Gregory Alan Isakov Torches Massey Hall in Toronto with The Milk Carton Kids [Photos]

There is something magical when Gregory Alan Isakov takes the stage and, for two hours, is able to transport you to another space, where all other distractions are removed, and you are alone, surrounded by quietness and serenity, and the occasional crowd chatter. It could not have been a more welcoming return to Toronto for this Colorado native, born in South Africa and raised in Philadelphia, a trained horticulturist, and who also runs a farm, in-between recording and touring.

It’s been five years since his first Toronto show at Danforth Music Hall back in 2018, and this time around, Gregory Alan Isakov and his gang of multi-instrumentalists, guitarists Steve Varney and Danny Black, violinist Jeb Bows, bassist John Paul Grigsby, and drummer Max Barcelow, bring a much more refined and resonating sound to Gregory’s back catalogue and his most recent album, Appaloosa Bones.

The stage was sparse, with the band spread apart and a large backdrop, projecting various imagery and illustrations of nature, landscapes, and cityscapes, juxtaposing with the music. Isakov opened the set, playing solo on banjo on “Before the Sun” before the band chimed in during the chorus. This was followed by the fitting, “Southern Star,” a track rich in imagery and metaphor, and instrument arrangements. “The Fall,” one of the standout tracks from Appaloosa Bones, is soaked in vulnerability but also a witness of resiliency as sung by Gregory. From the darkened crowd, some were singing along, “We all break a little, when we fall/ And everybody keeps saying, Get up, get up.”

Gregory didn’t quip too much with the crowd, but he did jokingly mention that the band safely crossed the Canadian border without the possession of any drugs on the bus. It wasn’t till mid-set that the set really grew on the crowd, starting with Gregory’s vocal prowess and harmonica playing on “Miles to Go,” followed by fan favourite “Big Black Car,” with Steve Varney’s banjo picking and Jeb Bows violin playing stealing the show. Isakov could very well play on his own, and the crowd would still be pleased by the end of the night, but it’s this camaraderie and long-lasting friendships between his fellow musicians that makes it special and a treat to see live.

Other highlights, Gregory dug deep in the archives to pull out “3 A.M.” from That Sea, the Gambler, playing solo to the crowd and standout title track, “Appaloosa Bones,” a testament to Gregory’s storytelling about being lost and finding human connection during the void. The set ended with “Caves” off the excellent Evening Machines album, where Gregory invited the crowd to sing along to the chorus, “Let’s put all these words away,” as he jokingly told the crowd, “until it gets awkward.”

As is tradition, the band came back on the stage for their encore, huddled together around a single microphone, playing “Amsterdam,” “One Day,” “Silver Bell,” and “All Shades of Blue” with the singers from The Milk Carton Kids. A surprised 2nd encore brought together best friends Steve Varney, and Gregory Alan Isakov for another fan favourite, “Stable Song.” Even though the show couldn’t have been at a nicer venue than Massey Hall, let’s all pretend it was underneath a beautiful night filled with stars because that was what it felt like. Nothing rushed, the heart filled to the brim.

“The Appaloosa Tour” continues with a batch of US East Coast shows with special guests, The Milk Carton Kids, before ending the year in the UK and Europe then Australia in the new year.

Gregory Alan Isakov (w/ The Milk Carton Kids) at Massey Hall (Toronto, ON) on October 16, 2023

26 photos