Sullivan's Travels (The Criterion Collection)

This masterpiece by Preston Sturges is perhaps the finest movie-about-a-movie ever made. Hollywood director Joel McCrea, tired of churning out lightweight comedies, 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, he hits the road as a hobo. He finds the lovely Veronica Lake-and more trouble than he ever dreamed of.