Internationally renowned jazz singer Holly Cole is set to grace the stage of Nanaimo’s Port Theatre on September 13, 2025, to share her latest album Dark Moon, which dropped January 24, 2025.

With a sultry voice, complex arrangements, and transformative takes on classics, Cole has become a multi-platinum artist with a number of awards—including two JUNO Awards, two Gemini Awards, and two Japanese Grand Prix Gold Disc awards. Cole was the fifteenth winner of the Ella Fitzgerald Award, joining the ranks of previous recipients Etta James, Aretha Franklin, and Sade.

“I wanted to see the big city and I’m really close to my brother, so I wanted to see him. But I had no idea that I would be swept off my feet,” Cole says. She knew all about classical music—both of her parents were musicians and she had grown up playing piano—but jazz was a world unknown to her.

Hearing the intensity, witnessing the culture, and how much people gave themselves to the genre, Cole fell in love. It had complex elements that were familiar to her, but it was subversive, rebellious, and incredibly exciting to a teenage hitchhiker.

What really appealed to her was that, as she put it:

The foundation of jazz is the spirit of improvisation.

Before reaching the studio, musicians prepare extensively. There’s usually a time limit, either with the physical space or the availability of the artists. Instruments are often recorded separately, either for technical reasons or to accommodate collaborators.

Holly Cole is no stranger to substantial arranging before a recording session herself. Jazz is a feeling, but it’s one that is built upon tangible components and learned skills.

For Dark Moon, Cole broke from the standard. To harness the spontaneity associated with jazz, this new record was recorded with every artist in the room, collaborating as partners.

“I was happy, lucky, and thrilled about that,” Cole says, a twinkle in her eyes.

Her ensemble includes Davide Direnzo on drums, John Johnson on the saxophone, and George Koller as the bassist—plus a number of other incredible accompanists. She describes this band as her dream team, cherry-picked from previous collaborations.

For six years, she released music as the Holly Cole Trio. The first member is obvious. The other two were David Piltch on bass and Aaron Davis, who has returned to play piano on Dark Moon. Although the ‘Trio’ was dropped from their label in 1995, Cole continued seeking musical partnerships.

The album covers New American Songbook artists like Marty Balin, Hal David, and Peggy Lee. When it comes to curating the tracklist, it’s not just about which songs Cole likes or which ones she could sing well. It’s also about whether or not she has the right group of people to record it with.

For Dark Moon, the stars aligned.

Cole’s music thrives on minimalism. “I love when people have a moment to digest—to digest the lyrics, to digest the music,” she says. Her band members know that.

Although it’s her voice on the record, hers is not the only one that matters. Part of the joy of having great collaborators at her side is listening to them and allowing them to be major contributors themselves. Her band members come with their own creativity and musicality, and she welcomes their individuality.

“I felt comfortable enough to go into the studio, what you might say, underprepared,” Cole says.

The fourth track, “No Moon At All,” categorizes the moon as an interloper. Rather than inspiring lovers, its light intrudes on their desire for intimacy. Famously covered by Aretha Franklin, Frank Sinatra, Andy Williams, and originally performed by Audrey Hepburn, “Moon River” is recognized across generations. Cole was not attracted to the song’s familiarity; she was drawn to how the moon symbolized adventure, a love of what's to come. The moon is commonly viewed as a romantic or maternal figure, but Dark Moon explores what other roles it can fulfill.

The original titular “Dark Moon” was first recorded by rock singer Dorsey Burnette, but was then rerecorded by country singer Bonnie Guitar in 1957. In yet another genre-bending move, Holly Cole has transformed it into a jazz track.

Cole didn’t originally know how to produce music. Over the years, she’s familiarized herself with the technical side of making music and has grown as both a vocalist and collaborator. She’s a best-selling Canadian artist who could release songs at random and have them sound technically beautiful.

But what really matters is the pull and weight of a song—what it means to her, and what else she can bring out of it. Part of understanding the record is getting to know the person behind it.

She recalls an early memory of being on her father's shoulders.

“I was maybe three or four years old … My dad and my mom both woke up because I was coughing with this terrible cough,” Cole describes. She had croup, an infection of the upper airway, causing a bark-like cough. Her mother crushed aspirin into peach cans, and her father wrapped her up in a cocoon of blankets. He carried her outside into the Halifax sea air to clear her throat.

At four in the morning, the neighbourhood was empty, and the only sound was of her father's footsteps. Atop his shoulders, she was that much closer to the shining moon. She went to bed that night with a secret, a vision that none of her friends yet shared.

“I was so little, and I had never seen the night before,” Cole says. “Ever since, the night and the moon have been a muse for me.”

Holly Cole plays jazz to make connections—she found it by crossing the border to see her brother, after all. She's performed at venues across the world, including Aeolian Hall (London, Canada), Blue Note Tokyo (Tokyo, Japan), and Goethe-Theatre (Bad Lauchstädt, Germany).

“The bigger the places I play, the more I miss the small places,” Cole says.

The atmosphere of the theatre is driven by the people in it, and the audience brings out something new in each of Cole's performances. The more intimate the venue, the clearer the communication between the stage and the seats becomes.

Between the audience, the band, and herself, there's a give and take that Cole adores. Performing has always come naturally to her, which is why she's extended herself beyond just music. She appeared in the short film “The Fairy Who Didn't Want to Be a Fairy Anymore” (which premiered at the 1992 Toronto International Film Festival), featured in an episode of Due South, and has pursued some theatre as well.

She embodies the fluidity and freedom of her music, even in her speech alone. “In both disciplines, whether it's singing or theatre, you have to access a part of you that's real,” Cole says.

When reimagining songs, Cole looks for the subtext. In her arrangements or vocals, she suggests or implies something beneath the surface. A tone, an idea. Holly Cole explains, “It could be any number of things, but … when [listeners] hear my subtext being really real to me, they'll find—especially if I leave them space—they'll find a place for it to be real to them.”

Since the beginning, her dream, though big, was simple. To play live with some of the greatest talents in music. “Honestly? That's what I'm doing,” Cole says.

After 12 years, Holly Cole returns to the Port Theatre in Nanaimo on September 13. Tickets are available now for $75.