Carefree single guy Charlie Waters (Elliott Gould) rooms with two lovely prostitutes, Barbara Miller (Ann Prentiss) and Susan Peters (Gwen Welles), and lives to gamble. Along with his glum betting buddy, Bill Denny (George Segal), 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.