Holly Cole: Jazz-Pop's Cool Canadian Voice

Chapter one: the cool arrives (1990–1993)

Cole emerged from Toronto's club scene with a trio sound built on space and irony: standards and pop songs delivered with a raised eyebrow, behind-the-beat phrasing, and a rhythm section that swung like a secret. The breakthrough records — Girl Talk (1990) and the platinum Don't Smoke in Bed (1993), with its beguiling cover of "I Can See Clearly Now" — made her an international jazz-pop star and proved the formula: jazz credibility, pop accessibility, and a persona entirely her own. She wasn't singing the standards so much as winking at them — and audiences adored the game.

Chapter two: the Waits turn (1995)

The audacious masterstroke was Temptation (1995): an entire album of Tom Waits songs recast as smoky jazz-noir — her sensibility and his songbook revealing each other as natural allies. Critics swooned; the album became a cult classic and reintroduced Waits' writing to a whole audience. It remains one of the great tribute albums by a Canadian artist — not imitation, but translation.

Chapter three: the long, stylish career

Cole never chased trends; the trends kept finding her. Through records like Dark Dear Heart (1997), Shade (2003), and steady international touring, she refined the signature: cool but never cold, ironic but deeply musical, equally at home in a Tokyo jazz club or a European festival stage. She became Canada's premier jazz-pop export — the artist audiences in a dozen countries associated with the country's particular strain of sophisticated song.

Why she matters

Holly Cole matters because she expanded what Canadian jazz-pop could be: not revivalism, not crooning nostalgia, but smart modern art with a pulse. Before the retro-cocktail wave, before the standards revival became an industry, Cole had already staked the claim: the songbook belongs to whoever brings the most personality to it. She brought plenty.