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This summer, John Semley asks the tough questions of our nation: Are we Canadians really a funny people? And, if so, how did we get that way? Each week, for 10 weeks, he will explore a new facet of our history in humour. For the previous instalment, click here.

Like Gretzky, Celine, Bieber and Wolverine, Stephen Leacock was that rarest of Canadian commodities: a real-deal celebrity.

Leacock was Canada's Mark Twain. He counted Groucho Marx, Jack Benny and F. Scott Fitzgerald amongst his public admirers. Charlie Chaplin petitioned him to write a screenplay. His books and articles and punditry were published across the English-speaking world. The New York Times even asked him to write a series of articles about the looming spectre of bolshevism, something a Canadian humourist and career political scientist was, apparently, uniquely qualified to comment on.

Stephen Leacock was also an Imperialist, a staunch opponent of woman's suffrage and non-white immigration into Canada. "Separate the art from the artist!" we tell ourselves, a way of permitting the enjoyment of Chinatown or "Trapped in the Closet" without the image of a child being violated creeping in the backdoor of our compromised consciousness. But Leacock was as much as product of his times as a producer of those social standards, his status as a formidable public intellectual (and pro funnyman) not just reflecting the embarrassing cultural norms of inter-war Canada, but actively shaping them.

Beyond his more historically particular prejudices – which we can ascribe, however lazily, to it being "a different time" – there runs through Leacock's writing a deeper vein of narrow-mindedness. His work, like 1912's classic of our national humour canon, Sunshine Sketches of a Little Town, reveals an unfortunate fundament of the Canadian character: our ambivalence.

The aim of humour, Leacock wrote in 1937's Humour and Humanity, was nothing more than "the kindly contemplation of the incongruities of life." Sunshine Sketches follows this line, indexing the mostly charming eccentricities and modest hypocrisies of the citizenry in the made-up Ontario town of Mariposa (modelled, it is widely believed, on Orillia). Mariposa and its people, we're told, are quirky and odd and funny in their own way – naïve and simple-hearted and so are we, to paraphrase Dostoyevsky's patricidal epic The Brother Karamazov.

Leacock, admittedly, is masterful at exposing the cracks in the human veneer. Problem is: he never bothers to pry open those cracks, revealing the gaping chasms of hypocrisy that so often typify humanity, and the world we're born to putter around in, quirks and all. There's a coddling, conservative sense that people are fine just the way they are. And so life's abiding rhythm rolls on, undisturbed. It's kindly as hell, sure. But it reeks of condescension and of a desire to propagate those same attitudes, to instill in the reader this same standard of ho-hum complacency.

In Sketches, Leacock wants to draft a kind of cognitive map, not only of Mariposa's literal geography – "the barber shop, you will remember, stands across the street from Smith's Hotel" – but our recognition of it. It's one thing to read something that rings of real life, but quite another to prod us into this recognition with a shrewd "you'll remember."

These little ticks – elsewhere: "But everybody knows," "You have noticed already," "I suppose you have often noticed," etc. – lumped together, amount to one of my biggest beefs with Leacock. It feels less like he's revealing the Platonic ideal of small-town Canada, and more like he's manufacturing our recognition of it. It's sly and insidious, like Leacock's one of those alarmist psychotherapists in the eighties who used hypnotism and suggestion to convince kids they were being ritually abused by Satanic cults. Our memories of Mariposa are false memories, implanted by the author.

Later in Sketches, Leacock (or his narrator stand-in, anyway) directly fingers the readers as the lost sons and daughters of Mariposa who have fled the little town, probably for the crueler comforts of some godforsaken metropolis, and need only be reacquainted with the humble charms of rural living, where shaving isn't "the hurried, perfunctory thing that it is in the city." The sneering at hustling-bustling city-folk was further explored in 1914's Arcadian Adventures of the Idle Rich, its peeling away of upper-crust foibles and the hypocrisy of academic dilettantes making it an unlikely best-seller in Bolshevik Russia.

In these writings, Leacock's guilty of the same boring, marrow-level conservatism that perpetuates the urban/rural divide, that rallies Ford Nation and leads to my dad calling me on a Sunday to suggest I write an article about how his small-town Ontario tax dollars are being squandered on some downtown Toronto subway he'll never use. Cities, despite being ports for landing immigrants and lively patchworks of diversity and difference, are somehow un-Canadian. For all his chin-stroking consideration of our national character, Leacock holds no other apparent ambition for Canada beyond its function as a bucolic backcountry for the British Empire.

As to the matter of whether it's funny, well, beyond its wit and oldfangled insights into the peccadilloes of priests and barbers and mining prospectors, it's always fun to see the word "aeroplane" spelled like that.

Next week: We trek from Mariposa to Quebec, just for laughs.