Nathan Detroit, a gambler in 1920's New York City, needs a place to hold his illegal dice game where he will not be caught by the police. He finds a place, but the person who owns it wants one thousand dollars to rent it for the night. Nathan thinks he is out of luck, until he hears that the famous gambler Sky Masterson is in town. He bets Sky one thousand dollars that he cannot get Sarah Brown, a missionary, to go to Havana, Cuba with him. Because Sarah is very religious and moralistic, Nathan thinks she will never agree to go with him.