Monty isn't the scum of the earth, actually, and it's the avoidance of stereotype and cliché that ultimately makes him more sympathetic than he might otherwise be. Edward Norton (Frida, Death to Smoochy) brings him to life as a morally complicated man just coming to understand what he's led himself into and terrified of what making up for it is going to entail. But the film offers no excuses for Monty, no glorification of or justification for his misdeeds -- Monty doesn't let himself off easy, his friends don't let him off easy, and Lee and screenwriter David Benioff (working from his own novel) don't let him off easy. Monty isn't a hero in any sense, no one to be emulated, obviously, and there's nothing much noble in him, except perhaps that he's finally acknowledging that his life has gone wrong and needs to be fixed. But does fixing it mean facing prison or running away?

On Monty's agenda for the evening are his girlfriend, Naturelle Rivera (Rosario Dawson: Men in Black II, Sidewalks of New York) and his father, James (Brian Cox: Adaptation, The Ring), though Monty's more inclined to avoid them, their disappointment in him, and his own disappointment in himself for having to abandon them, one way or another. Better to reconnect with old pals, friends from childhood, who fall in various places along the spectrum of risk-taking that Monty's right on the edge of. Jacob Elinsky is a nervous schoolteacher both horrified and intrigued by his attraction to a student (Anna Paquin: Finding Forrester, X-Men); Philip Seymour Hoffman (Punch-Drunk Love, Almost Famous) gives Jacob his usual redoubtable all, making Jacob's dilemma as compelling as Monty's. Francis Slaughtery, hotshot stockbroker and ladies' man, is the flip side of Monty, where Monty might have gone if he'd stayed on the right side of the law; Barry Pepper (Knockaround Guys, Battlefield Earth) is 25th Hour's biggest and best surprise -- I've always suspected he was a terrific actor who just hadn't yet had the chance to show it, and here, as the stand-in for the audience's sympathy for and anger with Monty, he's powerfully moving. We've become Francis by the end of the film, as it builds to a painful crescendo of all that Monty is not going to have, and all because of his own stupidity. We love him like a brother, but the stupid dumb fuck deserves what he's getting, and we hate ourselves for liking Monty so much, hate him for what he's done to us and to himself. Pepper encapsulates that entire rage of conflicting emotions in one heart-rending scene toward the end, in which Monty asks him for one last favor.

Only a New York filmmaker could have been the first one to approach September 11 head-on like Lee does here, using the aftermath of such appalling disaster as a metaphor for Monty's personal meltdown. For someone from L.A. or London to have done so might have felt ghoulish or opportunistic, but knowing not only that Lee loves this city but is of it makes it okay. The film swims in the mighty wake of that day, anchoring the characters very much in a particular moment when the universe itself seemed turned upside-down, when everyone felt odd and strange and like the world was over. One scene, when Jacob meets Francis in the latter's high-rise apartment, just naturally drifts over to a window overlooking the devastation of Ground Zero, like all conversations between New Yorkers in the last year and a half inevitably drift around the subject. It's hard to imagine how a serious movie like this one could have avoided it, and incorporating the worst catastrophe the city has seen in decades or perhaps ever deepens our commiseration with Monty all the more.

Perhaps only New Yorkers will feel that way. But it gives us hope that Monty is, like all New York, is a tough son-of-a-bitch who'll probably weather the toughest of situations and come out of it more bitter but also stronger for it.