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Big city gambler Nathan Detroit is in desperate need of money to run his game of craps, when he has the idea to bet big gambling guru Sky Masterson. The bet is if Sky can take missionary Sarah Brown on his trip to Havana, Cuba with him, Nathan must pay $1,000 to Sky. If Sky fails, he will pay Nathan $1,000. Will Sky win over the heart of a girl who wants nothing to do with him or will romance blossom between these two opposites?
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