What separates 25th Hour from this pack is not it's box office - it only made $13 million during it's limited run - but rather the timing of its release and the way it handles its subject material. The film came out in December of 2002, a little over a year later, and was one of the first films to address post-9/11 New York (sure, you could make the argument that last-second edits made Spider-Man the first, but that falls mostly into the never-again, rah-rah U-S-A patriotism of the time). The handling of the subject material is unique in that, though it does make overt references to the incident - the opening credits featuring the lights that stood in place of the World Trade Center, a scene set looking down into Ground Zero, the infamous bathroom mirror scene (more on that below) - it mostly uses the narrative action to capture the atmosphere of the time.
As far as narrative action goes, not a lot actually happens in the film. It's the last day of freedom for Monty Brogen (Edward Norton), who's going to prison for heroin possession and sale, and he tries to make the most of his final hours. He spends time with his girlfriend, Naturelle (Rosario Dawson). His best friends, Frank (Barry Pepper) and Jacob (Philip Seymour Hoffman), take him out for a night on the town. He settles his "debts" with the Russian mob and with his somewhat-estranged father (Brian Cox).
What the film lacks in active narrative it makes up for in atmosphere and aesthetic. Written by David Benioff (perhaps now best known as a co-creator of HBO's Game of Thrones) and based on his novel, the film functions, on a script level, as a contemplative examination of freedom and the consequences of the choices we make. However, director Spike Lee uses it as an expression of post-9/11 confusion, a mix of rage, depression, and fear that permanently damaged the New York psyche. The aforementioned mirror scene is a perfect five-minute distillation of this: it's simultaneously an explosion of anger and a celebration of what makes New York great. The film manages to maintain this tone throughout, thanks to Lee's masterful direction. This is, without a doubt, his best film of the 2000s.
As to be expected, the performances are phenomenal. Norton is characteristically great as Monty, naturally convincing as a good man who's made some bad decisions. Hoffman plays Jacob as a meek schlub of a high school English teacher, fighting his inappropriate feelings for one of his students (played by Anna Paquin), while Pepper's Frank is a slick, flashy stockbroker with a good heart underneath, earning your sympathy. Dawson's role doesn't require to do much, but she makes the most of it and leaves a startling impression of loyalty and support.
25th Hour is a lyrical, powerful testament to the atmosphere in New York - and America - after the terrorist attacks of 9/11, disguised as a story about a man facing prison for his crimes. It's an incredible film, deserving to be seen by anyone curious about the time period or Lee's filmography. A