Gambler Nathan Detroit has few options for the location of his big craps game. Needing $1,000 to pay a garage owner to host the game, Nathan bets Sky Masterson that Sky cannot get virtuous Sarah Brown out on a date. Despite some resistance, Sky negotiates a date with her in exchange for bringing people into her mission. Meanwhile, Nathan's longtime fiancée, Adelaide, wants him to go legit and marry her.

After aging criminal Roy Earle is released from prison he decides to pull one last heist before retiring — by robbing a resort hotel.

In 1941 Hawaii, a private is cruelly punished for not boxing on his unit's team, while his captain's wife and second in command are falling in love.