An American slacker makes enemies out of the two toughest mafia bosses in Bologna after getting cut off by his wealthy parents, and fleeing to Italy. Charlie Edwards (Bobby Kennedy III) has just graduated from college when his parents hand him a $5000 check, and tell him to finally start acting like an adult. Naturally, the first thing Charlie does is book a flight to Italy, and prepares to party like a true European. But the moment Charlie steps off the plane, he's robbed blind by some tough characters. Fortunately for the wayward American, the self-dubbed King of Bologna is there to lend a helping hand. If any Italian can match Charlie's appetite for mayhem, it's Lele (Lele Gabellone). Upon moving in with Lele and his peculiar roommates -- crusty gutter punk Badoo (Gianlucca Bazzoli) and hooker-happy horn-dog Il Pisa (Giuseppe Sanfelice) -- Charlie picks right up where he left off back in the states, living each day like it was his last. Shortly after charming lovely local Valentina (Alessandra Mastronardi) and pretty American Jessica (Eva Amurri), however, the swaggering American finds that Italy isn't all fun in games after incurring the wrath of Don Farina (Ernesto Mahieux) and Don Fercanne (Giancarlo Giannini), two short-tempered crime-bosses with precious little patience for Charlie's particular brand of tomfoolery.