+3
With probably the most notable filmography in the history of cinema, it is impossible to list only 5 of his films.
I think only 3-4 of them can't be called masterpieces.
I've seen most of his films numerous times (some of them 10-12 times and can't stop do it). Woody is also superb when act in his works. It took me some time to get used to when he stopped acting.
For a man like me who just live with the art in his veins, I can't imagine the life without a new movie by Allen every year and constant re-watch of all titles in his catalog.
Anyway, here are my top 10 listed chronologically:
Take the Money and Run
Annie Hall
Broadway Danny Rose
Hannah and Her Sisters
Radio Days
Husbands and Wives
Deconstructing Harry
Vicky Cristina Barcelona
Whatever Works
You Will Meet a Tall Dark Stranger
---
Damn, can't stop...what a feast...
The Curse of the Jade Scorpion
To Rome With Love
A Rainy Day in New York