For Fans of Woody Allen

Annie Hall is the correct entry point because it is the film where Allen figured out what he was actually doing. It is formally daring in a way that still lands (the split-screen therapy scene, the direct address to camera) but it is also genuinely funny and genuinely sad in proportions that feel human rather than calculated. Manhattan is more beautiful and more self-regarding. Start with the one that argues with itself.

The comedies are what people remember but Crimes and Misdemeanors is where Allen pressed hardest against something real. It is a film about whether guilt is intrinsic or just a social habit, and it refuses to answer comfortingly. The parallel stories (one farcical, one genuinely grim) eventually converge at a dinner party conversation that is among the bleakest endings in American cinema. It sits in the mind for days.

Allen's fans tend to skip Stardust Memories because it feels like he is complaining about them. He is, a little. But it is also his most Fellini-inflected film, his most formally ambitious, and the one where his obsession with time and regret is most nakedly stated. The audience discomfort is part of the point. It is better than its reputation.

To understand what Allen built and who internalized it, watch Stillman's first three films. The characters are younger, the setting shifts from the Jewish intellectual milieu of the Upper West Side to WASP decline, but the commitment to people who define themselves through ideas and talk themselves into disaster is continuous. Metropolitan in particular has the quality of a film that knows exactly who it is.