Buster Keaton asks the father of the woman he loves for her hand in marriage, but the father wants to see Keaton make something of himself first. "I'll leave for the city to make good. If I'm not a success, I'll come back and shoot myself," Buster declares, which is a perfectly acceptable arrangement as far as the father is concerned. So Keaton heads off for the big city and tries his hand at a number of different jobs. But his letters to his girl suggest more noble and enterprising careers than those he's actually attempting.

The opening scene, a dream sequence prior to the vaudeville routines which follow, is what makes this film famous. In it Keaton plays everyone in a theatre simultaneously (through multiple exposures). He is the band leader, all its members, the dancers on the stage and everyone in the audience.