Among his extensive (and mostly impressive) oeuvre, Woody Allen has two undeniable masterpieces. The first is Annie Hall. The second is Manhattan, the tale of a writer having a bit of a mid-life crisis.
Allen plays Isaac, a divorced New York comedy writer and would-be novelist who is dating a high-school student (Hemingway) and yet finds himself falling for his best friend's mistress, the journalist Mary (Keaton).
Manhattan is a film full of wonderful moments, wonderful lines and wonderful gags. It's one of the few films that Allen got totally right – the tone, the look, the casting, the script, the setting – everything is just perfect. Is it a romantic comedy? It's certainly a very funny film, and sure it's romantic, but is it a film about love? I think I would have to agree with the great, late Roger Ebert, who said that it's a film that is more about loss than about love. It's certainly one of Allen's best performances. His Isaac is a deeply flawed man: insecure, immature (why else would a man of 42 be dating a 17-year-old?), unsure of his place in the world and unsure of his future.
With the beautiful city of New York playing a major role, along with a superb Gershwin score, Manhattan is one of the greatest films of the 20th century – a true masterpiece of cinema on every level.