Virgil Starkwell’s (Woody Allen) story is told in documentary style, using fake stock footage and ‘interviews’ with people who knew him. He begins a life of crime at a young age. As a child, Virgil is a frequent target of bullies, who snatch his glasses and stomp on them on the floor. As an adult, Virgil is inept and unlucky, and both police and judges ridicule him by stomping on Virgil’s glasses.
Virgil falls in love with a young lady, Louise (Janet Margolin), a laundry worker, they marry and later have a baby.
Virgil attempts to rob a bank, but is arrested when he is embroiled in an argument about the handwriting on a demand note he hands to a cashier. He is sent to prison, but attempts an escape using a bar of soap carved to resemble a gun. Unfortunately for him, it is raining outside and his gun dissolves. He does escape, but by accident. Joining a mass breakout plan, Virgil is the only inmate not warned that the scheme had been called off.
Outside but unemployed, Virgil finds no way to support himself and his family. Eventually, he is rearrested and sent to a chain gang, where he is undernourished (the single meal of the day is a bowl of steam) and brutally punished (consigned to a steam box with an insurance salesman).
Virgil again escapes but is eventually captured when attempting to rob a former friend who reveals he is now a cop. He is sentenced to 800 years, but remains upbeat knowing that “with good behavior, I can get that cut in half”. In the last scene, he is shown carving a bar of soap and asking the interviewer if it is raining outside.