How Portraiture Gives Us Permission to Stare

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Published 6:30, FEBRUARY 6, 2026 Madonna in a Tulip Chair (2025) by Louise Kermode.

SAY AN ALIEN were to crash-land in some post-apocalyptic iteration of Canada and, for purposes of research, had available to it only a catalogue of our most celebrated paintings. It would likely—and ­reasonably—conclude that this has ­always been a luminous, desolate landscape, shorn of human life, verdant and virginal, practically terra nullius.

When the Group of Seven materialized in a still-­nascent Canada, they rose on the dubious promise of constructing a national artistic identity, one achieved through those mystical, romantic landscape ­paintings that depopulated the rugged North. Indigenous peoples, when they appeared at all, did so without any faces. And so, with the aggressive support of the National Gallery of Canada, appraised by the art historian Joyce ­Zemans in her 1995 essay “Establishing the Canon,” they succeeded in influencing “the entire country’s idea of what was Canadian about Canadian art.”

Voice of Fire (2017) by Ian Shatilla.

The Kingston Prize, in a sense, was created to ­rescue the form from its interminably faceless underpaintings. Founded by Queen’s University professor Julian Brown and his wife, Kaaren, in 2005, the ­biennial ­portrait ­competition does more than promote Canadian ­artists and offer them a chance at winning $25,000. It also vies to produce “a visual history of ­national life” by way of the country’s many faces. The twenty-year ­history of this prize’s finalists, archived in a handsome new coffee-table book published last March, offers ­context for the ­cultural and sociopolitical concerns of such faces in years gone by: Andrew Valko indexes the rise of ­social media in Personal Surveillance (2009); Ian ­Shatilla ­archives United States president Donald Trump’s first term in Voice of Fire (2017); Cambridge ­radiologist Kari Visscher documents the pandemic ­sacrifices of ­medical workers with Frontline (2023), in which she depicts ­herself in scrubs approaching sainthood.

Personal Surveillance (2009) by Andrew Valko.

In the immediate aftermath of our faces being ­mostly concealed behind blue polymer masks, it’s as good a time as any to celebrate and reconsider the value of handmade portraiture. Depending on where you stand, the human face has become either a digital ­playground or digital battleground. Your Instagram feed can now produce a diaspora of thousands of faces that uncannily resemble but are not quite Kim Kardashian, a “cyborgian” look best achieved through plastic surgery and Facetune. Artificial intelligence technologies, still largely unregulated, have so improved over the past few years that they can now counterfeit reality to alarming effect, and those slippery tools are now raking open fresh wounds in the arts. The latest Hollywood ingénue, positioned as “the next Scarlett Johansson or Natalie Portman,” is a twenty-four-year-old brunette beauty with large, sea-green eyes, a familiarly attractive face, and no physical form at all. The practice of looking has itself been compromised.

The pleasure of these portraits is that you have permission to stare. Despite the relationship between looking at a face and the ways it intensifies empathy, studies have found most people hold eye contact for just a few seconds before looking away shyly. These portraits eliminate the awkwardness of established manners and, in allowing us to stare without anxiety, reveal something of their subjects’ humanity; we’re able to fall in love, then, with their difference, with our similarities.

A Cup of Silence (2025) by Opeyemi Olukotun.

You can parse the language of a young Black woman’s distracted expression in Opeyemi Olukotun’s A Cup of Silence, for example, and consider whether her sullenness is at all related to the two empty chairs beside her. In Self, 32, you can peek into the Montreal kitchen of Taiwanese Canadian artist James Lee Chiahan (who is also a designer at large for The Walrus), and appreciate the soft square of light that falls across his face to spill into the hallway or how his style of dress and decorative impulses afford him a connection to a faraway homeland.

The top prize for 2025 went to the Waterloo-based painter Louise Kermode’s Madonna in a Tulip Chair. At first, it appears to be an arresting, almost nineteenth-century realist portrait of an ordinary elderly woman—the kind of painting that, by virtue of its detail (the hands are particularly breathtaking), could never be recreated with AI. Madonna, here, is in fact Donna Meaney, who, in her youth, was often depicted nude or semi-nude by the detached, erotic gaze of Christopher Pratt and, later, under the more probing, ambivalent gaze of his wife, Mary. Biographers have claimed that Meaney became Christopher’s mistress, and so Mary’s controversial Girl in Wicker Chair—the nude that Kermode’s portrait echoes and which Mary adapted from a photograph made by her husband—takes on a stranger valence: the wife staring at the mistress staring at her husband.

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Some four decades after she was last painted, Meaney’s presence in Kermode’s painting is quite different. Her chair is refashioned into a kind of throne. She projects a regal authority once reserved for grand-manner paintings of nobles and royals. But unlike the portraits of the era she’s referencing, Kermode has made no attempts at any of the pre-Facetune liberties that pandered to the vanities of those wealthy and phlegmatic patrons who, despite having everything, were still desperate to look taller, or younger, or more virile, or more chaste. “I’m wearing my own outfit—the clothes are from Winners, the earrings are from Joe Fresh, and my watch is from Shoppers!” Meaney told me gleefully at the ceremony this past November.

Frontline (2023) by Kari Visscher. Self, 32 (2025) by James Lee Chiahan.

Instead, there’s something moving about Kermode’s choice to paint Meaney exactly as she is. The effect is not only of a self-possessed, seventy-something muse being released from the zoological gaze of idealization that caused so much discord in her youthful life. It’s a reminder that every portrait is also a self-portrait. What we have is a sixty-one-year-old painter, still in the tender beginnings of her career as a full-time artist (she retired from her administrative role at the University of Toronto in 2024 and recently trained at the Academy of Realist Art), reflecting on her own mortality, on the knowledge that most of her life is now behind her. In our era of relentless self-curation, of eye creams and deepfakes and the time-worn obsession with youthful prodigy, it’s refreshing to search for the beauty in the real thing: the graceful wrinkles of an aging face, the deep grooves of the neck, the wear of the hands, the vulnerability in a pair of bare feet. The recognition that you can always start again.

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