Monty Brogan (Edward Norton) is going to prison, "to hell for seven years." His two childhood friends, hapless private school teacher Jakob (Philip Seymour Hoffman) and brash Wall Street whiz Frank (Barry Pepper), contemplate his bleak future. As they drink beers and argue, the camera frames them with a window in Frank's Lower Manhattan apartment, looking out on Ground Zero. Angry that Monty -- a longtime drug dealer -- lived well off "the misery of other people," Frank snaps, "Guys who look like Monty don't do well in prison. After tonight, it's bye-bye Monty. He's gone." With this, the camera cuts, at last, to show the masked workers at Ground Zero, below. Illuminated by floodlights, they rake and shovel, seemingly endlessly.

The connections between this difficult conversation and its devastating framing are at the heart of Spike Lee's 25th Hour. Just as Frank and Jake struggle over the implications of Monty's departure (or more to the point, their own anger and guilt for passively observing his descent, as well as his certain abuses by fellow inmates), so does New York City (and by extension, the nation and the world) continue to contemplate Ground Zero, to mourn and debate its meaning.

That Lee's movie sets Monty's individual story against this almost unfathomable backdrop is only one of its audacious ambitions. Gorgeously shot on digital video by Rodrigo Prieto, with a screenplay adapted by David Benioff from his novel (published in 2000), the film cuts between Monty's last day and the incremental events that brought Monty to his unbearable present.

First he visits his retired fireman dad, James (Brian Cox), now owner of a bar: One wall is adorned with pictures of real-life members of the fire department's Rescue 5, James' unit, who died on 9/11. While James guiltily believes his past alcoholism and debts pushed his son into dealing, Monty harbors his own rage and self-hate.

In the bar's bathroom, he confronts himself in the dingy mirror, projecting his dread and fury onto all the "assholes" he can think of, aiming a series of "Fuck you"s at Sikhs and Pakistanis, Chelsea boys, the Catholic Church, the federal government, terrorists, Russians in Brighton Beach, black "brothers," Korean grocers. All come right back at him, fronting just like him, lashing out, feeling victimized and weak. Frequently compared to the similarly framed epithet-tirade sequence in Do the Right Thing (1989), this set piece is even more awful: The same sentiments are equally relevant some thirteen years later, making it a bleak backdrop -- as well as a response -- to 9/11.

Monty also directs his resentment at his girlfriend, Naturelle Rivera (Rosario Dawson), suspecting she turned him in to the feds. His paranoia is tempered by a complex, genuine love, revealed in flashbacks to their life together and to their first flirtation -- he in a black leather jacket, she in her schoolgirl uniform -- which takes place on swings in a park near her school, where he's selling drugs. Charming at the same time that it's insidious (she's 17, says she's 18; she's Rosario Dawson, he's willing to hear the lie), this budding romance will end badly -- you already know he's going to jail.

Before the end comes a last bash, a party at the swank nightclub owned by his Russian drug-lord employer. This sequence throbs with dark, desperate energy, sweaty bodies driven by narcissism and need. Here Naturelle meets another schoolgirl, her seeming opposite: Jake's student, Mary (Anna Paquin), is confident, naive and all too willing to sex up her teacher for a better grade.

The clubbish frenzy has the protagonists splitting off to undergo separate rows and revelations. But it's the next morning -- the 25th hour -- when Lee's movie delivers its most potent insights into what all this frenzy aspires to: hope, safety, self-possession. First, Monty, ever the manipulator, engineers his own punishment as a means to survival, a reckoning as brutal for his friends as for him, exacting a cost for their own past passivity.

And second, James narrates an alternative future while he's driving his son to prison. The sequence stretches out into a rural, mythic "America" that these die-hard city dwellers have never known, a reverie set in the desert where Monty doesn't go to prison. The images tumble forward into a future that might (never) be: Monty and Nat's wholly integrated, wholly ordinary and extraordinary family (none of its members resemble him, suggesting that he's given up his fears of "visible" otherness). Just think, James says, Monty sleeping in the car beside him, you'll look back and say, "It all came so close to never happening."

The story James tells is simple, profound and outrageous, and it speaks the lessons available at Ground Zero. It's not about vengeance or violence, but benevolence and real courage. Stunningly, the movie doesn't resolve its own ending, doesn't let on what choice Monty will make. 25th Hour takes its time, especially in this last narration, and if it occasionally stumbles, making some points too emphatically, it is, in the end, a generous and reflective, uncommonly urgent and resonant film.