Two of Pepper's three members started working together in 1996; that was when singer/guitarist Kaleo Wassman first joined forces with bassist/singer Bret Bollinger. After going through quite a few drummers in the '90s, Pepper decided that Yesod Williams was the best man for the job. With the Wassman/Bollinger/Williams lineup in place, Pepper left Hawaii for Los Angeles and went on to be an opening act for shows by Burning Spear, Shaggy, Eek-a-Mouse, Pato Banton, and other major reggae artists. Pepper first entered the studio in 1997 to record a seven-song demo, but by 1999 the trio was signed to the L.A.-based independent label Volcom Entertainment.
Pepper's songs appeared on various Volcom compilations, including 1999 Summer Sampler and The Early Poems Of. The threesome's first full-length album, Give'n It, was released by Volcom in 2000. The following year, Pepper produced a sophomore album, Kona Town, with Steve Kravac (who has worked with blink-182, Youth Brigade, Guttermouth, Less Than Jake, and other alternative rockers). Volcom released Kona Town in 2002, and In with the Old followed two years later, as Pepper continued touring with the likes of 311 and Snoop Dogg. The band also began its own record label, LAW Records, whose first release was a 2003 reissue of Give'n It. A live DVD was issued in early 2006 before the guys returned that fall with the studio full-length No Shame and a subsequent tour alongside Slightly Stoopid. Pink Crustaceans and Good Vibrations followed in 2008. In 2013 they signed with the Island label and released a self-titled album with production from former Faith No More and Train producer Matt Wallace. In 2016 they returned with the single "Start You Up" along with the album Ohana. ~ Alex Henderson, Rovi