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Chicago... How about Chicago? Or The Untouchables? Or any other Capone-centered flick. The Blues Brothers. High Fidelity. Hoop Dreams. My Best Friend's Wedding. The Sting. Adventures in Babysitting.
New York... Godfather I and II. The Seven-Year Itch. Barefoot in the Park. An Affair to Remember, and its cheeseball protege, Sleepless in Seattle. Allen, duh, (Annie Hall's the best) but also much of Scorcese. From the Mixed-Up Files of Mrs. Basil E. Frankweiler. Breafast at Tiffany's is my favorite, though.
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