There are singer-songwriters and there are farmers, and then there’s Gregory Alan Isakov, who is almost certainly the first-ever Hollywood Bowl headliner to list his occupation as horticulturist/musician.
For Isakov, that unusual journey began when a boy born in South Africa in October 1979, whose family immigrated to Philadelphia in 1986, decided that a Tibetan Buddhist college in Boulder, Colorado was where he’d finish his higher education.
“I came out here for horticulture school, this tiny little college in Boulder called Naropa,” says Isakov, 46, on a phone call from his home and market farm in Boulder County. “It’s a Tibetan Buddhist college.
“I came because I was really into, like, beat poets and the writing program, too,” he says. “They have this Jack Kerouac School of Disembodied Poetics. In high school I was like, ‘That’s so badass.’”
He laughs at the memory and returns to his tale. After graduation, he worked on a farm in Scotland for a year, before coming back to Colorado where he managed farm in Lyons, Colorado, 40-odd miles northwest of Denver. During the fallow months of winter, he gigged around the northwest with no thought it would lead to anything bigger.
“I would do these little tours and I never thought it would do anything,” Isakov says. “I thought, ‘I want to go camping for free.’ Make enough to pay for the campsite and keep going.”
Then he made his first album, 2003’s “Rust Colored Stones,” on a few pieces of equipment in his bedroom.
“And it did OK,” Isakov says of that album, which was followed by “Songs For October” and “That Sea, the Gambler” in 2005 and 2007. “I thought, ‘Oh, wow, people might want to hear these songs,’ and it scared the [bleep] out of me. I wasn’t built for being on stage or anything like that.
“So I thought, maybe I should probably do this if it scares me this much,” he continues. “I should probably see what it’s about. So I would do that a little bit, come back, work the main season, and then hit the road again in the winter.
“I did that for many, many years, and then I started really getting more out of it than I thought I would.”
Eventually he’d saved enough to buy his own small farm, which today has two acres in production and five people working it, enough that he can book shows even during growing or harvest seasons if he needs to.
It is still, he acknowledges, an unusual path to the Hollywood Bowl or Radio City Music Hall or Wolf Trap and Ravinia, all of which he’s played – along with Red Rocks in his own backyard – on this late summer tour with orchestras backing Isakov and his band.
“I sort of happened really slowly,” Isakov says of the musical side of his working life. “I have kids coming to shows and they’re asking me for advice on the music business. I’m like, ‘You don’t want any from me. I’m maybe the slowest career of all time.’
“I mean, I’m like, ‘Get a really long name that no one can pronounce. Don’t have any choruses in your songs.’
“But then once in a while I’ll meet a kid who is like, ‘Well, I’m really into farming, and I just want to know how you do that with your other job,’” Isakov says. “And I’m like, ‘Oh, I have tons of advice about that.’”
In an interview edited for length and clarity, Isakov talked about working with orchestras over the past decade or so, why streaming services helped build a following, and how shyness onstage inspired him to cover Mazzy Star.
Q: This is your first headlining show at the Hollywood Bowl. Have you been there for anything before?
A: No. I’ve seen it in a movie, a couple of movies. But I’ve never actually been there. We’ve played the Greek and a few other places in L.A. We’ve done the Staples Center; we opened there. But yeah, I’ve heard incredible things about it.
Q: So let’s talk about orchestral shows. You played Walt Disney Concert Hall with the L.A. Phil in 2025. You did a live album with the Colorado Symphony Orchestra in 2016. How do these compare to regular shows with the band?
A: What’s interesting is how the show has evolved. We’ve been traveling with conductor Christopher Dragon for this whole tour, and that’s been a huge advantage because we’ve gotten to change scores along the way and arrangements along the way. Even most of the scores to strings and horns so we could be a little bit more fluid with timing.
It just sort of now feels like an extension of the band, which has been really fun for the last month or so of shows. That’s been really exciting.
Q: How did you first get the chance to play with an orchestra?
A: Honestly, it’s crazy to me. I mean, I was a horticulture major in college, and I was just playing music in my bedroom forever. The thought of even playing a sold-out show with just a band is mind-blowing.
My manager and I, every fall, we write down things that would be sweet to see happen in the next year. I remember one year we were like, oh, it would be so neat to play with an orchestra once. And I think she just asked the director of the Colorado Symphony Orchestra if she thought it would work. We tried it out, and it was so much fun.
I learned so much because at that time we had percussion parts written into the scores. And you know, playing with a band drummer, like a rock drummer, is very different than playing with a symphonic bass drum, snare drum, you know, very straight. So we were like, OK, that doesn’t work.
We’re figuring it out along the way. But there’s just these moments that I live for in any sort of venue that we’re playing, in any sort of environment, like the whole crowd sort of gets lost for a moment and you can kind of feel it happen together.
And I felt like that way almost the entire time with the symphony. It was a really cool experience. And I thought I’d like to feel that way again.
Q: So you’ve done this often over the last decade?
A: We’ve done mostly the band shows in our careers. I’ve done a bit of solo work as well last year through Australia and New Zealand. And then we kept getting offers to play with different national orchestras. They would come in, and we’d instantly say yes because it’s almost spiritual for me. I love it so much.
Q: Because of the need for arrangements, do the sets stay pretty consistent?
A: All of our scores have been written by two friends of ours. Jay Clifford, who has a band called Jump Little Children, and he’s from South Carolina. And Tom Hagerman, who is in a band called DeVotchKa, and he’s local to Denver. So we just write Tom and Jay every now and then and we write new scores to the new record.
So now we have like three records worth of material that we can choose from, which is really fun. And even interludes that we’ve written along with the band, because we do that a lot between songs, so it felt less like, “This song is ending, and now this one begins.”
Q: With those first three records, how did you get them out to audiences beyond your immediate tours?
A: I didn’t have a label or anyone helping me. It was just me and my friend Sarah, who I still work with now. I remember one day I just called. I was like, “Do people just call iTunes? Is that how it’s done? Like, is there a number?” I think there was a number. There was a guy named Nate. He was like, “Oh, OK.” Nate said I could get the banner on the iTunes page back then.
The girl at Pandora answered the phone and was like, “OK, send it to me, and I’ll give it to my boss.” It really sort of happened organically, and ended up doing really well on Pandora. I would sell merch at my shows at the time and I was like, “Why are you guys here? How do you even know about this?”
You know, little tiny places, and people would be like, “I heard you on Pandora.”
Q: I was wondering: Does the physical work on the farm help your other work as a songwriter and singer?
A: Yeah, I think it does tie in quite a lot. I’ve always loved writing and playing because it was something I did before work and after work, and it was this special thing. I think the time away from writing is so good for writing as well.
I think it’s a dangerous place to call yourself an artist. It’s a dangerous place for your art because all of a sudden there’s pressure: “Oh, I’m an artist. I can make art and it has to be good.” [He laughs] Instead of just living your life, going to work and making art out of this place of necessity. For me at least that’s the way it seemed to work the best.
I tried being a full-time musician. I played 250 shows for a few years in a row and I was miserable. I was so depressed. [He laughs] Just seeing the world from a van or bus or airports, and there was nothing to balance me out with actually working. So I went back to work, and I sort of went full throttle on Starling Farm.
Q: Is Starling Farm mostly produce?
A: Yeah, it’s produce and flowers. We do a couple of florists still. We’re always experimenting with other stuff like fruit, but it’s mainly mixed vegetables.
Q: I recently saw Noah Kahan play the Rose Bowl. And you’re opening some shows for Brandi Carlile and Zach Bryan this year.
A: I love Noah.
Q: You’ve done some work together, I think?
A: Yeah.
Q: I guess what struck me was the music you write, the music Noah and Brandi and Zach write, it’s got a human sound to it. It’s not all electronics like a lot of stuff. So I want to ask how you understand the appeal of this indie folk, indie country today.
A: I’ve wondered the same thing. And for me, it’s just like something [bleepin’] magical about seeing somebody take words and mix them with an acoustic instrument, or electric instrument, played with your hands, and make someone feel something. I think there’s just nothing like it.
If you can do that I think that’s [bleepin’] magic. And when someone sees someone and goes, “Oh, well, I could do that too,” that’s inspiring. That is really the magic in any art. Just understanding like, “Oh, that’s in me. I could do that.” It’s not out of reach, you know?
Q: There’s a humanness to it that’s special.
A: Yeah, there is. I first met Noah, my manager called and said “There’s a songwriter that wants to come visit you. Is it OK if I give him your address? He’s in town.” I said, “What’s his name?” She said, “Noah Kahan,” and I’d never heard of him.
We were packing CSA boxes. It was a Tuesday; we do our deliveries on Tuesdays. And this guy walked in and said, “Hey, I’m Noah. I just wanted to check out your studio and talk to you and say hi.” He offered to help and so he helped load CSA boxes into our van.
I was like, “This is where I record in the barn,” and I was showing him my little setup. I said, “Where are you playing? Maybe I can make your show?” He’s like, “Oh, I’ve got three nights at Red Rocks,” and I was like, “Oh, I’m so sorry I haven’t heard of you! [He laughs] Don’t take it personally, I haven’t heard of anything.” And then I listened to his record on a flight that week and I thought it was so cool.
Q: Which record was it?
A: It was “Stick Season.”
Q: The last thing I want to ask you is about your new cover of Mazzy Star’s “Fade Into You” with Sylvan Esso’s Amelia Meath singing with you. How’d that come about?
A: I was ready an article about Mazzy Star. I think because her partner [David Roback] passed away. I’ve always loved them. And they talked about this moment in Australia. They were playing the Sydney Opera House and she [Hope Sandoval] played the whole show in the dark, and the crowd was so pissed off.
I was like, I was made for this woman. [He laughs] She’s my absolute hero.
I just tracked it in about an hour, really bare bones, and worked on it for fun. A few months later, I called Amelia and was like, ‘What this needs is your voice.’ She took a few months and then sent it back when she was home, and then we mixed it over winter.
And then it just got into “Practical Magic II.” I’m about to go check out the movie tonight. So Amelia is texting me last week, “Did you hear about ‘Practical Magic II’? She’s like, “I read all the books. This is my favorite thing ever.” We were just so excited.