Debbie Underwood paints the version of Montreal we want to believe in

You don’t need to be from Montreal to feel something when you see one of Debbie Underwood’s paintings. You just need to have been here once, late enough at night or young enough in spirit to believe that a bagel at 3 a.m. can be profound, that a corner deli can be sacred, or that the city's more than a crumbling heap.

Underwood paints that Montreal. The one without the orange cones, where Ben’s Deli is still standing, Saint-Viateur Bagel is postcard perfect. Her work is like a timeless summer day where the brickwork is warm, a winter morning of spiral staircases slick with ice, and off-frame people look like they just stepped out to grab a smoke or feed the meter.

Born and raised in Rosemont but now based in St. Thomas, Ontario, Underwood hasn’t lived in Montreal for years. But she never really left.

“Painting keeps me connected,” she says. “It keeps me connected with the people. I still have friends and family here, but I’ve also met so many others through the art. It’s amazing how many people I’ve gotten to know just because a painting reminded them of home.”

That idea of home—what it was, what it is, what it should be—sits at the heart of her Montreal series. Begun during the early months of COVID, when Underwood was living in Alberta, the series started as a personal project and quickly became something bigger.

“Once I was a few pieces in, I knew I had to show them in Montreal first. I didn’t want to sell the originals right away. I wanted them to come home.”

“I paint Montreal because I know it,” she says. “I feel it. It’s in me.”

Brushes and strokes

Returning to the city for her first solo exhibition, Coming Home, at Casa d’Italia in 2023 was a kind of full circle moment, decades after leaving she'd returned, and just a couple of years after surviving a massive heart attack that could’ve ended it all.

“I had a 100% blockage. A widowmaker. I was lucky to survive. Ever since then, I’ve slowed down. I only work a few hours a week as a barber now, and the rest of the time I paint.”

If her work has the feel of a love letter, it’s not because she’s looking at the city through rose-coloured glasses—it’s because she’s choosing to remember it the way it once made her feel. There’s no performance of civic decay in her scenes. No collapsing infrastructure or trucks that've cuaght fire on the side of the highway. But don’t mistake that for naïveté.

“I know the roads are a mess. I drive back often enough to see it. But I don’t want to paint that part,” she says. “Although I did think about putting a little orange cone in the corner of one just for fun.”

She laughs when she says it, but there’s something honest in that impulse: a quiet acknowledgment that what she’s doing might not be documentary in the strictest sense—but that doesn’t make it any less real. “People say to me, ‘You’re painting the places that are disappearing.’ But I don’t plan it that way. It’s intuitive. I see a photo and something grabs me—composition, colour, light—I just know when it’s right.”

“I paint Montreal because I know it”

There’s realism in Underwood's brushwork, but also impressionism. Detail, yes—but not without emotion. She works primarily in acrylic, using the medium’s fast-drying nature to layer crisp lines and saturated tones with precision. Her compositions tend toward frontal elevation—structures are rendered head-on, with little vanishing-point distortion, creating a flatness that draws attention to surface detail and spatial arrangement.

Lighting is even and shadow is minimal, suggesting a photographic source but softened through painterly modulation. And while her work engages in representational fidelity, it often omits clutter, decay, or signage noise—editing reality to heighten mood and visual legibility. It’s not realism for realism’s sake, but a constructed clarity that sits somewhere between rendering and memory.

“I guess I’ve developed a style,” she says, almost surprised by it. “People tell me they recognize my work right away. I never set out to do that. I just paint what I feel.”

It’s that balance—between feeling and form, past and present—that’s earned her a growing following. Prints and commissions now travel across Canada and the U.S., reaching the homes of expat Montrealers who want a piece of the city they left behind. And while Underwood’s artistic influences include Alice Neel, Georgia O’Keeffe, and the Group of Seven, her spiritual kin might be people like John Little or Carol Spandau—Montreal artists who chronicled the city as it shifted under their feet.

Still, Underwood’s version is uniquely hers. It’s what Montreal looks like when you’re in love with it, even if it broke your heart. Even if you had to leave. It’s a version of the city that lives inside anyone who’s ever called it home—even briefly.

And maybe that’s why it resonates. In a place where so much has changed—and keeps changing—Underwood’s paintings are a reminder that some things endure. If not on the sidewalk, then at least on canvas.

“I paint Montreal because I know it,” she says. “I feel it. It’s in me.”