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Since forming in Kailua-Kona, Hawaii, in 1997, Pepper has become one of the most popular reggae-rock bands on the scene. Members Kaleo Wassman, Bret Bollinger and Yesod Williams have been traveling the world for more than two decades, releasing seven studio albums along the way, and performing everywhere from sold-out amphitheaters to surfing competitions to low-key, hyperlocal festivals. And while plastic cups filled with beer usually litter the place at these joints, on the Pepper tour bus, wine has long been the drink of choice.

In the fall of 2017, Thomas Booth, a winemaker and the owner of Wine Boss wine bar in Paso Robles (and a longtime Pepper fan), approached the band with an idea to make a wine using the cover art of Pepper’s most popular album, Kona Town. It didn’t take much for the trio to embrace the wine business: Less than a year after the band’s initial conversation with Booth, Pepper Kona Town wine is a fixture onstage at every show—and with the creation of their second and third releases, the band have become regulars at the Paso winery as well.

Following the success of the original 75-case run of the Kona Town Red Blend 2016, the band has just released a 2017 Red Blend “2”; now more tuned in to the winemaking process, they sourced only organically grown grapes from the Clarksburg area (the wine is Certified Green by Lodi Rules), decided to limit oak influence to neutral barrels, and put out a blend of 60 percent Petit Verdot, 30 percent Cabernet Sauvignon and 10 percent Cabernet Franc. A 2017 California rosé is also available, and the wines now ship to 35 states, though the brand continues to gain fans locally—and converts among fellow reggae-rockers. “What we’re doing with Pepper wine is a grassroots type of movement,” Booth told Wine Spectator.

Wine Spectator assistant editor Lexi Williams spent time with the trio during a recent concert in Coney Island, Brooklyn, to talk about the band’s humble wine roots, first “oh yeah!” wines and grand plans for wine to conquer the alt-rock scene.

Pepper at the Ford Amphitheater at Coney Island Boardwalk in Brooklyn; photos by Cheyne Dean/Voyage in Veil Photography

Wine Spectator: How did wine come to be a staple on your tour bus?
Bret Bollinger, 38, bassist-vocalist: Oh man. We got into wine a long time ago. There’s obviously great cuisine in Hawaii, and we kind of cut our teeth just [working in restaurants]. The tourists would come in and try all these different wines. We learned a lot about wine and wine pairing. We all kind of fell in love.
Yesod Williams, 38, drummer: I worked at Roy’s [the flagship location of chef Roy Yamaguchi’s Hawaiian-fusion restaurant chain] for years on the Big Island. We all know what we’re talking about when it comes to wine and what good wine is.
Kaleo Wassman, 40, guitarist-vocalist: It was like the most important luxury that Pepper could always kind of afford, because no matter what, there’s always a price range that it would fall into.

Wine Spectator: What are your personal wine tastes like?
YW: We started out with reds, but as time has gone on [we got more into whites]. My favorite white wine is Ramey Chardonnay. That shit is like—it almost coats the whole inside of your mouth. I found out about Ramey in ’96, when I was working at Roy’s. It was the $150 bottle of white. Someone would order Ramey, and you’d be like, “Oh yeah!”
KW: My go-to is actually Chile. Chilean Cabernets are one of my all-time favorites. Also, I was in Portugal for about three weeks … [for] a little surf trip. It was the first time that I’d ever had a Vinho Verde. It was the most incredible, effervescent white wine that I’ve ever had. It was so delicious with all the seafood that they served.
BB: I like Old World wines. It could be because I spend so much time in Europe—I’ve lived in Spain part-time for about the last five years, and I have a home that’s almost done there in Madrid. I like [wines] to have a lot of personality. I love Bordeauxs. I love Riojas. I like a Chianti. I’m getting into Malbec a lot too.

Wine Spectator: People might not necessarily associate your kind of music and lifestyle with wine. What would you say about that?
KW: The one thing about that is that I’m really interested in wine. I’ve always been a firm believer in making sure that you fill your own cup before you try to fill anyone else’s. What we’ve done here with Thomas [Booth] is kind of really special. It seems like every single one of our peer [bands] have launched a beer—311, Rebelution, Sublime, Dirty Heads. We’re kind of like the only band in our genre that is spearheading wine.
BB: It doesn’t seem like it would go, but it absolutely does. I think it can enrich and invigorate certain types of music. Do I want to go see Slayer and drink wine? Maybe not right off the top. But do I want to see Maynard [James Keenan] and Tool or Perfect Circle? I do! Especially because he’s so invested in wine culture and his journey with that.
YW: Some people think like, “Oh, band guys are going to make a wine.” And then they’re like, “Holy shit, this is actually good.” And then they’re like, “Wait, I didn’t mean it like that!”

Wine Spectator: What’s the next step for Pepper wine?
BB: We’re excited to have quality wine. We took the time with [Booth] up there in Paso Robles to enjoy it and, you know, take it nice and slow. We’re not just unleashing a bunch of wines on people. We’re tasting and tasting and tasting until our teeth are red.
KW: We want to make it accessible. If you are able to help a novice and get them willing to try it, that’s fantastic. For people to just enjoy, and then think, is what I want. Sometimes I listen to a song and I just enjoy it. I don’t think about it. I’m not even listening to the words, I’m not trying to figure out what key it’s in or what the tempo is or who’s it by.

I’d say our three-year plan is to make sure that our wine is at every festival that includes this genre. I’m talking a huge presence, like our own parties and after-parties. And just make it fun, make it a lifestyle, because that’s what it is.

The ambition runs pretty rapid, so now it’s like, what’s next? [In five years], a destination concert festival for our wine with bands in our genre, maybe that is in multiple places. The Warped Tour just got done, maybe we’ll take over. The Wine Tour!