If Stephen Colbert’s late-night comedy over the years is anything to go by, he may have had a soft spot for Canada all along — expressed through the kind of teasing that usually comes with affection.
Across both The Late Show with Stephen Colbert on CBS and The Colbert Report on Comedy Central, Canada often became a recurring punchline. Whether it was the country’s politics, currency, or culture, Colbert repeatedly poked fun at Canadians in a way that felt more playful than hostile — almost like someone roasting a longtime crush.
That running gag is now coming to an end. In July last year, Colbert told his audience that the upcoming season would be the show’s last. Paramount and CBS later explained the cancellation as “purely a financial decision against a challenging backdrop in late night.”
Still, the timing raised questions. The announcement came just two days after Colbert criticized Paramount Global — CBS’s parent company — for settling a lawsuit with U.S. President Donald Trump related to a 60 Minutes segment.
Now, with the final episode scheduled to air on Thursday, May 21, it’s a fitting moment to look back at some of Colbert’s most memorable Canadian jokes, interviews, and moments.
Discovering his Canadian roots
In 2014, Ancestry.ca published a blog post claiming it had uncovered “the roots of Colbert’s passion for hockey.”
According to the research, Colbert’s great-great-grandfather, James Quinn, was born in Ireland in 1830 before eventually settling in Frontenac County near Kingston, Ont. His great-great-grandmother, Mary Skelton, also emigrated from Ireland to Canada, where she later spent the rest of her life.
Colbert rewrites “O Canada”
When Parliament passed a bill in 2016 to update the lyrics of Canada’s national anthem, Colbert couldn’t resist putting his own spin on it. Referring to Parliament as “the law igloo,” he introduced a parody version of the anthem with the line: “Please rise and place your hand over your beaver.”
The performance, delivered by a man dressed as an RCMP officer, included lyrics such as: “Oh Canada, the country we hold dear. All the sexy Ryans, also come from here,” referencing Canadian actors Ryan Gosling and Ryan Reynolds.
The mock citizenship test
In 2019, Colbert teamed up with a Toronto immigration lawyer for a comedic Canadian citizenship test.
Asked to name the three branches of government, he replied: “The NHL, Tim Hortons and Alan Thicke.”
When the conversation turned to the responsibilities of citizenship, Colbert joked that Canadians must know how to add extra “u”s to words like “flavour” and “colour,” and be able “to sing at least one Gordon Lightfoot song at karaoke.”
Poking fun at Canadian politeness
Canada’s reputation for politeness was another favourite target.
After the Trump administration imposed tariffs on Canadian softwood lumber in 2017, then-natural resources minister Jim Carr said Canada “disagrees strongly.” Colbert joked that this was the Canadian equivalent of saying “F–k you.”
Conversations with Canadian politicians
Canadian politicians occasionally appeared on Colbert’s show, including former prime minister Justin Trudeau in 2024. Welcoming him to the program, Colbert joked: “I hear really good things about Canada, sell me.”
The interview touched on Canadian identity, including Trudeau’s explanation of Canada as a cultural mosaic rather than an American-style melting pot. The two also discussed Canadian bacon.
“What you call Canadian bacon, we call back bacon. Real bacon is in long strips,” Trudeau explained.
“Thank you,” Colbert responded. “I accept your apology.”
Trudeau later received another mention after publicly confirming his relationship with singer Katy Perry on Instagram. Colbert joked that to balance things out, an American politician should date a Canadian music icon.
“Hillary Clinton, you know what to do!” he quipped while images of Clinton and Drake appeared onscreen together.
Canadian celebrities on the couch
Over the years, many Canadian entertainers appeared on Colbert’s programs. He once described Schitt’s Creek and SCTV stars Catherine O’Hara and Eugene Levy as “two of his deepest and sincere comedy heroes.”
Singer Michael Bublé joined him for a performance of the Canadian sea shanty Barrett’s Privateers, while actress Sandra Oh was asked whether Canadians are genuinely nice or simply “passive-aggressive,” as Colbert compared them to people from the American South.
The Windsor joke that wouldn’t die
One of Colbert’s harshest Canadian jokes targeted Windsor, Ont. In his 2012 book America Again: Rebecoming the Greatness We Never Weren’t, he wrote:
“Before we can harness Geothermal power, we have to take the planet’s temperature with a geothermometer. And I have no idea where the Earth’s rectum is.”
A footnote added: “Windsor, Canada.”
At the time, Windsor mayor Eddie Francis laughed off the insult, pointing out there were several places named Windsor across Canada — including in Quebec, Nova Scotia, and Newfoundland — and joked that Colbert probably had never even visited the city.
Colbert doubled down later, even referencing CBC News coverage of the controversy. He highlighted an online poll attached to one CBC article asking readers: “Is Stephen Colbert’s description of Windsor as the Earth’s rectum good or bad for the city?”
Harnaik Singh Rathor is the Founder, Publisher, and Editor-in-Chief of StudioX News Canada, Canada's multilingual digital news network serving diaspora communities across 44 languages. With a background in media production, public relations, and multicultural communications, he founded StudioX Film and TV Corporation to bridge the gap between mainstream Canadian media and the country's diverse immigrant communities. He is a member of the Canadian Association of Journalists (CAJ), RTDNA Canada, CPRS Vancouver, Unifor, NEPMCC, and the Canada Freelance Union. He holds CAVCO Personnel Number SINH0106. Based in Surrey, British Columbia. | LinkedIn: https://www.linkedin.com/in/harnaiksinghrathor/ | Muck Rack: https://muckrack.com/harnaiksinghrathor | Email: editor@studioxnews.ca
