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Chasing Songs, Drivin’, and Loving Every Mile

Interview with Elliott Callaway

Elliott Callaway’s music has a way of sneaking into your head after you listen to him. From singing his first solo in Alabama as a kid to making a name for himself on California’s central coast, his songs are honest, heartfelt, and full of stories that feel real. In his chat with SYV Buzz, Elliott opens up about the people, places, and moments that shaped his sound—and why songwriting has always been more about conversation than performance. And if you want to hear it for yourself, you’re in luck: he’s making his Mattei’s Tavern debut on Wednesday, March 25, from 5–7 PM and he’s paired up with Luna Hart Wines for the Winemaker Takeover.

SYV Buzz: Can you remember the first moment you realized music wasn’t just something you liked—it was something you were born to do?

Elliott Callaway: I’m not sure if I can remember an exact moment, but I sang a solo in the fourth grade for my school’s Alabama History play (I believe the song was “Swing Low, Sweet Chariot”) and I think that would’ve been the first time that I had been told that I had any musical ability, and I remember really enjoying singing and how it made me feel.

SYV Buzz: Growing up in Alabama, were there specific people in your childhood or early life who shaped how you see music or storytelling?

EC: My little brother was one of these people who picked up the guitar and just seemingly made it do amazing things from the beginning. (In reality he worked really hard at it, and I just didn’t really see all of the behind the scenes). I think he probably inspired me more than anyone to dive deep into music.

SYV Buzz: Did you ever feel out of place as a musician growing up, and how did that shape your artistry today?

EC: I feel like it provided an identity for me more than anything. I could kind of lean into it at a time when I wasn’t really sure who I was.

SYV Buzz: Many of your songs feel like conversations to me. Do you write with a particular listener in mind, or is it more like talking to yourself?

EC: On my first album, a lot of the songs were conversations with myself or imaginary conversations with a certain person, like the kind you have while brushing your teeth when you think of the thing you wish you’d said or done in a certain moment. I think I’ve recently started to write from a different perspective, and I’m trying to focus less on myself and more on what I see around me in my songs.

SYV Buzz: Your lyrics hold such feelings-What emotions do you find hardest to write about, and which come easiest?

EC: I’m open to writing about anything, it’s just finding a way to say it or play it that doesn’t come off as cheesy. On Hank, I’d like to think that I was writing about stuff that was difficult, but that I wasn’t trying to get anyone to feel sorry for me. That can be a tricky thing when one is writing music that is focused on themself.

SYV Buzz: Touring or performing can be thrilling but exhausting. What’s your favorite road story—the memory you keep close when things get tough?

EC: I don’t know that I have a single story, but I try to keep an attitude of you either have a great show, or a great learning experience. And the learning experiences usually come with something to write about, so that’s an added bonus.

SYV Buzz: Has living and performing in California inspired your music differently than anywhere else you’ve lived?

EC: I think the only reason I’ve been able to carve out a career in music is because I moved to California. I wasn’t very familiar with the professional side of things back in Alabama, and it was from watching so many others out here that were able to do it and learning from them that I’ve been able to find any type of success.

SYV Buzz: Do you have any mentors? Who has influenced your sound the most, and why?

EC: I’ve had many people throughout my life that have helped along the way, but Fred Walecki (former owner of Westwood Music in LA, worked on records with Eagles, Linda Rondstadt, the list is endless) has probably been the biggest help for me. He’s just an honest person who I can show something to and he’ll tell me straight up whether I’m on the right track or not. I think it’s very important to have someone who will tell me the truth about what I’m doing, as I can get very attached and defensive about my art, but I need to always have the ability to take constructive criticism and get held accountable for if I’m really doing my best work or not. Most people will tell you that what you’re doing is good, whether they really mean it or not. What’s good about Fred is he always means it, so when he says something is good, you know he’s not just saying it to make you feel good. When he says it needs work, it’s because it needs work.

SYV Buzz: We often ask this question, but I love it. So, if you could sit down with any songwriter—living or gone—for a jam session or conversation, who would it be, and what would you ask them?

EC: The answer would probably change day to day, but today I’d want to sit down with John Prine and just talk about his writing process and trade songs. I get such a kick out of his lyrics, and feel like I’m constantly hearing something that makes me think “How do you come up with this stuff?” It’d be nice to get a little insight on that.

SYV Buzz: Great Answer. We love John Prine too (in spite of ourselves). So, looking back, what do you feel is one of the biggest misconceptions people have about the life of a musician?

EC: I think the two most common misconception(s) I’ve seen are that people think you’re either born with musical talent or not…I believe that some people have a natural lean towards music (things like having a good ear, vocal timbre, etc.), but I think that ultimately being focused and working hard will outlast any of those things. Second, being a professional musician does not equal a celebrity-like existence. Getting home at 2:45am after playing to an empty or uninterested bar is a more common experience than you might expect. If you’ve done that, and you still feel like you’re the luckiest person in the world to do what you love for a living, then you’re probably on the right track.

SYV Buzz: Another great answer that hits home. So, has a song you’ve written ever surprised you—taken on a meaning you didn’t intend?

EC: My song “Drivin” is a fictional story that is supposed to be a take on the crazy old country western story songs that would have some tragic figure getting into extreme situations and so on and so forth. I do sometimes wonder how that song came to me, but I’m more just grateful that it did. It’s probably the song I’m most proud of, and my favorite song to play, and I’m always excited to see how an audience will respond to it.

SYV Buzz: We really enjoyed listening to your Drivin’ tune. Next on your SYV agenda, you’re playing at Mattei’s Tavern at the Winemaker Takeover (Luna Hart) real soon. Have you ever been to Mattei’s and if not, do you have any expectations, curiosities, or anxieties?

EC: I’ve played in the area quite a bit, but haven’t had the chance to play at Mattei’s, so I’m very excited to share my music with the guests there. My only expectation is that the drive up will be gorgeous, and that it will be a beautiful evening for music in Los Olivos.

SYV Buzz: It will be fun—all the locals love wednesdays over at the Tavern. So, where do you hope your music takes you in the next five years—personally, creatively, or even geographically?

EC: I’m currently able to make a living doing something that I love more than anything else. If in five years, I’m still able to say that, I’ll be really stoked. I hope that during that time I’m able to continue to write some tunes that mean something to me and the people that hear them and play them in places that I’ve never been to. I can’t ask for more than that, but I’ll always welcome more if it comes.

From fictional tunes like “Drivin’” to lessons learned from mentors and life on the road, Elliott Callaway’s music hits because it’s genuine, thoughtful, and a little bit reflective. Don’t miss the chance to see him live at Mattei’s Tavern on Wednesday, March 25, from 5–7 PM, soak up the wine-country weather, and let his singer/songwriter vibes become a part of your afternoon.

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See our complete list of upcoming music and wine events in the Santa Ynez Valley.