Chicago, 1920: Gangster Sam Dunleavy has just returned to town, and is visited by Al, a former childhood friend who is now a police officer. Al knows that Sam's girlfriend has just dropped him, and he warns Sam not to try anything violent. But Sam does plan to kill his ex-girlfriend, and he knows he needs an alibi. He sees his friend Barney, who promises to give him a perfect alibi for $2500. They work out the details, and Sam returns to Barney's place later to put the plan into action. But Al also shows up, so Sam knows that the plan must work perfectly.

Petty thief Harold 'Stretch' Sears has served several prison sentences, and is again out on parole. He is given a job as a department store 'Santa Claus', but his cynical nature makes the job difficult. Miss Webster, who arranged the job for him, keeps trying to encourage Sears, but only succeeds in irritating him. As Sears does his best to get through the holiday season, he notices a bad-tempered boy who keeps coming to the store, arguing with him that there is no Santa Claus, and stealing small items from the store. Fearing for the boy's future, Sears feels an odd impulse to do something for the boy

Melvin Hoover, a budding photographer for Look magazine, accidentally bumps into a young actress named Judy LeRoy in the park. They start to talk, and Melvin soon offers to do a photo spread of her. His boss, however, has no intention of using the photos. Melvin wants to marry Judy, but her father would rather she marry dull and dependable Harry Black. As a last resort, Melvin promises to get Judy's photo on the cover of the next issue of Look, a task easier said than done.