex-Spring Heel Jack horn player Pete Wasilewski -- though to avoid any name confusion within the band, the second Pete was dubbed JR, and remained JR even after the first Pete decided to leave soon after the 2001 Warped Tour. Over the years, Less Than Jake issued more 7" and limited-edition vinyl releases than most people can keep track of, so the bandmembers compiled some of their favorite tracks on one record for 2002's Goodbye Blue and White, named in honor of their original tour van. Anthem followed in 2003 on Sire; B Is for B-Sides was issued a year later, comprised of tracks that didn't make it to Anthem's final cut. The DVD retrospective People's History of Less Than Jake appeared a month later. The four-song EP Absolution for Idiots and Addicts was released in April 2006, with their next full-length, In with the Out Crowd, following a month later. The latter album's slicker, more pop-oriented nature received mixed reactions from fans. In 2007, Less Than Jake announced that they had left Warner Bros.; a year later, the group formed the Sleep It Off label and released GNV FLA, an album loosely based on (and dedicated to) their hometown. Their ninth album, See the Light, arrived in the fall of 2013. Their fondness for the EP format saw them release the seven-track Sound the Alarm in 2017.