Buddy Evans manages events at Madison Square Garden in New York City. He is a confirmed bachelor who lives with his housekeeper Celia. After coming into contact with several children, Buddy decides that he is ready to be a father. Buddy decides to hire a surrogate mother in the hope of having a son.
Joe Gideon is at the top of the heap, one of the most successful directors and choreographers in musical theater. But he can feel his world slowly collapsing around him - his obsession with work has almost destroyed his personal life, and only his bottles of pills keep him going.
Famous singer Fanny Brice has divorced her first husband Nicky Arnstein. During the Great Depression she has trouble finding work as an artist, but meets Billy Rose, a newcomer who writes lyrics and owns a nightclub.
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.
Joe Boyd, an aging Washington Senators fan, would sell his soul for the Senators to beat the New York Yankees and win the pennant. Enter Mr. Applegate, who offers to turn Boyd into Joe Hardy, a powerful young baseball player, in exchange for his soul. When Boyd agrees, he becomes Hardy and leads the Senators on a winning streak. When he starts to miss his wife, though, and questions the deal, Applegate sends temptress Lola into the mix.
Harvey Middleman (Eugene Troobnick), a New York fireman, lives a very ordinary life with his wife (Arlene Golonka) and children. After he rescues a beautiful girl (Patricia Harty) from a fire, he fancies himself to be in love with her, leaving his wife and seeking help, in the process, from a nutty Psychiatrist (Hermione Gingold).