Mr. Deeds Goes to Town (1936)

Fable. A small-town greeting card poet inherits $20 million from an uncle and is promptly circled by lawyers, reporters and hangers-on in New York. Gary Cooper plays Longfellow Deeds as a man whose good sense looks like madness to everyone who wants a piece of him, and Frank Capra won the Best Director Oscar for it. The question it poses is the most generous on the list: Deeds decides to give away free farms to struggling families, and the city tries to have him declared insane for it. Its Great Depression setting makes that plan feel urgent rather than quaint. The 2002 Adam Sandler remake exists; this is the one to watch.