America's Most Devoted Canada Hater (Who Clearly Loves Us)
For decades, Stephen Colbert has had a complicated relationship with Canada — the kind that feels a lot like a middle-school crush you'd never admit to. Equal parts admiration and relentless ribbing, his Canadian references over the years have become a beloved tradition for viewers on both sides of the border.
As Colbert signs off from The Late Show with Stephen Colbert, CBC has rounded up some of his most memorable Canadian moments — and they're a reminder of just how much real estate this country has occupied in the comedian's mind.
From Canadian Bacon to Windsor Burns
No Canadian sacred cow was safe from Colbert's jokes. Canadian bacon — that uniquely North American point of culinary confusion — took its share of roasting over the years. But perhaps no Canadian city bore the brunt of Colbert's affection-disguised-as-mockery quite like Windsor, Ontario, which became something of a recurring punchline in his arsenal.
It's the kind of gentle ribbing that Canadians have come to expect from their American neighbours: simultaneously dismissive and weirdly flattering. Because if Colbert is talking about Windsor, he's thinking about Windsor — and that counts for something.
A Love Language Built on Jabs
What made Colbert's Canada bits work was that they never felt mean-spirited. There's a difference between punching down and teasing a sibling, and Colbert always seemed to understand which side of that line he was on. Canada, in his telling, was always the slightly-too-earnest neighbour with great healthcare and suspiciously polite citizens.
That framing — Canada as likeable underdog, beloved but easy to tease — is something Canadians have always quietly appreciated. Better to be noticed than ignored, after all.
Why It Mattered
For Canadians who've long watched American late-night television hoping for even a passing mention of home, Colbert's repeated returns to Canadian material felt like a small but genuine validation. His willingness to engage — even through mockery — acknowledged that Canada is more than just a backdrop for America's stories.
At a time when Canada-U.S. relations have carried more weight than usual, the long archive of Colbert's Canadian moments takes on a different tone. The jokes still land, but there's something almost wistful about them now — a reminder of the easy, affectionate dynamic that has historically defined the two countries' relationship.
The End of an Era
Colbert's Late Show run has been one of the defining chapters in American late-night television. His willingness to go after political absurdity with both wit and genuine feeling set him apart — and his Canadian material, however niche, was always part of that broader portrait of a comedian who paid attention to the world around him.
As he takes his final bow, Canada can at least claim this: we were part of the bit. And in Colbert's world, that was always a compliment in disguise.
Source: CBC Top Stories — Stephen Colbert's most memorable Canadian moments
