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History

Chicago’s 1933 Century of Progress World’s Fair brought futuristic hope during the Great Depression. Held on Northerly Island, it drew nearly 39 million visitors with groundbreaking tech like the Burlington Zephyr, the Sky Ride, corporate pavilions, and even Sally Rand’s famous fan dance.This video explores how the fair transformed Chicago, its lasting impact on the city skyline, and why today’s World’s Fairs can’t compete with a good old state fair.

Trivia

Why does Chicago’s Tribune Tower have fragments from famous landmarks embedded in its walls? Colonel Robert McCormick sent his foreign correspondents around the world in the 1920s to collect pieces of the Great Wall of China, the Parthenon, the Great Pyramid of Giza, the Taj Mahal, and many more — nearly 150 in total. 

In this video, Bob explains the eccentric history behind the collection while Shrog gets unexpectedly (and hilariously) involved. A perfect mix of Chicago trivia and on-location comedy.

Hilarity

In this hilarious retro parody, Chicago Bob brings back the gritty 1959 black-and-white style of the classic TV series The Untouchables with a fully Chicago-fied twist. Reimagined as “The Un-Chicago Bobables,” the video features dramatic narration, shadowy Windy City streets, and a fictional episode titled “The Mayor’s Hot Mess,” starring Chicago Bob as the incorruptible hero and Mayor Brandon Johnson in a chaotic special guest cameo. 

A loving, over-the-top spoof packed with political satire and absurd local humor — perfect for fans of retro TV and Chicago comedy.