4. Ronnie Woo Woo
Roots For: Cubs, cinnamon lozenges
Every staple tourist attraction has its collection of psychopaths leveraging their insanity for tips. Chicago's less recognizable but equally irritating answer to Times Square's Naked Cowboy is Ronnie Woo Woo.
Woo Woo (possibly a phony last name) basically chokes on his own hiccups until you take a picture with him. He echoes the phrase "Go, woo! Cubs, woo!" for literally hours, or until you pay him to stop. It's a business model the borders on extortion. If you've ever had the misfortune of sharing a Red Line car with him, you know what it feels like to have a chemical fire inside of your brain.