On a chilly autumn night, the Olympia Theatre became a sanctuary of sound as Gregory Alan Isakov took to the stage. The South African folk singer, renowned for his poetic lyricism, delivered a rare performance of energy and intimacy. Tinged with nostalgia, Isakov crafted a reverie of melancholy connection.
The evening opened with She Always Takes It Black, a devastating lament that immersed the audience in Isakov’s confessional style. His voice – a deep, warm murmur just shy of breaking – is indistinguishable from his studio recordings. It carries a fragile conviction that holds listeners in quiet awe. His excellent accompanying band, composed of his childhood friends, weave violins, bass, banjos, and drums into a captivating soundscape. Even his gentlest, acoustic tracks assume a delightfully dark, rock-tinged quality live – somewhere between Springsteen and Cohen.
Isakov’s setlist largely drifted between his celebrated albums This Empty Northern Hemisphere, The Weatherman, and Evening Machines. The Weatherman, a record inspired by his travels, carries a suitably wistful whimsy throughout. Amsterdam drew cheers, its meandering melody filling the theatre with longing. The night also featured the sparse desert textures of Appaloosa Bones, a stripped-back album inspired by West Texas.
Donning the trademark fedora that shrouds his face, Isakov performed much of the show cloaked in a wash of coloured light, moody darkness, and smoke. He stood in a solitude that matched the introspective tone and mystique of his songs. Though shy, Isakov is quietly witty and capable of building a rapport with his audience.
Conversations faded to silence as he played San Luis. The song is an evocative narrative of travelling through Colorado’s San Luis Valley, evoking embers of rural tranquillity. His lyrics are largely grounded in the natural world, yet are imbued with existential weight. Master & A Hound and Sweet Heat Lightning are both beautiful folk songs, but they almost serve as counterpoints in tone; one dark and dispirited, the other peaceful and soothing.
He sings of traversing mountains and plains, representing a personal journey from apartheid Johannesburg to Philadelphia to Boulder, where he now tends his organic farm. His music is the very essence of rueful Americana, halfway between home and the horizon. The timeless world of Isakov’s repertoire is full of wilderness, boundless skies, and hopeful adventure.
Midway through, This Empty Northern Hemisphere emerged as the emotional highlight. An exquisite violin and bass intro from Steve Varney and John Paul Grigsby gave way to a stirring instrumental climax. The song and album epitomise his early work – music that feels like looking to the stars on a dark winter night.
Conversely, ‘Southern Star’ and ‘Caves’ brought the lush, sweeping energy of a late summer evening, blending grandeur with urgency. This was fitting of Evening Machines, a Grammy-nominated album that fuses natural motifs with contemporary themes like anxiety and immigration. A brooding cover of Ron Scott’s Liars erupted into a cathartic crescendo.
As the night drew to a close, the band gathered around a single microphone and performed fan favourite, The Stable Song, beneath a solitary spotlight. The audience remained transfixed until the final chord faded, before exploding into applause as if waking from Isakov’s spell.
When he thanked them, it was with the humility of a man genuinely surprised by how far his songs have travelled. The final song came as a welcome surprise: for the first time in three years, Isakov played Living Proof – my personal favourite. The dreamy, nostalgic ode to youthful adventure was the perfect close to a magical evening.
Gregory Alan Isakov’s performance was a reminder that music’s greatest power lies in its warmth and soul, his voice glowing like a lantern in the shadows. As I stepped back out onto Dame Street, traces of his music lingered softly in the cool night air.
