At first, Urbania threatens to be another whiny GenX story about failed relationships. Charlie pines for his ex, making rambling, pleading phone calls to answering machines and languishing in his now-too-big bed, his hand lingering on the empty pillow beside him. He roams the rainy downtown streets encountering urban legends come to life everywhere, from the lady who microwaves her poodle to the man who gets a nasty surprise the morning after a one-night stand. Are we meant to see these shit-happens stories as a counterpoint to Charlie's woes, I began to wonder, or a validation of Charlie's unspoken contention that the world truly sucks? Either way, it was hard to feel much sympathy for Charlie's broken heart with this seemingly ordinary agony we've all suffered played out so melodramatically. By the time Charlie endures listening to his randy upstairs neighbors go at it by masturbating in time with them -- he's got no one else to play with, see -- the film veers dangerously close to ludicrous self-indulgence. Charlie was past beginning to annoy me.

But then Charlie's restlessness turns more thoughtfully introspective, and in the process throwing into question all that has come before. His nocturnal wanderings take on an unreality that leaves you wondering just how much of what Charlie does and says and witnesses actually occurs. He sees a beaten-up man in the deserted city streets -- or is the man just a horrifying vision? Does Charlie actually and deliciously insult his upstairs neighbors (William Sage: American Psycho, Boiler Room; and Megan Dodds) when he runs into them, or does he just imagine himself doing so? How true is the story bartender Matt (Josh Hamilton) tells Charlie -- did a beautiful older French woman come into Matt's bar one night , and did she really pay him to do what he did for her?

More dangerous imaginings are at hand, too. A passing glance with a neighborhood stranger days earlier has left Charlie with an urgent desire for another encounter -- as he tells his friend Brett (Alan Cumming: The Flintstones in Viva Rock Vegas, Eyes Wide Shut), this could be the one, the person who'll bring Charlie out of his depression for good. But once Charlie finally contrives a meeting with the attractive stranger, an encounter that initially seems as if it will merely smash Charlie's romantic illusions turns terrifying... or does it?

Though Urbania gets off to that slow and rather inauspicious start, it more than redeems itself by its end. Dan Futterman carries the film single-handedly, keeping Charlie's confusion and heartache utterly real, with a simmering intensity behind his apparently numb calm.

And the urban-legend motif, which I at first feared would prove a contrived folly, pays off as well. Shear and Reitz want us to share in the horror that sometimes infects life in the big city (Charlie has a t-shirt in his closet emblazoned with "Way to Survive") -- urban legends themselves, for all that they are not true, are cautionary tales about misbehavior, trusting (or, paradoxically, mistrusting) strangers, about the awful things that could happen, even if they haven't, in the everyday world. While Charlie's story has the tinge of a FOAF story about it, it is more the counterpoint to urban legends I initially suspected it was, but one with more bite than I first imbued it with. Just as urban legends offer us fantasy warnings about possible danger, Charlie's own flight of horrible fancy ultimately deter him from a much worse fate than he deserves. And like the much lighter Nurse Betty, Urbania offers us fantasy as a way to dodge and deal with the most dreadful kinds of events we ever face.

Never a pleasant film, Urbania will leave you uncomfortable in the best way that films can. Don't miss it.