What is Woody Allen's darkest movie ever? It's a difficult question to answer, since from the mid 80s to the late 90s, pretty much every one of his movies is rather dark (might have something to do with the demise of a certain relationship).
What is Woody Allen's Jewiest movie ever? That question is even more difficult, since EVERY one of his movies is rather Jewy. Some more than others, sure, but this is Woody, after all.
The answer to both questions might just be "Crimes and Misdemeanors".
The movie is incredibly dark. It deals with — spoiler alert — a murder of a man's mistress and falls into depths of Dostoyevskyan despair.
The movie is incredibly Jewish, and we're not just talking about Martin Landau, who plays the main character. At the heart of the movie is a rabbi, who Landau consults with his dilemma.
So yes, Woody Allen's darkest movie is also his Jewiest movie.