Gregory Alan Isakov Is on the Road

You can drive in any direction from Gregory Alan Isakov’s home base of Boulder.

You can go east into the unending flatlands and enormous skies of Kansas. Or west into the mountains, winding over Loveland Pass or shooting through the tunnel below. Go south through Navajo reservation land and into the unforgiving New Mexico desert. Go north into Wyoming, where the gray grasslands surrounding Laramie resemble the surface of the moon. On both I-70 and I-25, it’s not difficult to tap into a peculiar mindset particular to driving — that of being simultaneously still and in motion, of being in the landscape without ever really touching it.

The road is a powerful thing. Without it, Jack Kerouac and Neal Cassidy would have had nothing to write about, Easy Rider would be a rather short film (likely with a cheerier ending), and a defining piece of American mythos and self-definition simply wouldn’t exist.

Providing musicians with inspiration and giving Thelma & Louise a plot probably wasn’t high on the list of Dwight Eisenhower’s motivations when he signed the Federal Aid Highway Act of 1956 into law, but it nonetheless did exactly that. Joni Mitchell wrote her marvelous 1976 album Hejira during several cross-country drives made with companions, as part of Bob Dylan’s Rolling Thunder Revue, and completely alone (riding behind truckers and without a driver’s license, no less).

The trope of the American troubadour has proven romantic and resilient, having adapted to contemporary life’s constant connectivity and image-consciousness by way of hashtag-vanlife and hashtag-roadtrip Instagram influencers rather than be quashed beneath it.

If you’re a touring musician without access to Led Zeppelin’s infamous private plane, your relationship to the road is already a necessary and functional one. But for Isakov, as with Mitchell before him, it’s an artistic one, too.

“A lot of traveling makes it into the songs, into the writing,” says Isakov. “I constantly have my satellite out.”

Isakov, who plays the new Mission Ballroom on August 11, has leaned into the contemporary-troubadour image in recent years; the video for 2018’s “San Luis” features him traversing the Great Sand Dunes in his Volkswagen Vanagon (lovingly nicknamed Squeaky and now running quite happily on its second engine). “I use it for work. I use it for everything,” he says of the vehicle.

Then there’s the music itself. “I got my change behind the bed/In a coffee can/I throw my nickels in/Just in case I have to leave,” Isakov sings on “If I Go, I’m Goin.” Recurring themes and potent imagery include carnivals, California, sunsets, the sea, the Sangre de Cristo mountains, the train stations he claims to know too well. From the beginning, the singer-songwriter has possessed a keen sense of the ephemeral and of the psychological landscape found between motion and stasis.

One side effect of all this? Isakov’s fundamental appreciation for stability, for regimens and routines, for staying in one place. It helps that he has a working four-acre farm in Boulder, where he grows a variety of vegetables for nearby restaurants — and, it bears mentioning, raises a herd of Katahdin sheep he calls the T-Swift pack.

“Time is such a trippy thing when you’re working on music. You’ll work on a piece of music for a month, and it might end up in the trash. With farming, I grow for a bunch of restaurants, so it’s like, I have deliveries three days a week; I’m planting every week,” he says. “With recording, you have no idea. Months go by of work, and we don’t even know if we have anything. It’s a beautiful thing to be like, ‘I know what I can do in an hour.’”

And months do go by. He says he’s no perfectionist, but he’ll throw out months’ worth of work if it lacks true feeling.

“You can work really, really hard on something and then take a minute away and come back and realize it doesn’t really make you travel,” he says. “Some things you do in five minutes, it’s right there, and it worked on you.”

When I reach Isakov at his parents’ apartment in Philadelphia (they’re not home, but they’ll catch up with him in a few days), he’s fresh off a set at the Newport Folk Festival. He’s thrilled with the experience — festivals, he says, are a nice break from the more isolated work of normal touring, and he gushes about sitting in (and playing a Ringo Starr song) with Hiss Golden Messenger and The Tallest Man on Earth at a night show in a local church.

But there’s little Isakov won’t gush about: collaborating with the Colorado Symphony (“a wild bucket list” item), his younger brother and sometimes collaborator (“a fucking killer songwriter”), Leonard Cohen (“His live records are incredible. They’re just as good as his studio records”), playing Red Rocks (“Every time, it blows my mind”), Paul McCartney (“I’m constantly blown away by his writing”), and the 1985 charity single “We Are the World” (“I learned about music from that song. I was like, ‘Who is this blind piano player?’”).

Add to that list the “spacey country” record he’s working on in his barn studio between long stints on the road and work on the farm.

“I’m really excited about it. It’s a really simple barn recording I’ve been working on for a few months,” he says.
And true to troubadour form, the album will arrive when it arrives.

“I don’t have a deadline on it,” Isakov says calmly. “I’m waiting for it to finish itself.”

On Sunday, August 11, Gregory Alan Isakov plays the Mission Ballroom, 4242 Wynkoop Street. Get tickets at missionballroom.com.