We placed a phone-call to Pepper guitarist/vocalist, Kaleo Wassman, where we spoke for about 45minutes discussing new Pepper music following Local Motion as well as new music from his other musical outlets in Sabotage Soundsystem and the Naughty Don. He was very excited about Pepper’s new No Shame Chardonnay they put out with The Wine Boss and took us down memory lane with the origin of Pepper’s name followed by their first major concert while living on Kona.
Below is a condensed transcription of our discussion. Enjoy!
Interview: PEPPER
The Pier: You guys have a rich history and I want to rehash the early days a little bit before we jump forward. So to start, what’s with the name? How did Pepper get its name?
Kaleo: We are 3 kids in High School in Kailua-Kona, Hawaii. We’re all waiters. We work waiting jobs, okay? And in Kona, especially back then, there are no other jobs that we could do where we could work for 3 or 4 hours and make the money that we did. Funny enough, though, we always use to get out of work around 10-O-Clock at night & then I would race home to watch Saturday Night Live. This was back in the 90’s when you had Chris Farley, Adam Sandler, Kevin Nealon, Dana Carvey, Mike Myers, Chris Rock and all of these All-stars. There was a skit that they kept re-doing and it was called The Pepper Boy. And basically its this Italian Restaurant and these Pepper Boys come up to the table, usually to a couple on an exclusive date, and they would come over and OBSCENELY crack pepper all over the woman’s plate. It was so funny to us watching the date get so angry and of course the lady just loving the Italian affection. It was one thing the 3 of us would talk about the next day in Bret (Bollinger) garage when we were rehearsing and we would just lose it.
So it’s 1997 and when we needed to come up with a name to play our very first gig, a graduation party at Kelly Campbells house, and we just knew “We Are The Pepper Boys” so lets just simply call it Pepper – And that’s how we got our name. [Haha]
Watch: The Pepper Boy SNL Skit
Oh, man that’s great! Sounds like you guys are going to have to get a music video going and re-enact that SNL skit…
I’m not going to lie to you, that’s exactly what’s going to happen. As soon as Local Motion 2 is ready, that’s exactly what’s going to happen.
And you guys came from Kona to San Diego in May of ’99 but prior to that, what do you remember about Peppers first big concert on the island and who did you play with?
Our first real jump into performing in front of people was at a graduation party & from there, we started gaining momentum and playing these bars and house parties. Anywhere we could play, we’d play. And by the way, Kona does not get musicians, especially back then. I think we had UB40 once in the 80’s & then nothing after that. Luckily enough though, in 1998, Shaggy & the Born Jamericans both came to Kona. This was when Born Jamericans album, Yardcore, was permanently jammed in my tape deck. It was on repeat, everyday, everywhere I went. So we were able to open for Shaggy & Born Jamericans and it was a 2 night affair at this place called the Kona Surf Convention Center. I think we got to open the gig by default just because there were no other bands at the time that was doing what Pepper was doing, in the loose vein of Shaggy & Born Jamericans. 
Wow! And before Covid shut everything down this year, I actually saw video of Pepper performing on stage with Edley Shine of Born Jamericans in D.C. You guys did a live version of the classic Born Jamericans song, “Yardcore.” What was that like?
Um, surreal! Its funny, because I’ve been doing this for so long and when you have a situation like that where Edley Shine comes on stage to do “Yardcore,” you feel like you’ve never been on stage before, that’s exactly how it felt. I was just in complete awe, and if you find any photos or video of that, you’ll just see me grinning from ear to ear the entire time. I get so excited when we have our special guests that can join us. Sometimes we can have KBong on stage with us, sometimes we can get Miles or Kyle from Slightly Stoopid, sometimes we can get Trish from Hirie. Whenever those kind of alignments happen, it just elevates the stage for us because its something new & its something different. It takes us back to those first days of being on a stage — Its that energy, that newness, that frequency of new sounds coming out, instead of the 3 of us just always pounding away like we have the last 20 years. So its nice & very special to have guests featured in any sense.
Since Local Motion & with Covid grounding everyone from tour, how has new music been coming along? Is there a timeline for new music from Pepper?
So March 9th was the last show date for Pepper. I think the world closed down on March 16th. We were booked, SOLID, for the rest of 2020 and then COVID hit. The entire script flipped and I have been in the studio recording multiple projects, multiple tracks & I have never had an opportunity to stay in one place for this long, since I moved here from Hawaii in 1999. I have been in my home in Oceanside since March 9th. I have been able to build an inventory for Pepper. I have a very mindful new release with Sabotage Soundsystem. There will be a Naughty Don album coming out, which is a production team that I started with some friends out of Los Angeles. And of course, right now, we are working on Local Motion 2 for Pepper. I’m only calling it Local Motion 2 as a working title, but we are already gaining tracks.
We’re working with Jungle Josh & David Foral, who produced “Brand New Day.” We’re working with Henry Fong & Jinco, who produced “Carnival.” We’re working with Noah Cronin, who produced the “Sugar” (808 Remix), which is a Naughty Don track actually. So we are in full swing as far as building up the inventory, right now. While we have our technology and while I’m able to work remotely with so many people, simultaneously, it has been an incredible eye-opener for me to at least take in full appreciation of the fact that for the first time since the 90’s, I’ve been in one place long enough to get to these projects. And when I’m able to, I will be playing all of these projects, LIVE, when earth finally re-opens.
Watch: Pepper – “Brand New Day”
I don’t know how you keep it all straight. You have Pepper, Sabotage Soundsystem and now the Naughty Don project. How do you prioritize what goes to which project?
The greatest thing that works for me is to not be hung-up or attached to the art. So if I get too attached to anything, then that thing becomes more of an anchor than a pair of wings. So the projects that I have that are in existence right now, if I just allow them to speak to me where they’re needing to go or where they’re wanting to go, that is super helpful for me to be able to share with my teams. I have a couple of teams that represent different parts of my music and all of the other things that I love to do. So I can rely on my counsel, I can rely on my teams to give me guidance and help me with those decisions as well when I need them. But for the most part, the art just allows itself to go where it wants to go. Its’ been very important for me to learn that un-attachment lesson because to tell you the truth, that’s not how I always thought or believed. I was always very, very attached and its almost crippling sometimes where the projects would not be able to breathe outside air. I would suffocate them because I was so attached. Now with releasing that, its been a different ballgame.
That brings me to Local Motion that we released. Local Motion was basically Bret & I writing songs to a click-track. We would come up with the key, we would come up with the melodies, together or separate, we’d come up with harmonies and we’d come up with a scratch guitar. Then we would send that off to these different producers, these different production teams to fill in and that took a lot of un-attachment for us. So basically, what the producers & the production teams were able to do is, think of a coloring book, we would allow them to have the black & white image and we let them use all of their sonics, all of their tricks, all of their gear to fill in that blank page, bringing that page to life. With that un-attachment lesson, it’s allowed me to implement that strategy into every other project that I’m doing. That’s why I’m able to really flow, and really build this inventory of music up.
And it looks like you’ve released one of those projects in Sabotage Soundsystem with Sabo 2 – How would you describe the intentions behind that record?
There is a lot of people affected by this quarantine and this whole new way of life, right? And what I have are these songs that I released back in 2018 for Sabotage Soundsystem and I’ve basically accumulated all of those into one project while additionally throwing on 6 to 7 other tracks, two of those tracks are actually produced by the Naughty Don. The project is called Sabo 2 and what I want it to be is a gift for some of those people having hardships. Whether its anxiety, whether its financially, whether its depression, I want to allow these people a simple gift and its available on Soundcloud, YouTube — its completely FREE! Of course if you have Spotify, Apple Music, Pandora etc, you can listen to it there as well, but I also want people to know that if you don’t have those platforms, you can have this music. I’m just hoping one of these songs can give you a break and take you out of the madness that may be going on in your life during these unique times. You can even download it for free from my own personal website, KaleoLive.com.
That is a gift & I see that in what Law Records put out with The House That Bradley Built. I mean you have more than 20 bands with 20+ songs in a stripped down setting covering Sublime. Pepper covered “Work That We Do” – How difficult or easy was it choosing a Sublime song to cover?
This project is the brain child of Law Records general manager, Paul Milbury. He came up with this idea, he approached the team with it and we all thought it was fantastic. So when Law Records was able to do this with The Nowell Family Foundation, and being such big Sublime fans, it was one of those things where its such an opportunity to get to play one of these songs we grew up with. Now was it easy to pick one? For me, yes, pretty easy. To tell you why, I don’t think you can pick a bad one [Haha]. There are so many good Sublime songs its really hard to narrow it down, but “Work That We Do” was very special to me because I first heard it in High School in Kona where you really couldn’t get music back then. I mean you could get Top 40 tapes and of course Yellowman, and Gregory Isaacs and all of the deep reggae cuts, but to find an album like Robbin The Hood, that was tremendously difficult. I had a friend who was actually able to get a copy and I remember sitting down in the parking lot at Taco Bell after soccer practice listening to it and just thinking how this is like a whole other level of music for me. “Work That We Do” is just something that always sat with me since I’ve heard it. I was excited to give it a different approach. I was able to work with the production team of Naughty Don through this because we were able to produce this all remotely. So when I sent them a guitar track, the production team was able to fill in the rest and give it the mix and the sonic that it really needed. It became one of my favorite songs I’ve been a part of in 2020.
Watch: Pepper – “Work That We Do” (Sublime Cover)
So you released Sabo 2 on August 26th, what are the plans for new music moving forward? When can fans expect new Pepper music?
So Sabo 2 dropped on August 26th. Then there is the project called The Naughty Don that’s going to drop a cover of Sublime’s “Ruca” on 11/20/20. Then on 1/8/2021, we’ll release the first Naughty Don single, “Easy” with the album release of Naughty Don’s Electric Beach on 2/26/21. And then we will be able to probably wrap up Local Motion 2, again that’s a working title, by Thanksgiving or the first part of December. We’ll probably drop new Pepper sometime in 2021.
That’s exciting and you know we haven’t really heard much, publicly, about the Naughty Don. How would you describe the Naughty Don? Who is and what is The Naughty Don?
If you go to my website at KaleoLive.com & if you go under Projects you’ll be able to see a description of what or who the Naughty Don is. I would really encourage people to go there and check it out so they can read about it. It is a project that continues to evolve and continues to get better and better. On this Sabo 2 record, you’ll be able to hear 2 Naughty Don remixes–one of which is a secret Pepper track that was actually benched from the album, No Shame. It was benched in the American releases but it was released overseas, especially in Japan & Australia. It’s called “The Whistle Song.” The funny thing is the Pepper version will be completely different. So if you find that, then you’ll be able to do a side-by-side comparison and see how the Naughty Don’s frequencies are a bit different when it comes to this genre of American reggae.
Pepper has been making a splash, so to speak, the last few years in the Wine community putting out some award winning wine and I understand you now have a new Chardonnay that’s dropped?
Pepper has been making award-winning wine the last 2 and a half years. The San Francisco Chronicle wine competition, 2 years in a row, we’ve gotten Silver, Gold & Bronze for all of our wines. And yes, we just launched our new wine called, The No Shame Chardonnay. We’re not licensing our name for the wine, we’re making this wine with Thomas Booth, also known as The Wine Boss, and we have a partnership with him. We didn’t want to just license our name to the wine, we wanted to be active in the creation of it. And so its really incredible for us to get these awards and accolades because we are being able to co-create this wine with Thomas. And so this newest one, the Chardonnay, took us a really long time to approve cause I’m not really a Chard guy. So when this Chardonnay came into our existence it really was incredible. 
How many different wines does Pepper have out, now?
So we have our Original Blend, but it sold so quickly that we had to shelve the last 3 cases. We will re-release that when we feel that its at its peak and that’s going to be in a couple years. Then we have our Blend 2 which took Gold at the San Francisco Chronicle competition for 2019. Now we also came out with a Malbec, we have a Cabernet called In With The Cab, which is a play off our album In With The Old. All the bottles have these Pepper artworks that fans will be able to see and even though they’re not the exact album art, the elements of the albums are there. So we’ve been able to use this Pepper art on these bottles and bringing that kind of art to the wine. Now we have a No Shame Chardonnay.
I love how you pair different wines under the theme of different albums. Like: “Hey, I want to grab a bottle of Chard, drink a glass while listening to ‘No Shame’ & see how it pairs together!” As one might do with wine & cheese.
That’s EXACTLY what we want. We want you to put on the album, crack open some wine and really tap into how you feel in that moment. Try not to think of the past, try not to worry too much about the future, just how do you feel at that moment when you’re drinking the wine and pairing it with the music?
That is wonderful and I have to ask, with the inventory of music going up and up, as you described, in addition to being so collaborative with different producers & production teams, can fans expect any collaborations on new Pepper?
Oh, absolutely. How about this, because at the top of the conversation we were mentioning Edley Shine of Born Jamericans. I was lucky enough to have an opportunity to record a track, which its working title is called “Moon Demo” and of course that’ll be changed, but it has been such an honor to be able to do something with Edley Shine. To have a track that the production duo of David Foral & Jungle Josh brought, this heater, and we were able to build it up and write it out and it has seriously become one of my favorite jams on Local Motion 2, as of now. I would say that its exactly the evolution of what I want to do sonically with the positivity of this genre. I would say it is so important for us to always remember how influential straight Jamaican reggae is. I think with all of the projects I have going on right now, my baseline is straight old school Jamaican reggae. And the whole reason behind it is without Jamaica, without our brothers & sisters in Jamaica, without any of that, we would have none of the bands we have in the states right now. They are the absolute roots of this genre and I will continue to bring them forth in awareness for anyone who is willing to listen to the music that we make.
So with that said, and for those who don’t know who Edley Shine is, how would you describe him in terms of his style and how it lines up with you on the “Moon Demo”?
So I encourage everyone to go, right now, to their Spotify or whatever their musical platform is and listen to the album, Yardcore by Born Jamericans. Edley Shine’s frequency has been neglected for way too long. He really does bring this BASS, and I’m not just talking bass as in a sub-woofer, but like a foundation with this frequency through his voice. Working with him and how my voice frequency is so different from his, however, be able to work in harmony together in that state is a reason why this track is so important to me.
We look forward to hearing that & Local Motion 2 in 2021! Thank you so much for the time, Kaleo. I really enjoy talking music with you and hearing your passion & positivity regarding all of it. Is there anything you’d like to leave the fans with as we wrap up?
I would like to say something that has helped me in this time of quarantine. If someone finds this useful, awesome, but I’d like to share that I’ve allowed myself to be a little more kind to myself. That in turn has helped me to be a little more kind to other people. I’ve been noticing with this awareness of kindness, its really softened the harder edges that I was experiencing before I was aware. So it really is a cool thing to be a little kind to yourself. Allow yourself that kindness. Watch what it does to the person next to you and then watch what it does to the person next to them. I think kindness is probably the one thing that has really become available for me to use as a tool during this entire process of a new pandemic world. I just hope that if you are having anxieties or some fears about anything, try that really simple practice and I hope it can soften some of the harder edges that you may be experiencing.
And also, just one side-note too, I’ve been a fan of The Pier for a really, really long time. I just wanted to say thank you! Thank you so much for all the work that you do, all of the interviews that you do, everything that you’ve always done for us. I will always look towards The Pier and especially to you, Mike, as far as a marker of gratitude. Thank you for doing what you’re doing and allowing a platform for us to speak on. I really appreciate it and I appreciate you!
Related Links:
Pepper Website
Kaleo Wassman Website
Law Records Website
The Wine Boss Website
Interview By: Mike Patti