Pepper began in 1996 when singer/guitarist Kaleo Wassman met bassist/singer Bret Bollinger in middle school. The duo was influenced by Hawaiian icons Gabby Pahinui and Israel Kamakawiwo?ole. The group struggled to find a drummer to be in the band, with Wassman stating 'we were going through drummers like a bottomless pit.' Wassman and Bollinger heard about a drummer named Yesod Williams who had gained success around their small town, and later met Williams at a party. The two convinced Williams to join the band, and with the trio in place, Pepper left Hawaii for San Diego and went on to open shows by Burning Spear, Shaggy, and other major reggae artists. Pepper first entered the studio in 1997 and recorded a seven-song demo.

In 1999, after gathering a local following on the Big Island, Pepper gained the interest of an independent, L.A.-based record company, Volcom Entertainment. Volcom produced and distributed the band's first release, Give'n It, which combined dancehall, reggae, hip-hop, and pop genres. With the success of Give'N It, the band landed a spot on the 2001 Warped Tour.

After extensive touring, Pepper took to the studio with Steve Kravac (Less Than Jake, MXPX) to record their second album entitled Kona Town, released in March 2002. With Kona Town, Pepper's sound continued to evolve, adding elements of an 'island sound'. The track 'Give It Up' was released as a single. Pepper continued to tour throughout 2003 and into 2004, including dates with 311 and Snoop Dogg, along with appearances at the annual Bob Marley Birthday celebration, San Diego's Festival 'Street Scene', and a U.S. tour with Slightly Stoopid.

In March 2004 Pepper released In With The Old, debuting at #35 on the Billboard Heat Seekers and #18 on the independent albums chart. The album was recorded at 311's completely analog Hive studios by legendary board master Ron St. Germain (Bad Brains, Living Colour, 311, Tool, Sonic Youth, Soundgarden), the album showcases a broader range of influences shared by the trio. The band used punk keyboardist/producer Ronnie King on In With The Old as well as their later album, No Shame.

Beginning on July 20, 2006, Pepper supported 311 along with The Wailers on their U.S. tour. In August 2006, Jagermeister announced that Pepper & Slightly Stoopid would headline the annual Jagermeister Musictour through December 2006.

The band released their fourth album (and major label debut) entitled No Shame on October 3, 2006. It features production from Nick Hexum of 311, Tony Kanal of No Doubt, and Sublime producer/ Butthole Surfers member Paul Leary. A music video was shot for the single 'No Control'.

On March 20, 2007, Pepper released To Da Max, their first compilation CD containing rare and B-side tracks.

Pepper appeared on all dates of the 2007 Warped Tour, toured with The Expendables and Passafire, on their 'That's Where I Wanna Be...' 42 stop tour from October to December 2007.

Pepper released a new album on July 22, 2008, entitled Pink Crustaceans and Good Vibrations on their own label, Law Records. The band toured across the United States in 2008 from March through April with Redeye Empire and Iration. A European tour in support of Flogging Molly followed, including shows in Germany, Sweden, France, Italy and more. From August 1, 2008 to September 6, 2008, the band toured the US on the Tailgate 2008 Summer Tour. The band is now touring with Slightly Stoopid and Sly & Robbie. The band also headlined the 'Law Records' tour in October 2008 along with Passafire, and The Supervillains. This was their first tour consisting of only Law Records bands. After a UK tour with Less than Jake, and a break in December, Pepper, Passafire, and The Supervillains will tour the Northwest to complete the first Law Records tour.

The Spring 2009 line-up of the Jagermeister Music Tour featured Pepper with longtime staples on the punk scene, Pennywise. Pepper returned to the Jagermeister Music Tour after a 2006 outing with punk-reggae rockers Slightly Stoopid.

Pepper released their new EP album titled Stitches on the 12th of October 2010. A single, 'Wake Up', from the album was released June 28, 2010 along with 'Mirror'. The band will be touring with 311 to promote the album. Pepper will also be touring on the 'Like a Surgeon Tour' with Shwayze, Pour Habit, and Brother Ali in the last quarter of 2010.