Pepper moved to San Diego county from Hawaii in 1999, taking up residence in Carlsbad, Vista, and then Oceanside. “You’d be surprised how many Hawaiians live in Oceanside,” says guitarist Kaleo Wassman, a Hawaiian transplant himself. “Why Oceanside? Because I can afford to live on the beach here and still buy food.”
Wassman says he and his two other bandmates in Pepper chose San Diego because “this was as far away from home as we could afford to go. In 1999, all three of us decided to move from Kona to Carlsbad. We had a friend with a spare bedroom who lived there. Our first night in California, we all went to Tijuana. You wanna talk about culture shock? Going from a small island in the Pacific Ocean to Tijuana in one day — we said, what did we do?”
He says they picked up the San Diego Reader and scanned the listings of venues and local shows to get an idea of the lay of the land as far as the local music scene. “Our first gig was at a sushi bar in Carlsbad. They paid us in all-you-can-drink sake.” Soon after, Pepper began to land gigs at ’Canes and Winstons. In time, they forged a musical alliance with a local band likewise influenced by Sublime, Point Loma’s Slightly Stoopid. “Same attitude,” says Wassman. “Same work ethic.”
The duo that would eventually become Pepper started when Wassman and Bret Bollinger began playing together in middle school in 1996. They found a drummer named Yesod Williams, left Kona for San Diego a couple of years later, and once here hooked into the reggae circuit.
They eventually landed a deal with Volcom Entertainment and began working with Matt Phillips of Silverback Management (Slightly Stoopid, Fishbone) in 2003. Phillips took "Give It Up" -- originally released in 2002 -- to KROQ.
"It was similar to 'Date Rape' by Sublime," says Phillips. "That song was around for three years until it took off [via radio airplay]."
"He's the man," says Pepper drummer Yesod Williams about L.A. DJ "Jed the Fish," who got his station (KROQ-FM) to play the reggae/rock trio's "Give It Up." That airplay spurred other stations across the country to play the song, which in turn launched a label bidding war over the band (which includes guitarist Kaleo Wassman and bassist Bret Bollinger).
"There were, like, five labels," says Williams. "Columbia, Interscope, Maverick...we went with Lava/Atlantic because they only release, like, 13 records a year. Capitol releases, like, 300." Lava gave the band a three-album deal.
"Nowadays, no one gets huge advances," admits Williams. "But we're happy with the deal, to say the least." In 1999, they released their debut CD Give’n It on Volcom Entertainment.
Pepper began playing as many as 220 shows a year as tour support for acts such as 311, Flogging Molly, and, by 2001, Warped Tours. “That means you’re in the studio during your three weeks off,” Wassman says. The 2007 Warped Tour included Pepper and fellow locals As I Lay Dying.
Their self-titled sixth full-length was previewed in May 2013 by a single for "FKARND," whose title is license-plate-ese for “fucking around.”
At home, Wassman says he hits open-mic nights at clubs in Carlsbad and Leucadia. “There are these amazing bands in San Diego that nobody knows about.” For eats, he favors the Hill Street Café, and then there’s the ocean. “When we’re home, we surf every day.” He had been in the water on the day we spoke by phone. “Sixty-seven degrees,” he says of the ocean temperature. “No wetsuit needed. Just being by the ocean is incredible,” he says. “Oceanside’s got a lot of grit, but I kinda like that. You got soccer moms, bikers, surfers. It’s got so much in this one little zone.”
Pepper spent January through June, 2015 recording its album Ohana. “We just acquired the old Pennywise studio last year,” says Wassman about the Hermosa Beach space where they laid down the tracks.
“The new album is just us three with our original reggae rawness using the arrangements we’ve learned over the years,” says Wassman. “It was recorded with just the three of us, and Mike Sutherland who co-produced.” That back-to-basics album was released in April 2016 on Pepper’s own Law Records label, which also releases music by Santa Barbara’s Iration and Baltimore-based Ballyhoo, preceded by the single “Vacation.”
In 2018, Kaleo Wassman launched a new line of wine, in a partnership with Masters Kitchen chef Darrell.
The reggae trio landed on top of Billboard's Reggae Chart in Autumn 2019 with their 8th studio album, Local Motion, ousting Soca Gold 2019 from the top spot and from the top 10. The album features nearly a dozen guest players.
Their song “Work That We Do” is the lead single off a September 2020 compilation, The House That Bradley Built, featuring never-released acoustic covers from the catalogue of the late Bradley Nowell’s band, Sublime, performed by more than 20 bands. Performers include G. Love, Pepper, HIRIE, The Expanders, Common Kings, The Skints, Long Beach Dub Allstars, and Trevor Young (SOJA). Descendents contributed an ukulele rendition of their song “Hope,” a song Bradley covered on 40 Oz. to Freedom. Reggae star Half Pint performs his song “Lovin’,” which was the original sample for Sublime's “What I Got.” Jim Lindberg of Pennywise donated a cover of “Boss D.J.” and a duet of The Melodians’ classic “Rivers of Babylon” (Sublime Acoustic: Bradley Nowell & Friends) is sung by Bradley’s son, musician Jakob Nowell, and Bradley’s father, Jim “Papa” Nowell. Proceeds from the album helped fund the Nowell Family Foundation's opioid recovery facility, Bradley’s House.