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Chicago Olympic Videos, Chicago Olympic Pictures, and Chicago Olympic Articles
When cousin Bill visits Chicago for the first time, Cook County Social Club greets him with penache.
Americans for Prosperity Cheer Chicago's Failure
The conservative group, Americans for Prosperity, cheers when they hear the news of Chicago's failure to host the 2016 Olympics.
It Could Be Worse...David Letterman
David Letterman was blackmailed for $2 million dollars, but Alex thinks its fake! Featuring Chicago doesn’t get the Olympics, the Pope eats spiders, Kanye a...
Educational video for Scatterbrained, an illness that affects the mind. Winner of the December Vidiocy contest at the world famous I.O. Theater in Chic...
Kumail Nanjiani is leading the latest Chicago invasion of comedians in NYC. He has been featured in Variety's “10 Comics to Watch,” the Hollywood Reporter's ...
ThoseGuysFilms.com - The Need to Win
To get ahead in the business world, you have to want it more than the other guy. *Note: Guest Starring Allison Bills of The Second City and The iO Theaters...
Wrigley Field and iO Are Really Close
Two legendary Chicago institutions, Wrigley Field and comedy theater iO, are located very very close to each other. Ask anyone. I attempt to prove just how c...
IOC's 12 Reasons They Picked Rio Over Chicago (Doug's Dozen #13)
Those bastards! But...like bastards everywhere, they had their reasons...
Fuck You, Winter
This is what happens when you live in Chicago, home of the 9-month winter. Written and performed by The Second City, video by Flashpoint Academy.