INTERVIEW: The Organic Nature of Gregory Alan Isakov
08/22 @ SPAC, Saratoga
**This review originally appeared in our August 2026 print issue**
Photo by Rebecca Caridad
“It's so important to leave with something that inspires you and keeps your creative passion going as a listener. Those are the moments that I'm always aiming for.”
Describing Gregory Alan Isakov’s music in just one word would be a near-impossible task. But, if you’re forcing me to try, which clearly you aren’t, I’d have to say ‘nomadic.’ Picture a twilight roam through the desert, wanderlust ripping at the seams. It’s as if Isakov’s songs have traveled the world, returning a little wearier, but a little wiser all the same. In some ways, they have.
The South African-born, Grammy-nominated songwriter resides in Boulder, CO, which is where I found him on a particularly balmy Friday afternoon. In a few short weeks, he’ll be trekking east to our neck of the woods for an immense performance at SPAC on August 22, backed for the first time by the Philadelphia Orchestra. Although he’s played in this format before — even releasing an album documenting his time with the Colorado Symphony almost exactly ten years ago — it’s still an awe-inspiring event for Isakov, especially compared to his normal singer-songwriter performances.
“I wrote all these songs in my kitchen and all of a sudden there's like 80 people on stage that probably know the songs better than I do,” he tells me. “I'm like the worst musician up there for sure. So it's pretty intimidating, but also inspiring and incredible.”
To prepare for such a gig may seem daunting, but for Isakov, it’s all about trusting not only the process, but the musicians behind him. Surprisingly, they typically only have one rehearsal together ahead of the show, making the performance that much more special. Audiences are truly witnessing something one-of-a-kind.
“It's been years of experience playing with symphonies to kind of figure it out,” he admits. “There's nothing robotic about [my music] — tempos change and the feel changes throughout the songs all the time, so we've gotten a chance to figure all those moments out along the way. There's still a trainwreck here and there, but that's what makes it human.”
That easygoing, organic approach can not only be heard in Isakov’s music, with his laidback vocal style gliding through dusty setpieces as effortlessly as the best of them, but also in other aspects of life. To use the ‘organic’ descriptor a bit more directly, it shows up in his day-to-day life as the operator of Starling Farm, a small market farm in Boulder County. Currently, they grow for roughly 75 CSA (Community Supported Agriculture) members and a handful of chefs from local restaurants. It’s a passion that’s been in Isakov’s life almost as long as music has.
“I went to school for soil science and agronomy. That was my track. Writing music was just what I did at night. I never thought I'd get to do that for a living, let alone with an orchestra.”
After taking a few courses in Boulder, he ended up studying on a farm in the northern part of Scotland where he fell deeper in love with horticulture.
“High school kids, or kids in college, they’ll ask me for advice about touring and the music business and all that stuff. And I'm the last person to ask about that. But if you're trying to run a market garden, I have a lot of advice. Other than that, don't listen to me,” he laughs.
It’s a humbling thing to hear from someone who has toured the world many times over, not to mention receiving a Grammy nomination in 2019 for Evening Machines. Despite claiming to not be an expert, he’s got plenty of miles under his belt, beginning his touring career at just 16 years old. For context, he’s 46 now.
“For me, [touring] is sort of a holy experience,” he reflects. “It's like a spiritual practice because I love writing songs and I love creating. Sharing the music kind of keeps me accountable for creating. Performing was something that was never really in my nature before. I'm one of those guys that doesn’t even like going to the grocery store. So being in front of people and performing scared the crap out of me. I'm still challenged by it and I like that about it.”
Philadelphia Orchestra Photo by Ironglass Productions
Isakov has built one of those quiet careers for himself, not concerned with fame or the spotlight, but with making music about little moments, on his terms. His last record, 2023’s Appaloosa Bones, was inspired by some time simply traveling around West Texas. Ten years earlier, he released the masterpiece The Weatherman, which is said to be inspired by that very profession, where “there’s a guy on television or on the radio telling us the future, and yet nobody cares.”
Those familiar with Isakov’s work know what I’m talking about. Whether it’s the quiet, contemplative nature of songs like “The Stable Song” or “Suitcase Full of Sparks”, or the broodier stylings of songs like “Caves”, it’s as if a poet’s work is coming to life, allowing those in the know to close their eyes and bask in it. When it comes to sitting down and writing, Isakov’s motivations are as organic as the rest of his life.
“I call them ‘curiosities,’” he tells me. “I'll just get obsessed with certain things, or subject matters and then I'll just dive into that world. I don't know why I get obsessed with them. It's sort of a mystery to me, the whole writing process. I have not mastered it. I don’t understand it. And I don't think I ever will. You're just holding onto the reins, seeing where the song wants to go and kind of working with it. It's a mysterious sort of craft in that way.”
On August 22, Isakov’s curiosities will be magnified to new heights through the power of the Philadelphia Orchestra. Conducted by Chris Dragon, the world-renowned orchestra has “long pushed the boundaries of convention in the classical music realm,” all while maintaining an inclusive, nurturing spirit in their region. Providing their expertise as the backdrop to artists like Isakov makes for a special performance. The transformation of delicate folk-leaning songs into pieces more grandiose and cinematic will be taking place right before our eyes and ears, keeping us grounded in the present, and providing an experience to truly marvel at.
“For me, a great show is full of what I call God moments — these moments when you're with a lot of people and you're listening to a piece of music and everybody sort of loses themselves at the same time,” Isakov says. “I love that. I live for that. Because it's annoying to go to a show, you know? There's all these people, you have to park, dinner is expensive, tickets are expensive now —- which is a whole other can of worms. And then getting there, it’s crowded, maybe you worked that day, and you have to wake up early the next day. So I feel like it's so important to leave with something that inspires you and keeps your creative passion going as a listener. Those are the moments that I'm always aiming for.”
