Sullivan's Travels (1941) (b/w, Criterion Collection)

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Tired of churning out lightweight comedies, Hollywood director John L. Sullivan (The Palm Beach Story's Joel McCrea) decides to make O Brother, Where Art Thou? a serious, socially responsible film about human suffering. After his producers point out that he knows nothing of hardship, Sullivan hits the road disguised as a hobo. En route to enlightenment, he meets a lovely but no-nonsense young woman (I Married a Witch's Veronica Lake) and more trouble than he ever dreamed of. This comic masterpiece by Preston Sturges (The Lady Eve) is among the finest Hollywood satires and a high-water mark in the career of one of the industry's most revered funnymen.