[2] 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.

For example, 1991's Blame It On My Youth, covered songs by Tom Waits ("Purple Avenue," aka "Empty Pockets") and Lyle Lovett ("God Will"), includes show tunes such as "If I Were a Bell" (from Guys and Dolls) and "On the Street Where You Live" (from My Fair Lady), and remakes "Trust In Me," from Disney's The Jungle Book, into a strikingly sultry and sinister song of seduction and death.

"[3] 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".

The song was later released on the Due South: The Original Television Soundtrack (1996) CD, and later by Holly Cole only on the Japanese compilation album Yesterday & Today (1994).

Following Don't Smoke In Bed, the trio released a CD entirely of songs by Tom Waits, called Temptation.

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.

[9] The album, produced by Cole and Greg Cohen, covers songs from Tom Waits ("Walk Away"), Gordon Lightfoot ("If You Could Read My Mind"), Mort Shuman ("Viva Las Vegas"), Captain Beefheart ("Love Lies"), a James Bond Theme by John Barry ("You Only Live Twice"), and a Cole original ("You've Got a Secret").

What we end up hearing on this record is the moment when we discover what we love about the song, and what its essence is for me.” Holly Cole isn’t one of those artists who falls into any one category.

Her smoky voice is sultry, her arrangements smart and sexy and all the while she and her musicians very uniquely reshape traditional Jazz, Pop and Country standards, this time particularly from the New American Songbook writers including Marty Balin, Peggy Lee, Hal David, Burt Bacharach and Johnny Mercer.

My mother crushed a grown-up aspirin into canned peaches that I ate, and then my father bundled me up and put me on his shoulders and we walked around the neighbourhood in the middle of the night.

And I could feel the cool, moist Nova Scotia sea air soothe my sore throat and rid me of my cough while I gazed from my father’s shoulders at what was my neighbourhood, but at night in the moonlight it looked like magic to me.

The simple structure of the song left it wide open to arranging ideas like extending the form and adding a variety of harmonies.

There’s a Lady on Stage [13] also featured Jane Siberry, Cherie Camp, Laura Hubert, Molly Johnson, Sarah McLachlan, Maggie Moore, and David Ramsden.

The special premiered on Global Television Network on January 5, 1993 and featured a concert taped at Brampton’s Heritage Theatre.

[20] Cole, along with Mary Margaret O'Hara, Ed Robertson, Serena Ryder, and Hawksley Workman performed in Christmas at the Concert Hall, a special hosted by Erica Ehm.