25th Hour (2002)

Edward Norton plays Monty Brogan, a harmless drug dealer who has 24 hours of freedom before serving a seven-year jail sentence. Nervous, confused, and terrified, Monty turns to his closest friends for support: Frank Slattery (Barry Pepper), a cocky stock broker who resents Monty for throwing his life away; Jakob Elinsky (Philip Seymour Hoffman), a hapless high school teacher who is attracted to one of his students (Anna Paquin); and Montys heartbroken father (Brian Cox), who blames himself for Montys demise. And then there is Naturelle (Rosario Dawson), Montys beautiful girlfriend, who may or may not be guilty of ratting Monty out to the cops. Monty spends his last day trying to ignore the inevitability of time, but everyone and everything only reminds him of the bleak, unpromising days that lay ahead.