Using California hardcore as a foundation, the group incorporated funk-metal and skatepunk into its sound, developing into something that functioned as edgy, post-punk frat rock -- it was speedy and occasionally stupidly catchy, with heavy, propulsive rhythms and positive, optimistic lyrics that stood in pointed contrast to their grunge-addled peers. Through constant touring and recording, as well as appearances at surfing and snowboarding concerts and in videos, Pennywise developed a dedicated following among post-hardcore punk audiences, and were positioned to follow Bad Religion, Green Day, and the Offspring into the modern rock mainstream, but internal problems, culminating in the 1996 suicide of founding bassist Jason Thirsk, prevented the band from being anything bigger than a popular cult band in the vein of NOFX.

Jim Lindberg (lead vocals), Fletcher Dragge (guitar), Byron McMackin (drums), and Jason Thirsk (bass) formed Pennywise in 1988, naming the band after the monster in Stephen King's cult horror novel It. All of the members attended the same high school in Hermosa Beach, California, where they were involved with both punk rock and surfing. Thirsk had played in a local hardcore band called PMA, while the other members played with several other groups before the band actually came together. In 1989, they released their debut EP, A Word from the Wise, on Theologian Records. A local college DJ passed the record to Brett Gurewitz at Epitaph Records, and he signed the group in 1990. Pennywise's eponymous full-length debut appeared the following year. Pennywise became a word-of-mouth hit among the underground punk, surf, and snowboarding community, and the group headed out on its first national tour.

Six months after their debut was released, Lindberg left the group due to his frustration with its lack of motivation and the lack of security in rock groups. Thirsk moved to vocals and his bass teacher, Randy Bradbury, filled in on bass. Following his departure, Theologian released the previously unissued Wildcard EP, backing it with A Word from the Wise on its CD release. While he was separated from the band, Lindberg married, but decided to rejoin the group in late 1992. At the time, Pennywise were attempting to record their second album with Thirsk on vocals, and they were glad to have him back. During his time off, Pennywise had decided to focus on their career, and that increased focus was apparent on their second album, 1993's Unknown Road. Due to constant touring and appearances in snowboarding and surfing videos, the album sold around 200,000 copies. Before they recorded their third album in early 1995, Pennywise were courted by several major labels, which approached the band following the unexpected multi-platinum breakthrough success of Green Day and the Offspring. The band elected to stay with Epitaph and completed About Time, which was released in the summer of 1995. About Time became an indie hit, and the band's live shows became popular attractions. In particular, Dragge became notorious for vomiting on his audience, most notoriously on DJ Riki Rachtman at a show for the influential alternative radio station KROQ, as a veiled protest against the station.

As the band was preparing to record its fourth album in the summer of 1996, Jason Thirsk took a leave of absence from the group to try to control his growing alcoholism; Randy Bradbury again stepped into the bassist role for Pennywise, and he was scheduled to move to rhythm guitar once Thirsk conquered his addiction. Sadly, Thirsk was unsuccessful; on July 29, 1996, he committed suicide after a drinking binge. Pennywise were shaken by his death, yet decided to continue performing, adding Bradbury as a permanent member. The band's fourth album, Full Circle, was released in April 1997; Straight Ahead followed two years later. In fall 2000, Pennywise trudged on to release the live album Live at the Key Club, which was recorded at the tiny club in Los Angeles in front of a crowd of 600 fans on the band's previous tour. New studio albums followed in 2001 (Land of the Free?) and 2003 (From the Ashes). Pennywise had always been political and confrontational. But Ashes amplified those notions with its reaction to the volatile political climate in America on the eve of the 2004 presidential elections.

When Pennywise returned in August 2005 with Fuse, they were no less conscious of politics and society. But the album also returned to a more muscular sound, and included a few classic punk rock anthems for the kids to believe in. In March 2008, Pennywise released Reason to Believe on MySpace Records in the United States and Epitaph in the U.K. Fans also had the option of downloading the album for free, thanks to a partnership between MySpace, Textango, and the band. In 2010, vocalist Jim Lindberg amicably left the group, and it was announced that Zoli Teglas, the lead singer of Ignite, would become his replacement. After breaking in the new frontman for the next two years with constant touring of Europe, Japan, Australia, and the States, the seminal So-Cal punks returned to the studio for their tenth album, All or Nothing, which was released in spring of 2012. That year saw Teglas put out of commission by a back injury, so Lindberg rejoined the band. After touring All or Nothing, Pennywise got back into writing mode. Digging in the archives, they decided to freshly record some songs written years before by their late bassist Jason Thirsk, which were more positive and life-affirming than their usual angry political fare. The songs appeared on their next album, Yesterdays, released in July 2014. The group returned with another compilation album, Nineteen Eighty Eight in 2016; a compilation of some of their earliest material collected from early EPs.~ Stephen Thomas Erlewine