5. THE TONIGHT SHOW WITH CONAN O'BRIEN (2009)
The very first Conan O'Brien show after he replaced Jay Leno on June 1, 2009. He discovers that he needs to be in Los Angles instead of New York. Unable to get a cab, he sprints across the country a la Forrest Gump. To the tune of Cheap Trick's "Surrender" he runs and goes through Chicago and across the field at Wrigley with security guards in hot pursuit.
Watch the video on You Tube. Hilarious.
6. UNDERCOVER BOSS (2010)
New Cubs owner Todd Ricketts grew a beard and wore fake glasses with the name Mark Dawson (from Cubs players Mark Grace and Andre Dawson) and applied for jobs in and around the ballpark. Some of the jobs he did was cleaning restrooms and trying to organize a remote parking lot. He wasn't very good at either job.
But, he really failed at selling hot dogs. His solution was to buy them all himself and toss them in the garbage. But, his supervisor caught him.
--CootRicketts
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