Edward Norton plays Monty Brogan (named after Montgomery Clift, so we're told), a pleasant looking Irish-American New Yorker, exuding a spoiled aura never quite explained, who we learn right away has a heart of gold when he rescues an abused dog in the opening scene. This act of kindness has little connection with the tension-filled countdown before Monty heads off to prison, when he calls upon his friends, Jacob Elinsky (Philip Seymour Hoffman), a frustrated high school teacher petrified of his attraction to his youthful students, and Francis Slaughtery (Barry Pepper), a brash, cocky Wall Street investor. That these disparate young men have remained friends from childhood is something of a stretch that, instead of demonstrating New York's diversity among the white middle-class, never feels credible.
More interesting is the kinetic relationship between Monty and his live-in girlfriend Naturelle Riviera (Rosario Dawson). Despite her clear devotion, Monty suspects Naturelle of ratting him out, a suggestion placed in his head by a member of the Russian mafia for whom he dealt drugs. The film's major conflict rests on the slender thread of whether or not Monty will ever be sure of Naturelle. The film's weakest moment is the mafia element in scenes that swerve dangerously close to farce.
Also compelling, but more confused, is Monty's relationship with his father (Brian Cox), a retired fireman who owns a pub rescued from bankruptcy by Monty's ill-gotten gains. Dad seems oddly blithe if sincerely saddened by Monty's conviction and can only offer his son a weird, if not completely implausible, last-minute out. His connection with the New York fire department leads helmer Lee to an ill-advised link to the World Trade Center tragedy that goes nowhere. Whether Lee is attempting to associate Monty's cavalier irresponsibility with America's over-confidence leading to destruction or something more personally pointed is lost and out of sync with an already meandering tale.
Norton's well-known talents are somewhat muffled by writer David Benioff (adapting his own novel) and Lee's inability or unwillingness to explore Monty's contradictory nature. Instead of explaining Monty's choice of peddling dope, Benioff and Lee appear to feel the real drama lies in everyone else's guilt. From Monty's father to Naturelle, who benefited from Monty's high life, to Frances and Jacob, who never questioned their friend's actions, all are presented as equally to blame for Monty's failure. While a legitimate story aspect, the mass-guilt thing isn't developed enough and serves only to rob Monty (and Norton) of more substance.
It's notable that the one memorable sequence that rings with Lee's touch features Monty angrily lashing out at New York's various ethnic tribes, but, like too much of everything in the film, the moment is really apropos of nothing. Starring Edward Norton, Philip Seymour Hoffman, Barry Pepper, Rosario Dawson, Anna Paquin and Brian Cox. Written by David Benioff. Directed by Spike Lee. Produced by Spike Lee, John Kilik, Tobey MacGuire and Julia Chasman. A Buena Vista release. Drama. Rated R for strong language and some violence. Running time: 134 min