In 1983, Cole travelled to Toronto to seek a musical career. In 1986, she founded a trio with bassist David Piltch and pianist Aaron Davis. Offered a record deal in 1989, the Holly Cole Trio released an EP, Christmas Blues, that year, which featured a version of The Pretenders' "2,000 Miles," which has proven to be very popular. This was followed by their first full album, Girl Talk, in 1990. A succession of releases followed through the early 1990s. For example, 1991's Blame It On My Youth, covered songs by Tom Waits, Lyle Lovett, includes show tunes such as "If I Were a Bell" and "On the Street Where You Live", and even remakes "Trust In Me," from Disney's The Jungle Book, into a strikingly sultry and sinister song of seduction and death. Also recorded in this period was a reinterpretation of Elvis Costello's "Alison." In 1993, the trio released Don't Smoke in Bed, an album produced by David Was, which included a hit single cover version of "I Can See Clearly Now". According to Jeff Bateman and James Hale, "The video for the song was put into heavy rotation on MuchMusic and earned a Juno Award nomination for Best Video. The album went platinum in Canada, reached No. 7 on the Billboard Contemporary Jazz chart, and won a Juno Award for Best Contemporary Jazz Album, in 1994." In this era, she also had an acting role in Laurie Lynd's short film The Fairy Who Didn't Want to Be a Fairy Anymore.
Solo career
Following Don't Smoke In Bed, the trio released a CD entirely of songs by Tom Waits, called Temptation. This 1995 release also dropped the "Trio" from the label. Cole followed with two albums, Dark Dear Heart and Romantically Helpless, which veered further from jazz by introducing pop elements to Cole's sound. In 2001, she returned to the Christmas jazz roots of her first CD with Baby It's Cold Outside, which included "Christmas Time is Here", "Santa Baby", and the title track. Swapping cold for hot, she moved to a summer theme in 2003's Shade, this time reinterpreting Cole Porter, Irving Berlin, and The Beach Boys' Brian Wilson. The album was named Jazz Recording of the Year at the 2004 Juno Awards. Cole's album, Holly Cole was released in Canada in March 2007. It was released in the US in January 2008 and was followed by a US tour. Cole tours frequently, particularly around the holiday season, in Canada. She was also a part of the 1998 Lilith Fair tour, and her song "Onion Girl" was included on that year's live compilation album. In 2010, Cole contributed a track for the World Jazz For Haiti charity album, recorded at Number 9 Audio Group in support of the Red Cross disaster relief fund. The album featured Canadian artists such as John McDermott, David Clayton-Thomas and George Koller. Cole's first live DVD + CD titled Steal The Night: Live at the Glenn Gould Studio was released in Canada in February 2012. It was recorded live at Glenn Gould Studio in Toronto on August 11, 2011. The performance marks the reformation of the original Holly Cole Trio lineup with Aaron Davis on piano and bassist David Piltch, in addition to John Johnson, Rob Piltch and Davide DiRenzo. Cole's first studio album in five years, Night was released in late 2012 on Universal Music Canada. The album, produced by Cole and Greg Cohen, covers songs from Tom Waits, Gordon Lightfoot, Mort Shuman, Captain Beefheart, a James Bond theme by John Barry, and a Cole original. Cole toured in support of Night in 2012-13 to Canada, America, Germany and Japan. In February 2018, she released a new studio album titled simply Holly. Cole received an honorary degree from Queen's University in Kingston, Ontario in June 2014.
