Ocean's Eleven (1960)

The famous "Rat Pack" is never hipper or funnier than in this, the ultimate Las Vegas movie -- quoted, copied and paid homage to in every movie since that's set in the glamourous desert oasis. Frank Sinatra, Dean Martin, Sammy Davis, Jr., and Peter Lawford star as ex-paratroopers who band together to rob five casinos simultaneously. The caper goes off without a hitch but when one dies of a heart attack, the police seal off the city and the boys must think of a way to get out the loot. Co-starring Angie Dickinson ("Police Woman," "Dressed to Kill").