Review: Gregory Alan Isakov at Astor Theatre

Gregory Alan Isakov at Astor Theatre
Monday, February 16, 2026

As the audience filed into the Astor Theatre on Monday night for the first of two consecutive performances by Gregory Alan Isakov, the stage was bathed in a soft blue light. With a rack of guitars strategically positioned on opposing sides of the stage, a piano sat left of centre, while an amplifier and stool were positioned to the right as a layer of stage fog lingered over the brooding minimalist setting. The scene lay in stark contrast to the bustling happenings in the crowded foyer outside, beautifully tempering the mood within the sold-out room.

Isakov has become a virtuoso of the down low. Having carved out a name for himself while touring with Kelly Joe Phelps, the Colorado-based singer-songwriter’s early self-released albums surreptitiously featured the likes of Brandi Carlile. Having first seen him perform in 2012 at the lauded California-based music series Sings Like Hell (which not only featured luminaries such as Jackson Browne and Emmylou Harris but also, over the years, showcased an array of emerging talents like The Avett Brothers, Gillian Welch, Damien Rice, and Jason Isbell), Isakov’s musical ascendance was self-evident. And, in sharing that night with multi-Grammy Award winner Lori McKenna, it turned out to be one of the most inflicting on-stage pairings the series had seen.

Not only has Isakov gone on to earn a Grammy nomination of his own, but he has also amassed an oeuvre of eight albums, performed and recorded with symphony orchestras, and entrenched himself on America’s National Public Radio. It’s no small feat given he also runs a boutique organic farm in the foothills of Colorado’s Rocky Mountains. Not only is Isakov’s songwriting infused with a rustic yet soulful introspection, but it’s also embodied with vivid imagery from the world he traverses. When you’re immersed in a Gregory Alan Isakov song, you can feel the soil beneath your feet and the cool mountain air on your face, and even though you know you’re likely to have your heart wrenched, you wouldn’t want to be anywhere else. That’s precisely what Monday night was like.

As Isakov emerged from the periphery and eased himself onto the stool, a single beam of white downlight pierced through the shadowy blue light that immersed the stage. Armed with an acoustic guitar, it wasn’t long before his laconic cascade of notes was joined by Isakov’s eloquent and seductive vocals to cut through the brooding lighting. After a beautiful performance of She Always Takes It Black from his 2013 album, The Weatherman, Isakov explained that back in the States he performs with a large band, but how he’s always wanted to do a tour that’s more like playing songs at his kitchen table. He admitted though, the thought of doing so had long terrified him.

With that in mind, Isakov then delivered a beautiful, inflicting, and fearless rendition of Southern Star, a song from his seminal 2018 album Evening Machines. Not that Isakov was left fending for himself. He brought along a couple of musical colleagues to join him at various points across the night. A pause at the end of Southern Star allowed Isakov to grab a harmonica and gave multi-instrumentalist Steve Varney the opportunity to seat himself at the piano. Varney chimed in on Miles to Go from his latest release, Appaloosa Bones, before the pair ventured back to 2009’s This Empty Northern Hemisphere for gorgeous renditions of Big Black Car and Light Year.

As Varney left the stage, Isakov swapped guitars and returned to The Weatherman for a rousing solo rendition of Amsterdam before welcoming his brother, Ilan, to the piano for Second Chances, a co-write by the pair off the same album. When Verney rejoined the brothers, the trio’s tempered musical atmospherics were on full display. With Varney on electric guitar and Ilan Isakov on piano, Words was followed by Isakov delivering a charming rendition of one of his brother’s songs, Desdemone. The two songs were about as instrumentally lush as the night got. Finding himself solo once more, Isakov reached for an electric guitar and proceeded to deliver an achingly beautiful rendition of a new song titled Good Grief.

One of the highlights of Isakov’s ‘big band’ shows in the States has always been when the entire ensemble cluster around a single condenser microphone to close out the show. As Varney rejoined Isakov, this time with banjo in hand, two beams of downlight cut through the wash of soft red light that had suffused the stage to reveal a vintage-looking Ear Trumpet microphone. Placed front and centre, the pair huddled around the microphone with their instruments for a breathtaking rendition of Isakov’s hauntingly beautiful San Luis. Hailing from the Grammy-nominated Evening Machines, the song is the zenith on an album of musical highlights. Filled with rustic imagery and inner longing, the song’s execution was underpinned by the pair’s gorgeous harmonies in a performance as exquisite and inflicting as any on the night. 

The much-anticipated The Stable Song was next on the set list. Explaining that he has never had a big radio hit, Isakov noted that this song had actually been played on the radio. He assured the audience that Varney can testify to that, having heard it while visiting the dentist in Louisville, Colorado. “And also at the bank,” the sideman was quick to add. Drawn from his 2007 album That Sea, The Gambler, it is not only the song that introduced Isakov’s music to the wider public but also remains as one of the highlights of his set. And with the orchestration and delivery perfectly serving the song’s intimate, wistful, and nostalgic aura, tonight was no exception.

With Ilan Isakov now back on stage, Isakov told the audience the trio had one song remaining but were going to slow it down and make it last. With Isakov on acoustic guitar, Varney on electric guitar, and Ilan Isakov on piano, the trio closed out the set with the intimate Sweet Heat Lightning from Appaloosa Bones. With a wash of electric guitar and keyboards getting the song underway, the orchestration subtly built around Isakov’s laconic strums before the accompaniment dissipated, leaving his gentle acoustic notes and hushed vocals to impeccably fill the room. And with that, the three musicians graciously accepted a standing ovation and quietly disappeared off stage.

Reemerging for an encore, Isakov picked up a banjo. With Varney on electric guitar and Ilan Isakov on piano, the trio delivered an almost sprightly rendition of Before the Sun before quietening the mood once more with If I Go. I’m Gone. Varney’s atmospheric electric guitar and serene vocal harmonies were as hauntingly beautiful as the song’s poignant lament. With Varney back on banjo, the trio hummed out the night with a final song from Appaloosa Bones, the tender Silver Bell. On a night when could have heard a pin drop in the audience, Isakov once again instilled the power and virtue of quiet persuasion.

BRETT LEIGH DICKS

Photos by Linda Dunjey