California Split (1974)

Director: Robert Altman
Cast: Ann Prentiss, Barbara London, Bert Remsen, Edward Walsh, Elliott Gould, George Segal, Gwen Welles, Joseph Walsh

Synopsis:

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.