In 1934, Chicago sheet-music salesman Arthur Parker is having a hard time, both in his business and at home with his wife Joan. His business and marriage are failing, and Joan refuses to give him the money she inherited from her father to start his own business.
Arthur’s dream is to live in a world that is like the songs he tries to sell. He is refused a bank loan, although he fantasizes that he gets it. In his travels, Arthur meets schoolteacher Eileen and falls in love with her instantly. They embark on a short affair, but Arthur leaves her and returns to Joan, who is desperate to keep him and agrees to give him the money he wanted. Arthur denies having an affair, though Joan is sure he is lying.
Eileen gets pregnant by Arthur and is fired. With nowhere to go, she takes up with stylish pimp Tom. Eileen is attracted to Tom’s “badness”, and he arranges for her to have an abortion.
When Arthur meets Eileen again, she is now a prostitute calling herself “Lulu”. They resume their romance, and Eileen leaves Tom and her sordid life. Impulsively, Arthur convinces her to run away with him. Having failed to sell his business, Arthur and Eileen break into the store one night and trash it, smashing its phonograph records (except for “Pennies from Heaven”). To supplement their income, Eileen keeps prostituting in spite of Arthur’s objections.
A blind girl whom Arthur knew superficially is raped and murdered by an accordion-playing hobo to whom Arthur had given a ride earlier in the film. The police’s suspicions are confirmed by Joan, who reveals to them Arthur’s sexual predilections to get back at him for cheating on her. The police find Arthur trying to leave town with Eileen, and arrest him for murder; he is soon convicted and sentenced to death. At the gallows, he recites the lyrics from the song “Pennies from Heaven”. In one final fantasy, Arthur and Eileen are reunited, with Arthur saying, “We couldn’t have gone through all that without a happy ending. Songs ain’t like that, are they?”