Holly Cole was born November 25, 1963, in Halifax, Nova Scotia, Canada, into a musical family — both parents were classical musicians and her brother studied jazz. She discovered jazz as a teenager and moved to Toronto in the 1980s to pursue performance, where she began singing in clubs and later formed the Holly Cole Trio with pianist Aaron Davis and bassist David Piltch.
Her music blends jazz roots with pop, cabaret, and standards, delivered with a sultry, ironic flair. She became known for creative reinterpretations of songs ranging from Tom Waits and Cole Porter to The Beach Boys and Elvis Presley.
Cole has won multiple awards, including Juno Awards for Best Contemporary Jazz Album (for Don’t Smoke in Bed) and Best Vocal Jazz Album (for Shade), plus international honors such as Grand Prix Gold Disc Awards in Japan and the Ella Fitzgerald Award from the Montreal Jazz Festival. She also received an honorary doctorate from Queen’s University.
Music
Christmas Blues (EP, 1989) – debut 4-song EP.
Girl Talk (1990) – first full album.
Blame It on My Youth (1991) – features eclectic jazz and standards.
Don’t Smoke in Bed (1993) – includes the hit “I Can See Clearly Now”; platinum in Canada.
Yesterday & Today (1994) – North American/Japan release.
Temptation (1995) – all-Tom Waits material.
It Happened One Night (1996) – live recording.
Dark Dear Heart (1997) – broader pop/jazz fusion.
Treasure (compilation, 1998) – collection of early Trio work.
Romantically Helpless (2000) – pop-leaning jazz.
Baby, It’s Cold Outside (2001) – holiday standards.
Shade (2003) – summer theme with jazz standards.
Holly Cole (2007) – self-titled studio album.
Night (2012) – a blend of covers and originals.
Steal the Night: Live at the Glenn Gould Studio (Live CD/DVD, 2012) – Trio reunion.
Holly (2019) – new studio work.
Montreal (2020) – live recording from boutique performances.
Dark Moon (2025) – latest studio album featuring ensemble arrangements.