The harrowing event in question concerns Monty Brogan (Edward Norton) having been arrested for possession of narcotics. Once the story begins, Brogan has already been sentenced to a lengthy prison sentence that will begin in one day's time. This means the plot concerns itself primarily with the last 24 or so hours before Brogan has to go to jail with occasional flashbacks to the day Brogan was arrested. We follow Brogan as he comes to terms with his impending stay in incarceration as well as how this turn of events is impacting the people in his life, including his girlfriend Naturelle (Rosario Dawson) and his two best friends, High School teacher Jacob (Phillip Seymour Hoffman) and Wall Street broker Frank (Barry Pepper).
25th Hour is a movie about Brogan and his loved ones coming to terms with a new reality just like how both New Yorkers and America at large was grappling with a redefined definition of normal existence in the wake of 9/11. Among the many ideas it explores in depicting this process of coming to terms with an altered status quo is how exactly Brogan is coping with his impending prison sentence. Brogan is depicted as a multi-faceted individual, neither a hero nor a villain. A prologue for the story shows his compassionate side by depicting him saving a dog that's been left to die but in getting caught for his crimes, he's also shown not to be a victim of bigger tragic circumstances or being at the wrong place at the wrong time. He simply got caught doing something illegal for personal gain.
Thus, Brogan's process of coping with his impending stay in prison is similarly complex and cloaked in moral shades of grey, a fact that's emphasized by one of the most memorably realized sequences in 25th Hour depicting Brogan's reflection in a mirror going on a tirade against every minority group in New York. This is the side of Brogan that wants to respond to his own mistakes simply by lashing out at others, there has to be some kind of marginalized community he can focus all of his rages on. The editing in this scene by Barry Alexander Brown is astonishingly executed with its rapid cuts from one minority group to the next that visually reflect how this diatribe is a fast-paced stream of consciousness for Brogan. There is no time in his polemic screed for pauses and the editing beautifully reflects this in a visual format.
This outstanding sequence serves as a great example of how well 25th Hour depicts people's messy processes of coming to terms with personal tragedies. Nobody in this story has the concrete answers for how to react to Brogan's situation, least of all Brogan himself. The intentional lack of concrete answers is one of the best parts of David Benioff's exceptional screenplay which is especially great at using individual distinct characters to explore the varying ways human beings can process tragedy. This is most notably seen in a conversation between Jacob and Frank that sees the two arguing over a more optimistic and pessimistic, respectively, outlook on what will happen to Brogan during his stay in lock-up. 25th Hour doesn't want the viewer to walk away thinking either of these perspectives on their own has all the answers, rather, it simply wants this particular exchange to depict just how many different perspectives can emerge from being impacted by the same event.
The way the past can impact the present isn't the only interesting way 25th Hour fascinatingly tackles the concept of time. In one of its most interesting visual flourishes, sequences set in the past, like an initial meeting between Brogan and Naturelle or a depiction of the night Brogan is arrested, are filmed in a manner that emphasized exceedingly bright lighting and more vibrant colors compared to the intentionally drab present-day sequences. It's like these flashback sequences have been plucked from the mind of Brogan whose chosen to make his memories of certain events as pristine looking as possible. Meanwhile, the present, a point in time he has no control over, has more realistic cinematography to reflect the level of grim reality intruding on the life of Brogan.
Every scene in 25th Hour has some level of visual and thematic subtext that makes it, like many of Spike Lee's directorial efforts incredibly fascinating to ponder and the various performances carry a similar level of thoughtful heft to them. Edward Norton gives one of his best lead performances in depicting Brogan in a morally complicated fashion that feels like a perfect companion to how the character is written while Phillip Seymour Hoffman, a gifted performer in the realm of morally complex people, is in his element tackling the character of Frank. Matt Dillon also brings welcome layers to the part of an abusive Wall Street broker that's typically depicted a caricature in most of American pop culture.
Meanwhile, Brian Cox delivers outstanding work as Brogan's father, James, particularly in the final scene of 25th Hour, which concerns James telling his son how he could potentially avoid turning himself into the authorities. 25th Hour has been concerned with how the past impacts the present for all of its story but in this closing scene, we get to see this film turn its attention to the future and its vision of the future is both written and shot in an idealized fashion reminiscent of the various flashback sequences. Cox's wistful voice-over narration in this scene is responsible for a great deal of the emotional impact of this glorious sequence and it provides a fittingly captivating conclusion to 25th Hour.
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