Bent on becoming a successful millionaire, ambitious ex-military man Brian (Tom Cruise) serves drinks at a New York City tavern and studies for his degree while waiting for his big break with veteran bartender and cynical mentor Doug.
But all good things must come to an end as Brian tries to raise money in Jamaica to open his dream bar, a chance encounter with beautiful young waitress Jordan (Elizabeth Shue) leads to a whirlwind romance and heartbreak.
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