Take the Money and Run

One of Allen's first movies, back when he was one of the prime innovators of comedy in film. He's known for creating a lot of jokes and gags that have been recycled endlessly by less creative writers, and Take the Money and Run is the first real Mockumentary. A lot of the movie plays pretty much like a normal movie, but the narration and interviews with people who knew the main character are what make it different. Allen wrote and directed, but Ralph Rosenblum's editing appears to have been very vital to the movie's success. He changed the editing and tightened up the whole thing, making it into a lean comedy gem.

Virgil is a man who appears kind-hearted but is really a career criminal, although he's not great at what he does. There's a lot of great humor about botched heists, failed escape attempts and how a relationship holds up under the strain of breaking the law for a living. The central conceit that it's supposed to be a documentary doesn't really make sense, because most of this stuff would never be filmed in real life, unlike the more mundane subject matter of This is Spinal Tap or The Office. If you just ignore this problem though, you can find a very smart and funny movie. It rewards viewers who remember details and can spot some cultural references (there was an entire bit about an old Game Show I wouldn't have gotten as well without some help). The runtime is pretty quick, and they never spend too much time on one subject. This is where Woody Allen got his start as a "triple-threat", and it's a good movie indeed.