Deciding to rescue that dog (who becomes his pet, Doyle) may be the only truly good decision Monty makes in this film. Otherwise, drug peddling (he got kicked out of a fancy high school for selling pot) and hitting on a woman who's barely legal. Yes, it works out — he and Naturelle become a couple, in what seems like a reasonably functional relationship — but, still, HIGH-SCHOOLER.
I got thinking of how several of the film's male characters are making similar decisions that are, potentially (he said gritting his teeth), not-great. Barry Pepper plays Frank, a Wall Street trader and friend to Monty. He's kept an apartment overlooking, as the film spends an entire scene pointing out, the sight of the destroyed World Trade Center. "The EPA says it's safe," he says to Hoffman's character Jacob, who's dubious. The camera looks down on Pepper and Hoffman (I miss Hoffman) through the window to the 24-hour demolition work that was being done in 2002, to clear all the damage and prepare for the future memorial, and stays looking down for a long single take. You're sure about this, Frank?
Hoffman's subplot is one that too many of my fellow guys would have come up with: Jacob's a teacher who knows a cute student (Anna Paquin) has a thing for him. A 17-year-old student, so him acting on this (spoiler, he acts on this) is illegal on top of being icky. And Monty aids and abets when he and friends head to a club and run into Paquin's character: he lets her tag along. Another bad decision, and a little later in the film I deflated a bit when Jacob makes one more bad decision. Be stronger than that, Jacob. That the subplot works at all is testament to Hoffman's and Paquin's skills.
(I prefer an earlier scene of theirs, where she visits him in the fancy school's teachers lounge. He tries to explain to her that he gave her a B- on an assignment because she can do much better work than she did, but he doesn't get to make the full argument before she assumes he's just being easier on kids he gives higher grades. But he tries to explain his reasons. I wish he'd tried harder.)
There are decisions characters make that are the "best option out of bad options" sorts of decisions; I can understand that, and empathize a little better with them. One of Monty's decisions, before he leaves New York, could have been handled laughably badly, when he asks Frank to beat him up. Fight Club crossover! If, again, this had been done badly, but the scene works. And is sad.
The film's justly famous for an internal monologue of Monty's, early on, where he rants against New Yorkers he doesn't like. It's ugly and prejudiced, and shows that he has a depth of self-loathing because he eventually rants at himself for committing the crime. Maybe he's self-sabotaged. Maybe he just didn't realize before that he was making such bad decisions, and is slowly figuring this out. In a moment near the film's end that I was surprised got me emotional and tearing up, he imagines the people he'd ranted about before, and they're still smiling at him; it's like Spike Lee's beloved New York City is telling him No hard feelings.
The film's finale is Monty getting to indulge in thinking of one more bad decision: what if he just ran? The last several minutes show a fantasy of his dad (Brian Cox) heading west instead of north, and not taking Monty to prison but instead to a small desert town, to a new life that Monty can live as long as he never returns to New York. It's an affecting sequence, wish fulfillment on top of wish fulfillment that his father pretends to justify. Of course, Monty's still going to prison; he still has seven years to survive and, ideally, behave well to cut his sentence.
Would, post-prison, Monty make better decisions? I appreciate that 25th Hour lets us know: this is on him. Maybe he would, maybe he wouldn't.