Guys and Dolls is based on two short stories by Damon Runyon. These tales were set in the gangland subculture of 1950s New York (particularly Manhattan) and followed the lives of several larger than life characters. It is one of the few stage musicals that can genuinely be said to have four leading performers with virtually equal stage time being given to Sky, Nathan, Sarah and Miss Adelaide.

Nathan Detroit is a hustler. He organises illegal gambling in the form of a floating crap game(to avoid detection by the cops the venue moves). He does not gamble himself, he is a hustler not a mug, but rather takes his cut from each pot. He is trying to organise a game as the show opens but cannot find a venue as the heat is on from Lt Brannigan an Irish flatfoot out to clean up the neigbourhood. Assisted by his two sidekicks Nicely Nicely and Benny, he finds a spot but he needs a $1000 deposit which he doesn't have. On top of this Miss Adelaide, his long suffering fiancee, is developing psychological illnesses as a result of Nathan continually dodging her perfectly reasonable demand that her marry her right away.

He decides to try to raise the cash by making a surefire $1000 bet with someone, but there is only one person with that kind of money, Sky Masterson, king of the gamblers, who simply cannot resist a crazy bet. The only problem is Sky never loses. Nathan decides to bet Sky he cannot take a specific girl with him to dinner in Havana. Sky is a smooth operator hasn't found a woman yet able to resist his charms so he glibly accepts. Nathan is delighted and names Sergeant Sarah Brown of the "Save a Soul" Mission - a preacher.

Sky is dismayed, but the bet has been taken and Sky never loses..............

Nathan must hope he does because the local Mafia are entertaining a very important guest from Chicago who wants to shoot crap and does not like to be disappointed.......