When his wife won't let him invest their small savings, a man wishes he could live his life again so that he could make money.
Joe Gimlet (Lee Tracy) and his wife Mary Gimlet (Mae Clarke) sell tobacco products as Franklin Roosevelt becomes President and closes the banks. Wealthy Ted Wright (Otto Kruger) invites them to dinner. Elvina Wright (Peggy Shannon) remembers Joe after 22 years. Joe sees Elvina holding hands secretly with Mr. Holmes (C. Henry Gordon). Ted advises Joe to invest his $4,000 to make much more, but Mary says no. At home Joe keeps pestering her and finally says he will get drunk until she agrees. Joe is hit by a car. In the hospital he is given gas and goes back in time.
Joe wakes up and is glad to see his mother (Clara Bandick). Joe realizes it is twenty years earlier. His mother makes him see a doctor. Joe says he will go for money this time. Joe works in a drug store and suggests they serve food. Elvina comes in with her father Evans (George Barbier), who asks Joe to invest his $400. Joe says no but changes his mind. Joe loves Mary but tells her he must marry Elvina for money. Joe weds Elvina and sees Mary with Ted. Joe gets drunk and does a new dance. He decides to invest in automobiles and says the war will need trucks. Holmes pays attention to Elvina. Joe speaks to soldiers going to war and says he will give them money when they come back. Joe is summoned to see President Wilson. Joe warns him, and Wilson thanks him for his generosity. Joe calls Elvira a two-timer and wants a divorce; but the press informs him he was appointed head of the war industries board. He and Elvina pose for photos. Joe tells her the divorce is off. Joe can't go out with Elvina but learns he was fired.
In 1929 Joe is a banker. Elvina tells Joe to buy stocks from a Holmes' tip; but Joe says he keeps his money in a trust fund. Joe finds Ted working in a cigar store. Joe sees Mary again and asks if she is happy. Joe offers to invest Ted's money, and Mary agrees. Joe takes them out. Elvina tells Holmes she is not putting Joe's money in the trust fund. Joe tells Mary that money does not bring happiness. Stocks crash, and Elvina says she lost their money. Joe says he lost his self-respect and never wants to see her again.
On March 6, 1933 Joe learns that his bank is corrupt and is being investigated. Joe resigns and goes to Mary, asking her to leave with him; but she wants to stay with Ted. Joe hears on radio he is wanted by the police. He flees them but is captured by the police. Joe wakes up in the hospital. His wife Mary visits him with Ted and says Joe can have the $4,000; but Joe says no and that he would not trade places with Ted.
This fantasy helps a man see that wealth does not always produce happiness even when he knows ahead much of what will happen. His hindsight gives the story of twenty years many ironies as he fails to correct some of the mistakes.