Dr. Feelgood Bloody Mary
Rockit Bar & Grill (address and info)
Near North Side
This is actually a $32 Bloody Mary, but it makes the list because of the amazing toppings (and bottomings?). If you're up on your Bloody Mary goings-on (exhibit A and exhibit B), you'll know that this 32oz Bloody is garnished with a slider (and also shrimp, bacon, peperoncini, grape tomatoes, blue cheese-stuffed olives, and a pickle spear).