Each of the band members had played in other bands in the Hermosa Beach, California area and attented the same high school. The group signed to Epitaph Records in 1990 and released Pennywise in 1991; the album quickly spread throughout the punk community, earning the band some nation-wide recognition. Lindberg left the band soon after the debut and Thirsk took his place on vocals, with Randy Bradbury taking Thirsk's place on bass. Lindberg married but returned to the group in 1992.
With Lindberg back, Pennywise released Unknown Road (1993), which was an underground hit and established the band as a force in punk music. By 1995, punk bands like the Offspring, Green Day and Rancid had hit the mainstream and Pennywise was invited to join several major labels. The band refused and stuck with Epitaph Records, releasing About Time in 1995; the album was another indie hit.
In 1996, Pennywise began recording their fourth album; Thirsk left to try and quit drinking; he was successful but then committed suicide after a relapse on July 29, 1996.
After Jason Thirsk's death, Full Circle (1997) and Straight Ahead (1999) were somewhat less popular than the last few albums. This was followed by a live LP, Live at the Key Club (2000) and Land of the Free (2001). After that came From the Ashes (2003).