Stephen Colbert’s Funniest Mentions of Sheboygan on 'The Late Show' | Best Moments (2026)

Sheboygan, a small city in Wisconsin, has unexpectedly become a frequent topic of discussion on Stephen Colbert's 'The Late Show'. The city's name has been invoked in various jokes and references, often with a humorous twist. From 'funny name towns' to political commentary, Sheboygan's unexpected fame on late-night television has sparked curiosity and even a visit from the city's mayor.

One of the most memorable moments came when Colbert joked about the arrest of Luigi Mangione, a character in the movie 'Home Alone'. He playfully associated Sheboygan with the idea of a 'funny name town', suggesting that the police would find anyone, no matter the location, quickly. This light-hearted approach to the city's name has become a recurring theme, with Colbert using it to create a sense of familiarity and humor.

In another instance, Colbert made a playful comparison between Sheboygan and Milwaukee, both cities in Wisconsin. He mocked President Donald Trump's comment about Milwaukee being a 'horrible city' by drawing a parallel to Sheboygan's seemingly unexciting reputation. Colbert's witty remarks about Sheboygan's lack of sharks and its proximity to Milwaukee, which he affectionately calls 'the eternal city', have become a running gag, leaving audiences both amused and intrigued.

The city's name has also been used to mock political figures, such as former President Joe Biden. Colbert's impersonation of Biden, where he jokes about Sheboygan's proximity to Scranton and Wilmington, adds a layer of humor to the political commentary. These references not only showcase Colbert's comedic talent but also highlight the city's unique place in the public consciousness.

What makes these references particularly fascinating is the unexpected fame of a small city like Sheboygan. It raises questions about the power of media and the impact it can have on local communities. Additionally, it demonstrates how a simple name or a playful reference can become a source of pride and identity for a city and its residents.

As 'The Late Show' concludes its 11th season, it's interesting to reflect on the impact of these references. They have not only entertained audiences but also sparked conversations about the city's unique characteristics and its place in the broader cultural landscape. Perhaps, in the future, Sheboygan will continue to be a source of unexpected humor and a reminder of the power of media to shape our perceptions.

Stephen Colbert’s Funniest Mentions of Sheboygan on 'The Late Show' | Best Moments (2026)
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