Adapted for the screen by David Benioff from his novel, 25th Hour is the story of Monty Brogan (Edward Norton), a nice-looking, polite and articulate New Yorker in his late 20s. We first meet him performing an act of kindness as he rescues an abused and abandoned dog. In addition to his bartender father James (Bryan Cox), Monty has three good friends: two old high school chums -- Frank Slaughtery (Barry Pepper), a handsome but arrogant, big-time Wall Street trader, and Jakob Elinsky (Philip Seymour Hoffman), a shy, rumpled high school literature teacher -- and Naturelle Rivera (Rosario Dawson), his beautiful Puerto Rican girlfriend. Monty's attachment to Naturelle is captured in his confession to Frank that she's the only woman he continued to fantasize about even after he slept with her.
James says of Monty that he had the intelligence to be anything he wanted, even a doctor or lawyer, and we have no reason to discount the father's judgment. But Monty's mother died when he was a teen, and James fell into an alcoholic haze from which he didn't emerge for more than a decade. In high school Monty began to get in trouble. If he started college, he didn't finish. Instead, he began to deal drugs. Crime made Monty very prosperous. He contemplated for several years getting Frank to launder his dirty money in the stock market and retiring to a life of leisure on his investment earnings. But he didn't do it, and now he never will. Someone ratted him out. He's been busted and convicted. Tomorrow he begins a seven-year prison term.
Lee and Benioff sustain the tension here with conventional narrative techniques. Who turned Monty in and why? Did his father do it to get him off the street before he gets killed? Did Frank or Jakob bear him some ancient grudge? Though Monty can barely admit the suspicion, he worries that Naturelle fingered him. She knew where his cache and stash were concealed, and when he was arrested, the DEA agents went right to his hiding place. Did the feds threaten to indict her too if she didn't give him up?
But the filmmakers are only incidentally interested in identifying the film's traitor. Their primary concerns are character psychology and the disproportional fate that awaits Monty. We know Monty regrets what he's done with his life, but it's not clear that he's actually ashamed of dealing drugs. He wishes he'd gotten out when he might have. He rues the greed that eventually got him caught. Frank believes that Monty deserves what lies in store for him because he got rich helping people ruin themselves. But Monty never overtly deals with the implications of selling people poison. And when a foul, strung-out junkie approaches Monty for a fix, Monty treats his former client not with compassion but with contempt.
Still, Monty is correct in his unspoken conviction that he never made anyone take drugs and that if he hadn't supplied his clients, someone else would have. He never committed an act of violence. So how different is he from those who won't be going to jail? Frank has the mentality of a gambler; only he uses other people's money to fuel his thrill seeking. Jakob has a Humbert-Humbert-like attraction for one of his lit students, an underage vixen (Anna Paquin) whose flagrant sexual posturing belies a naive vulnerability. She needs a caring parent, not an adult lover. James allowed his son to bail out his bar with money he knew was soiled. And Naturelle lived the good life on drug booty. She may or may not have turned Monty in, but she evidently never urged him to quit.
But come tomorrow, the others will go on with their lives while Monty will go to prison, where the picture makes clear he will be raped or will have to fight viciously to keep from being raped. Heretofore, though he has lived outside the law, Monty has had it soft. Tomorrow that will end. His time will be hard, and even if he survives, he will know only the bleakest future. He will be approaching 40 when he gets out. He will have no job skills. He will return to crime only at the risk of a life sentence as a multiple offender. And here is what is so very smart about this movie: Without making Monty a hero in the slightest way, without romanticizing his courage or trying to excuse him as a victim, the film wonders if our society hasn't gotten things seriously out of whack, hasn't devised a system making things worse rather than better.