Here, the visual is pure dread, but the subject matter is a mixed bag of precision and vagueness, comedy and darkness. Allen plays Kleinman, a passive-aggressive bookkeeper, who is recruited in the middle of the night by a vigilante mob (including David Ogden Stiers and James Rebhorn) to roam the streets looking for a serial strangler. Being a professional coward, and only dealing well with facts and figures in black-and-white, Kleinman is ill-suited for the activity and begs off, inviting suspicion from the group. When there is speculation that maybe he won't do his duty as a citizen because he might be the strangler, Kleinman caves.
On his dark journey through the city streets (the largest set ever built in New York's Kaufman-Astoria Studios, making this Allen's most expensive film), he runs across an all-star cavalcade of slothful potential victims: a philosophy student (John Cusack) with a weakness for prostitutes (among them Lily Tomlin and Jodie Foster, madamed by Kathy Bates), a circus love-triangle tangentially related (with John Malkovich, Mia Farrow and Madonna) and the town coroner (Donald Pleasence), who has a purely scientific interest in the killer.*
Kleinman soon realizes that life simply doesn't add up, that a little slippage occurs, especially when it comes to illusion and reality (in the form of a very handy and practical magician named Armstead, played by Kenneth Mars). The film struggles with the dichotomy throughout, as highly contrasted as the black and white photography, never truly meshing, and finally ends, as many of Allen's weaker films—and one of Allen's strongest ones (Hannah and Her Sisters)—do, with a Deus ex Machina** that buttons everything up inexplicably, leaving no questions but a lot of raised eyebrows.
Which is fine for the purposes of the film, but it's hardly what you'd find in an example of German Expressionism, where the punishment fits the crime...and where things really are in black and white.
* Yes, the film is top-heavy with fine actors (and Madonna), but if you look in the darkened nooks and crannies of the film you'll also find Fred Gwynne, William H. Macy, John C. Reilly, Josef Sommer, Wallace Shawn, Kate Nelligan, Kurtwood Smith and Philip Bosco. Was this film cast or filmed at a SAG convention?
** Here's a question: It's a Woody Allen film; Can there be a Deus Ex Machina if there's no Deus?