Im going to say "love and death" ive seen his films and that one defines his character.

Crimes and Misdemeanours was a good movie that defined Woody Allen, he played a good role in that one.

Bananas. Fielding Mellish (Woody Allen) is a neurotic blue collar man who tries to impress social activist Nancy (Louise Lasser). Trying to get in touch with the San Marcos revolution, he visits attempting to show his concern for the native people. However, nearly killed by the local caudillo, only to be saved by the revolutionaries, he is then indebted to help them. Mellish clumsily learns how to be a revolutionary, and then in an effort to feed the troops goes to a restaurant and in typical New Yorker fashion asks for thousands of deli sandwiches (including one special order), plus wheelbarrows of coleslaw on the side. When the revolution is successful, the Castro-style leader goes mad (declaring at one point that all underwear be worn on the outside), forcing the rebels to place Mellish as their President. When traveling back to the U.S. to obtain financial aid, he reunites with his activist ex-girlfriend and is exposed. In a classic courtroom scene, Mellish tries to defend himself from a series of incriminating witnesses (including J. Edgar Hoover disguised as a black woman). He is eventually sentenced to prison, but his sentence is suspended on the condition that he doesn't move into the judge's neighborhood. Nancy then agrees to marry him. An announcement before the closing credits: Special news bulletin ... the astronauts have landed safely on the Moon and have erected the first all Protestant cafeteria"

I liked "Play it Again Sam" because I am a big Bogey fan. Really like "Bananas" too.

Probably in my opinion Love and Death, Annie Hall, Manhattan, Hannah and Her Sisters, and Deconstructing Harry. Hannah and Her Sisters is my favorite.

Anything Else.

Bananas Take the money and run Sleeper Everything you ever wanted to know about sex (but were afraid to ask) These are the films I believe define him as a comic genius. In my opinion he went downhill starting with Annie Hall, But that's just me.