How Colbert crushed on Canada — from roasting Canadian bacon to making Windsor the butt of the joke

If his late night bits are any indication, Stephen Colbert's track record suggests he might just be obsessed with us — meaning Canada — in an endearing way.

He's spent decades on both CBS's Late Show with Stephen Colbert and Comedy Central's The Colbert Report treating the country like a middle-school crush of sorts, one that he secretly admires, but takes every opportunity to publicly roast. You know, to show his affection.

Canadian currency, Canadian politics and Canadian culture have all become fodder for the long-running joke that's soon coming to an end, after the host told an audience last July that "next year will be our last season."

At the time, Paramount and CBS executives said the cancellation was "purely a financial decision against a challenging backdrop in late night."

But the announcement raised eyebrows as it came two days after Colbert spoke out against Paramount Global, the parent company of CBS, settling a lawsuit with U.S. President Donald Trump over a 60 Minutes story.

Well, it's next year and the show's final episode is set to air on Thursday, May 21. Ahead of Colbert's CBS sign off, we've compiled some of his most memorable Canadian moments (and jabs).

In a 2014 blog article, Ancestry.ca revealed that it had discovered what it called "the roots of Colbert’s passion for hockey."

Researchers at the company discovered that Colbert's great-great-grandfather, James Quinn, who was born in Ireland in 1830, eventually built a life for himself in Frontenac County near Kingston, Ont.

The company also noted that his great-great-grandmother, Mary Skelton, was also born in Ireland and at some point moved to Canada, where she lived out her last days.

In 2016, when a bill to change Canada's national anthem was passed in Parliament, or what he called "the law igloo," Colbert naturally suggested more edits.

"Please rise and place your hand over your beaver," he told his audience before his rendition was performed by a man dressed in an RCMP uniform.

Lyrics included lines like "Oh Canada, the country we hold dear. All the sexy Ryans, also come from here," in reference to Canadian stars Ryan Gosling and Ryan Reynolds.

Back in 2019, Colbert met with a Toronto-based Canadian immigration lawyer and jokingly took a Canadian citizenship test. When asked to name the three branches of government, he answered "The NHL, Tim Hortons and Alan Thicke."

And when asked for the three responsibilities of citizenship, he included answers like "adding unnecessary U's to words like flavour and colour," and the ability "to sing at least one Gordon Lightfoot song at karaoke."

When Trump announced a tariff on Canadian softwood lumber in 2017, Colbert referred to then Minister of Natural Resources Jim Carr's response — that he "disagrees strongly" — as a Canadian way of saying "F--k you."

Mocking Canada's supposed politeness was a bit he'd often return to.

Over the years, the late night host occasionally interviewed politicians, and in 2024, it was Canada's turn. When former Prime Minister Justin Trudeau sat down, Colbert thanked him for making the time before prompting him with "I hear really good things about Canada, sell me."

Trudeau went on to discuss the idea of a Canadian mosaic vs. the American melting pot and, at Colbert's urging, Canadian bacon.

"What you call Canadian bacon, we call back bacon. Real bacon is in long strips," Trudeau said.

"Thank you," Colbert replied. "I accept your apology."

Trudeau made a more recent appearance, this time garnering a mention after making his relationship with pop star Katy Perry Instagram official. Colbert suggested that in order to make it even, a former U.S. politician would have to steal the heart of a Canadian music star.

"Hillary Clinton, you know what to do!" he said as an image of Drake popped up next to a photo of the former secretary of state.

Tons of Canadian stars also took to Colbert's late night couch over the years, but he said he was starstuck by Schitt's Creek and SCTV co-stars the late Catherine O'Hara and Eugene Levy, calling them "two of his deepest and sincere comedy heroes."

He also burst into song with crooner Michael Bublé, singing a rendition of the popular Canadian sea shanty Barrett's Privateers, and asked Sandra Oh if Canadians are actually really nice, or just "passive-agressive" as he said people from the southern states are.

Windsor, Ont., became the butt of a harsh joke about geothermal power on The Colbert Report in 2012. It all began when the host referred to the border city in his book, America Again: Rebecoming the Greatness We Never Weren't.

"Before we can harness Geothermal power, we have to take the planet's temperature with a geothermometer," he wrote. "And I have no idea where the Earth's rectum is." A footnote at the bottom of the page suggested that was "Windsor, Canada."

Eddie Francis, Windsor's mayor at the time, joked that there were many Windsors in Canada, and Colbert could have been referring to Windsors in Quebec, Nova Scotia or Newfoundland, adding, "I don't even think he's been through the city."

Colbert didn't back down and even used CBC's reporting in a later segment, joking about a poll at the bottom of a CBC News article that asked "Is Stephen Colbert's description of Windsor as the Earth's rectum good or bad for the city?"

WATCH | Colbert vs. Windsor Ont.:

American comedian Stephen Colbert stood by his declaration of Windsor, Ont., as the rectum of the earth, and also took aim at the CBC.