Romantic gangster musical starring Frank Sinatra and Marlon Brando. When Nathan Detroit (Sinatra), a New York gambler, decides to set up a craps game he realises that all that stands in his way is the $1000 he needs to rent the space. As he tries to obtain the money he meets up with old friend Sky Masterson (Brando), a big-time gambler willing to bet on just about anything. Nathan bets Sky $1000 to take a woman of Nathan's choosing to dinner in Cuba. Thinking he has won an easy bet Nathan rests up; he failed to imagine however that Sky and straight-talking, gambling-opposing Sarah Brown (Jean Simmons) would actually hit it off.