Louisa (Shirley MacLaine) is a widow valued at $200 million dollars. However, she's certain that her fortune is cursed and wants to donate all her money to the IRS. The IRS thinks she’s crazy and sends her to a psychiatrist. As she explains her depressing tale to her psychiatrist, Dr. Stephanson (Robert Cummings), it seems that when Louisa was young she had the option of marrying rich Leonard Crawley (Dean Martin) or poor Edgar Hopper (Dick Van Dyke). She chose Edgar, but soon he became fixated with providing a fine house and wealth for her. Edgar worked so hard but died prematurely because of his drive to be rich. Hopeless, Louisa flies to Paris, where she engages a romance with artist Larry Flint (Paul Newman). Larry invents a machine that creates paintings based on sounds. He becomes rich and famous, but dies. Louisa returns to America, hoping to find the right guy that won’t die, and marries Rod (Robert Mitchum), a business tycoon who was born wealthy. Rod decides to live in a farm and take life slow and easy, but also dies in a freak accident with a bull. Sad and miserable, Louisa ends up in a sleazy nightspot and falls in love with mediocre entertainer Jerry (Gene Kelly). They marry, and a newly wealthy Jerry develops a relaxed, happy-go-lucky quality to his act that makes him a big star, which leads to his death from being trampled by a mob of his biggest fans.