Before forming the trio that launched her career, Holly Cole sang solo in front of crowds numbering in the thousands.

To grab people’s attention, she belted out Christmas carols to passersby, at the corner of Toronto’s Yonge and Dundas streets.

“It’s loud out there,” she says. “It was a great way to learn how to project your voice.”

Fifteen albums and three decades later, the three-time Juno-winning jazz chanteuse with hundreds of thousands of records sold, will be performing at Flato Markham Theatre, Wed. March 30.

The Holly Cole Trio – founded in 1986 with bassist David Piltch and pianist Aaron Davis – released its first recording, Christmas Blues, in 1989.

“The trio was how we all cut our teeth… absolutely priceless. The core of who I am. It was bass, piano and voice, because we couldn’t afford a drummer. Because necessity is the mother of invention, it made us responsible for the rhythm of the music. We had to create new ways to make our music,” she says.

“It meant we had to stretch our instruments” – including physically thumping the bass.

Few might know, however, that she may not have needed a drummer after all. She actually plays the drums. “It’s a beautiful outlet. Nobody cares if I suck. It’s not as inspected as my singing is. I love it.”

Over the course of her career, it’s not been uncommon to hear the words “sensual and intense,” to describe her, and her music.

“For me, I’m a minimalist,” she says of her own style. “I really like slow tempos, and I really inspect lyrics and I really love subtext, the power of suggestion and the power of implying things.”

Attention began to really ramp up with her 1993 platinum-selling Don’t Smoke In Bed, which included a cover of I Can See Clearly Now (Johnny Nash’s 1972 hit). The album reached number seven on the Billboard Contemporary Jazz chart, and won a Juno Award for Best Contemporary Jazz Album.

Covers of singer/songwriter Tom Waits recur in her work, including 1991’s Blame it on My Youth, 2012’s Night, and 1995’s Temptation – an entire album of his covers.

“He’s also a minimalist. His lyrics are right for me because of the fact we share a lot of similarities, but we are different too. We’re both jazz influenced, champions of the underdog, sing about darker interesting characters. People ask me why I sing about sad characters, but actually they’re people who have triumphed in spite of the odds, who’ve not been dealt a great hand,” she explains.

“The differences [with Waits] make it interesting for me to reinvent the song. He’s an American, I’m a Canadian, he’s a man, I’m a woman – and he has a different voice.”

Greg Cohen, one of her producers, who happens also to be Waits’ brother in law, introduced the two via phone when discussing the 1991 song, Purple Avenue, she was to cover.

Cole, though “in love” with the tune, sought a workaround for lyrics from a male perspective (about face-shaving). Waits was instantly easygoing enough to make changes.

“It takes such a confident songwriter to be so free to say ‘do you have any ideas?’”

The new album in the works, which she won’t yet talk much about, will be produced by Russ Titelman, the three-time Grammy winner who has also churned out the hits of James Taylor, Steve Winwood and Eric Clapton.

In the nearer future, though, the March 30 show is planned as a fusion of nostalgia, indulgences, and treats.

“It will be songs that people love, a retrospective too… and stuff that’s never been recorded that we only do live. It’s a surprise for people.”

In terms of her own career’s retrospective, looking back over the course of a three decade career, she can truly say Life Is Just a Bowl of Cherries.

“I thought: ‘One day, I’m going to play live with the best musicians in the world’, and that’s exactly what I’m doing. And that makes me super happy.”