Sullivan's Travels (1941)

The titular pilgrim is John L. Sullivan (Joel McCrea), an Ivy League grad who's enjoyed a meteoric rise as the director behind escapist movies like Ants in Your Pants of 1938, but is now determined to raise his sights toward more exalted, serious-minded cinematic art. His proposed breakthrough, portentously titled O Brother, Where Art Thou?, elicits a studio response closer to "Oh, brother," given the director's utter lack of first-hand experience on the wrong side of the tracks.

Instead of capitulating, Sullivan sets off disguised as a tramp, ready to meet life's crueler lessons face-to-face--albeit followed at a discreet distance by a motor home filled with studio handlers and reporters. His ludicrous odyssey may give the boy director no real insight, but it gives Sturges the chance to inject some reliably fine gags and a romantic subplot featuring the luminous Veronica Lake. It's at this juncture that Sturges the writer's darker objective throws a jolting shift in tone. Suffice it to say that just when a comic, upbeat denouement seems imminent, Sullivan travels instead from the sunlit California of the comedy's early reels toward a darker, relentlessly downbeat world influenced more by the social realism of the movies the hero desperately wants to make. By the final reel, Sturges has flirted with real tragedy, turning his conclusion into a meditation on his own seemingly carefree, dizzily comic art. --Sam Sutherland