Few voices in Canadian music are as instantly recognizable as Holly Cole’s. Smoky, expressive, and quietly commanding, the jazz singer has spent decades reimagining standards and contemporary songs with an interpretive style all her own. On March 27, Toronto audiences will have the chance to experience that voice live when Cole brings her latest tour to the Winter Garden Theatre.
The performance arrives in support of Dark Moon, Cole’s acclaimed 13th studio album released in 2025. The record continues her long-standing fascination with the New American Songbook, weaving together jazz, pop, and country influences through atmospheric arrangements and richly textured storytelling. With longtime collaborators Aaron Davis, George Koller, Davide Direnzo, John Johnson, and Kevin Breit, the album leans into ensemble playing that feels both intimate and cinematic.
Cole’s concerts have always been about more than simply performing songs — they’re about reshaping them. Whether interpreting classics or unexpected covers, she brings a sense of narrative drama that turns each performance into a kind of musical storytelling. Songs from Dark Moon, including the dreamlike “Where Flamingos Fly,” capture that spirit particularly well, offering moments that feel suspended somewhere between jazz tradition and modern interpretation.
The Winter Garden Theatre, one of Toronto’s most beautiful historic venues, provides an ideal setting for that kind of performance. Known for its ornate Edwardian design and intimate atmosphere, the theatre creates the kind of listening environment where every nuance of Cole’s voice — every breath and pause — can resonate fully with the audience.
For Toronto fans, the show also represents a kind of homecoming. Although Cole’s music has built devoted audiences across Japan, Europe, and the United States, she remains one of Canada’s most internationally celebrated vocalists. Over the course of her career she has released 13 albums, achieved multi-platinum sales, and earned numerous honours including two Juno Awards, the Ella Fitzgerald Award from the Montreal International Jazz Festival, and an honorary doctorate from Queen’s University.
Her catalog spans everything from her early breakthrough recordings like Blame It on My Youth to the Tom Waits tribute album Temptation and the long-running success of her hit interpretation of “I Can See Clearly Now.” Yet even after more than three decades on stage, Cole continues to evolve as a performer — and Dark Moon marks another chapter in that journey.
Holly Cole performs at the Winter Garden Theatre in Toronto on March 27, 2026.
Tickets are currently available through Ticketmaster and the venue box office, with prices generally starting around $49–$89 depending on seating section and availability.
More information and ticket links can be found here 👉 https://www.ticketmaster.ca
For fans of jazz, vocal storytelling, and timeless songcraft, this promises to be an evening where the music feels both nostalgic and newly imagined — exactly the kind of experience Holly Cole has built her career on.
Photo Credit: Rodney Bowes
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