A change is also looming over the head of 31-year-old Monty Brogan (Edward Norton). Caught and convicted of possessing a kilo of drugs with intent to distribute, Monty has exactly one day before he is to make his appearance at a maximum security prison, where he is to serve a term of seven years. As his two best friends, high school teacher Jakob Elinsky (Philip Seymour Hoffman) and Wall Street stockbroker Francis Slaughtery (Barry Pepper), prepare to take him out for a long night on the town as his last hurrah, Monty faces having to leave his beloved girlfriend, Naturelle Riviera (Rosario Dawson), and saying good-bye to his father (Brian Cox). More than anything, however, Monty wonders just how he could have let his life take such a wrong turn. In his eyes, he has exactly three options: go to prison and lose seven years of his life, go on the run and leave behind everyone he has ever cared about, or kill himself.

In light of the devastating events of 9/11, Americans stood their ground, announcing their refusal to allow what happened change them. As in real life, the characters in "25th Hour" falsely believe this, not realizing that they have changed. What has happened in their country, mixed with their own natural experiences, has turned them into unavoidable cynics. Francis, for example, probably correctly tells Jakob as they look out from his apartment window overlooking Ground Zero that this is the last night they will ever see Monty. Time changes people and their relationships, no matter how close, and things can never be the same in seven years as they are in the present.

Meanwhile, in a tour de force scene of shockingly harsh honesty, Monty stares himself down in the mirror, releasing a long, hateful diatribe against every race, class, and ethnicity he sees around him or hears on the news, before pointing the finger at himself. Written by David Benioff (based on his novel), "25th Hour" is especially astute to the way people think and react in life, as the cruel hands of change press down upon them.

In one of his most distinguished turns to date, Edward Norton (2002's "Red Dragon") is captivating as Monty, a kind, caring man whose unfortunate choices have cost him his life. Visiting Jakob at the same high school he once went to, Monty sees a picture of himself from when he was a star player on the basketball team, and considers the bright future he once had ahead of him. And in the present, he cares for a dog whose life he saved as a reminder of the good he has the capacity of doing. Norton gets all of the nuances and character shades just right in his portrayal of a man quietly at war with himself.

The supporting cast lend excellent support. The always-dependable Philip Seymour Hoffman (2002's "Punch-Drunk Love") gets effective screen time as Jakob, an introverted bachelor who, in a moment of carelessness at a nightclub, kisses his 17-year-old student, Mary (Anna Paquin). As the opinionated Francis, Barry Pepper (2002's "We Were Soldiers") is just fine, although his character is the most weakly written of the principles. A climactic emotional breakdown he has comes off seeming over-the-top rather than the dramatic powerhouse it was intended to be, though no fault of the actor's.

Rosario Dawson (2002's "Men in Black II") is radiant as Naturelle, a tricky role in that it is never clear until the final act whether she turned Monty in to the police, or is completely genuine in her devotion. Dawson pulls this difficult coup off like a pro. Rounding out the top-notch leads are Brian Cox (2002's "Adaptation"), as Monty's caring father, and Anna Paquin (2000's "Almost Famous"), equally soulful and childishly naive as Mary.

In a poignant alternate reality, Monty imagines what his life might be like if he were to bypass prison and go on the run. Director Spike Lee leaves the actual finale open-ended, as well as some key subplots, forcing the viewer to draw their own conclusion as to what choice Monty ultimately makes and what happens to the other characters. While this approach could have potentially been frustrating, Lee makes it work. "25th Hour," while not always hitting the bullseye, indelibly works its way underneath the skin. The key to the film's cumulative success is that it understands its characters and the flawed world they live in, and cares about them.