Gerry is a talented but down-on-his-luck gambler whose fortunes begin to change when he meets Curtis, a younger, highly charismatic poker player. The two strike up an immediate friendship and Gerry quickly persuades his new friend to accompany him on a road trip to a legendary high stakes poker game in New Orleans. As they make their way down the Mississippi River, Gerry and Curtis manage to find themselves in just about every bar, racetrack, casino, and pool hall they can find, experiencing both incredible highs and dispiriting lows, but ultimately forging a deep and genuine bond that will stay with them long after their adventure is over.
Carefree single guy Charlie Waters rooms with two lovely prostitutes, Barbara Miller and Susan Peters, and lives to gamble. Along with his glum betting buddy, Bill Denny, Charlie sets out on a gambling streak in search of the ever-elusive big payday. While Charlie and Bill have some lucky moments, they also have to contend with serious setbacks that threaten to derail their hedonistic betting binge.
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.
It is 1957. J.C. Cullen is a young man from a small town, with a talent for winning at craps, who leaves for the big city to work as a professional gambler. While there, he breaks the bank at a private craps game at the Gem Club, owned by George Cole, and falls in love with two women, one of them Cole's wife.
When illegal casino owner Charley Kyng develops heart disease, he is advised by a doctor to spend more time with his family. However, he finds it difficult to keep his work separate from his life at home. His son, Paul, feels ashamed of Charley's career and gets into a fight at his prom because of it. Meanwhile, Charley's brother-in-law, Robbin, who works at the casino, begins fixing games due to his extreme gambling debts.
When Joan Boothe accompanies husband-reporter David to Las Vegas, she begins gambling to pass the time while he is doing a story. Encouraged by the casino manager, she gets hooked on gambling, to the point where she "borrows" David's expense money to pursue her addiction. This finally breaks up their marriage, but David continues trying to help her.
Top gaming instructor David Wilhite shows you how to play to win at craps!
Buddy Harris and Frank Radcliffe crack some jokes, play craps, and sing a song.