John Sullivan has built a successful career directing comedies, but something about his job is unfulfilling. He wants to document the pain and despair of real people living in the shadow of the Great Depression—not filming another farce. To research his great American tragedy, O Brother, Where Art Thou? (a title the Coen brothers appropriated for another film on this list), he embeds himself among America’s underclass, becoming a homeless man and riding the rails. His misadventures eventually land him on a chain gang where a transcendent encounter with a cartoon shows him the liberating power of laughter.
—Tyler J. Petty