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25th Hour, 2002

Monty (Edward Norton) is a mid-level drug dealer who has been caught, tried, and convicted. With just one day left before he must report to prison, Monty spends the day with his girlfriend Naturelle (Rosario Dawson), as well as his childhood friends Jacob (Phillip Seymour-Hoffman) and Frank (Barry Pepper).

Grounding its narrative in a highly specific post-9/11 New York, this film is a powerful study of place with a so-so set of character arcs.

There are plenty of films where one can remark that the setting--often a city--is practically a character in the movie. In this film, that’s taken to an extreme, as Monty’s last day in New York involves a hyper-awareness of the people and places around him. And in this film it isn’t merely the place, but also the time. Jacob and Frank have a conversation overlooking the site of the Twin Towers, watching as construction vehicles navigate around. They talk about rumors that the air is still toxic. A wanted poster for Osama Bin Laden hangs in Frank’s stock-trading workplace. The melting pot of the city is tinged with anti-Mulsim/arab sentiment.

The shadow of 9/11 is echoed in an interesting way in the position where Monty finds himself. Going to jail is a disaster that Monty can see coming. He is acutely aware of the before, and while he doesn’t know the exact details, he does know that nothing after will be the same. He anticipates damage, possibly permanent, and that certain potentials will be gone forever. Is it better or worse that he can see what is coming?

This weight of anxious anticipation hangs over the whole film as Monty must process what his future holds. Again and again he expresses fear that he will be a victim of sexual assault and physical assault in prison. Other characters offer him strategies for survival, but he is unable to shake his concerns. Every minute that he spends with Naturelle, he is aware that he will be away from her for the better part of a decade. Plans that they had for having children together have been derailed, if not entirely scuttled. He’s also connected to some very dangerous men, and so he must tread carefully in terms of them believing that he hasn’t informed on them to the police.

In its best moments, this film balances Monty trying to soak in the city around him with the encroaching dread about his upcoming incarceration. In a long monologue delivered to a mirror, Monty tries to cast the city as a vile place, spewing hatred at just about every subgroup he can name. But at the end, he cannot keep up the facade and turns his loathing on his own reflection. Every moment of enjoyment---every drink, every dance, every hug, every kiss---is tinged with an unspoken “for the last time”.

Spike Lee shoots New York with an intimate familiarity that captures the beauty and the everyday grunge of the place. He places Monty strategically in ways that both capture the hustle and bustle of the place and simultaneously make Monty feel impossibly alone.

Where I didn’t really engage with this film were in the various subplots. Jacob spends the whole film waffling and sweating over whether to romantically pursue one of his teenage students, Mary (Anna Paquin). I’m sure you can guess my feelings about this “dilemma”: it’s gross! And unethical! And frankly, watching the way that Jacob’s friends egg him on---including getting Mary into a nightclub despite her being underaged---broke my sympathy for any of them.

From a character point of view, I was most drawn to the dual feelings of anger felt by Monty’s friends and Naturelle: they are angry at him for getting caught, but they are also angry at themselves for standing by while he went down that path. Frank confronts Naturelle about the fact that she’s been benefiting from Monty’s dealing. Even Monty’s father must grapple with the fact that Monty started dealing in the first place to help him pay off his debts. It’s very clear that Monty is a smart and charismatic person, but he was never strongly steered in a more lawful direction by any of the people in his life.

I did have some mixed feelings about the portrayal of Monty, which uses some too-obvious manipulation to get us on his side. The very first time that we encounter Monty, he is rescuing a dog that has been badly abused and abandoned on the side of the road. Monty nurses the dog back to health and adopts it. I mean, come on. Monty’s crimes are also abstracted to some drugs hidden in his couch. We never see any of the results of his drug dealing, or even really see the impact of drug usage in the city. I can easily empathize with Monty’s fears and his despair over his squandered potential, especially when his arrest is really just a tactic to shake down his boss. But at the same time it feels somehow dishonest to present Monty as almost an innocent victim, when his actions have at the best furthered addictions and at worst killed people.

I wish I’d been more engaged by the various characters and subplots. It’s not just a matter of them being unethical people, but they are unethical people who are also kind of boring. Once the action moved to the nightclub, my interest really took a nosedive. A stunning final sequence between Monty and his father (Brian Cox) ends the film on an emotional high note and pulls everything back together.