As of the writing of this review, two films have touched upon the events of 9/11. Brown Sugar, the first film to go into production in New York after the events showed a brief image of the twin lights commemorating the World Trade Center. The Guys deals explicitly with the aftermath of the events, but will be too specialized to receive a wide release. So for most people, The 25th Hour is their first experience dealing with the terrorist events on film. Given the subject of The 25th Hour, adapted by David Benioff from his novel, it seems an appropriate use of tragedy by director Spike Lee. The film takes place over one day, the last day for drug dealer Monty Brogan (Edward Norton, Red Dragon, Frida). Brogan is going to jail, and must sort out all the loose ends of his life before he goes. It is a meditation on his mortality, with the dual events of jail and the WTC bombings forcing Brogan to face his mortality.

Lee's (Bamboozled, The Original Kings of Comedy) is to examine the lives of Brogan and the people around him. Jail is forcing all of them to take stock in what is important to them. He does this on a superficial level, which causes the entire movie to suffer. One does get a decent sense of Brogan by the end of the film, but not everybody else. At over two hours, there is a little too much time and not enough plot to sustain a sense of momentum. The climax of the film comes at a party that Brogan is throwing for him and his friends. At the same time, he needs to put to rest his past and deal with the drug dealers he used to associate with. His girlfriend Naturelle (Rosario Dawson, The Adventures of Pluto Nash, Men in Black II) is worried, since Brogan has been distant. He is suspicious that she is the one who turned him in.

Brogan's friends are much more pragmatic about the whole affair. Frank (Barry Pepper, Knockaround Guys, We Were Soldiers) feels bad for Brogan, but also realizes that Brogan is getting what he deserves. Frank is an interesting character, but Lee fails to explore him to a better extent. As the night draws on, the fact that he knew but did nothing weighs heavily on him. By saying something, he could have prevented this. Their other friend Jakob (Philip Seymour Hoffman, Love Liza, Red Dragon) is infinitely duller. He is a teacher, infatuated with his high school student Mary (Anna Paquin, Finding Forrester, X-Men). To Jakob, Brogan's impending incarceration is a wake-up call for him to break out of his shell and carpe student. Brian Cox (Adaptation, The Ring) comes in a little too late as Brogan's father. He owns a bar, and indirectly encouraged Brogan's drug dealing long ago. He is another fascinating character that Lee fails to delve into.

Everything is heading towards some sort of rebirth for each character. Forcing them to reevaluate their lives will hopefully make them change for the better. However, this change never really happens. Well, it does, but not in a satisfying way. The 25th Hour just goes and goes, examining its characters a little too slowly. There are also some extended flashbacks that don't really shed any new light on each person, but do provide some context for the various relationships. This was an interesting concept, but one that didn't quite gel completely.