Farm To Stage: Acclaimed Singer-Songwriter Gregory Alan Isakov Talks Two Passions

Gregory Alan Isakov released his excellent album Appaloosa Bones in August 2023 — the Boulder, Colorado-based singer-songwriter’s first studio LP in five years following his Grammy-nominated 2018 record, Evening Machines. Despite his success as a musician, Isakov has continued to work at his another passion, growing things and running a working farm outside of Boulder.

JamBase had the chance to talk with Gregory about Appaloosa Bones as well as his ever-important work in providing people with food and the balance he’s struck between his two passions.

“Balance” is a tentative descriptor for Isakov’s work in music and growing because they exist at opposite ends on the see-saw of his life.

Music and growing also occupy the same space in Gregory’s world, entangled by the arrow of time. Gregory explained when asked what he sees as the similarities between farming and music.

“Well, I love [music and growing] because they could not be more different,” Isakov said. “They have a lot of similarities in a sense because they both take a lot of time and a lot of quiet to get right.

“Being a grower is kind of a trippy thing because you’re like, ‘How many more chances am I gonna get to grow tomatoes from seed?’ If I’m lucky, maybe 30 more times, I don’t know, 40? I don’t know. And it’s very similar with a blank piece of paper. How many times am I gonna get a chance at this one piece of music?

“We’re constantly seeding throughout the season. And I know seeds germinate at 78 degrees, 99% humidity. We put them in there. They pop in like 48 hours every time. It’s the same every time. And I’ll go into the studio for like three months, and I might not have shit.

“Time is the most elusive thing in music. On the farm, it could be like, ‘I have three hours. I’m going to flip this many beds. I’m going to replant this. I’m going to harvest this. I could probably get that washing thing done and bag that thing.’ And then with the studio it’s like, ‘Well fuck, I just spent months in there and I don’t even know if I got anything.’”

Isakov’s interest in horticulture was in a sense a catalyst in setting him on the road to becoming a successful musician as he followed his passion for growing to the artistic hotbed of Boulder, Colorado. Born in Johannesburg, South Africa, Gregory immigrated with his family to the United States where they settled in Philadelphia.

When it came time for college, Isakov’s interest in horticulture brought him to Naropa University in Boulder. Tibetan Buddhist teacher Chögyam Trungpa founded Naropa in 1974 and asked poets Allen Ginsberg, Anne Waldman and Diane di Prima, along with composer John Cage, to found a poetics department for the university’s first summer session.

All three poets were associated with the influential Beat generation, with Ginsberg one of its towering figures. Ginsberg, along with Waldman, decided on the name Jack Kerouac School of Disembodied Poetics in honor of Ginsberg’s friend and fellow lauded Beat writer. A lover of words and writing, Naropa’s association with the Beats, as well as its Buddhist foundation, also attracted Isakov.

“That’s why I came [to Boulder] in the first place, because I was really into the Beat poets when I was in high school,” he said. “I loved Ferlinghetti, but also On The Road, Jack Kerouac and stuff. But I didn’t really get it. I didn’t understand it. It was sort of just jumbling words, but there was something cool about it to me. And then I remember when I grew up and I read that stuff again. I was like, ‘Nope, still jumbly’ (laughs). But I still like it.”

Words are important to Isakov. His album Appaloosa Bones — a nod to Denver live music locale Appaloosa Grill where Gregory performed as a rising artist — is a masterclass in wordsmithery. Take the record’s sixth track, “Miles To Go,” for example. The impact comes not only in the visual the first line creates in the mind’s eye, but also how it is presented in a temporal sense.

“I see music as very visual,” Isakov said. “And so if there’s a line that happens, and then another killer line right after that, I’m sort of like, it’s not good because I don’t have time to live in that first line.

“So I need something very plain for a little while, and that sets the tempo of visually where you are in the song. But those first lines, ‘hotel bar/sinking in/broken hearts/busted strings.’ I was a little bit shy, to be honest.

“I was like, ‘Can I say this?’ Is this too, I don’t know, obvious or something?’ It was almost too sober and direct that it made me uncomfortable and I liked it (laughs). I like feeling a little bit uncomfortable about that. I remember that feeling exactly.

“I went back too, and I was like, ‘I wonder if there’s a better word that opens the song there?’ But I don’t think there is.”

Along with lines that draw you into a song, Appaloosa Bones also possesses a spacious, expansive, atmospheric sonic aesthetic, which feels very Western. The record could soundtrack a postmodern Western film a la Jim Jarmusch’s Dead Man. That feel seeped into the songs as Isakov wrote some of them while on a trip with friends and songwriting partners in West Texas’ Big Bend National Park. But there’s another driver of the aesthetic — an other place, a magical place.

“There was a weird Western movie vibe to it that I started noticing. And I really liked it,” Gregory said. “It felt right because I think as writers we have this world that we write from and I think probably every song that I’ve ever written in my life has always come from this world that I’ve created or that I’ve lived in for a while.

“And the characters are nature and some of them are people, but it might be like a hundred people from real life is one person, or all of a sudden the clouds can talk and it’s almost like you’re inside of a book.”

As someone who is so close to the land and what it produces, it makes sense that nature shapes Isakov’s music. The two, music and nature, are so entangled that to Isakov, ever the astute observer of words, calling himself an artist is difficult, even dangerous.

“I realized, calling myself an artist — quote unquote — is a very dangerous word because my whole life we’ve been making art about life, about our life. Art is essentially… we do it after work, we’re thinking about it while we’re at work. On the weekends we can’t wait to pick up our guitars or paintings or whatever we’re doing.

“But then as soon as you identify, ‘Well, now I’m an artist.’ It’s like, fuck, that’s a lot of pressure to put on yourself. And that’s dangerous waters. Do you know what I mean?”

Stream Appaloosa Bones and find out where to catch Gregory Alan Isakov on tour below: