The title tells the tale of Monty Brogan (Norton), a street-smart drug dealer who gets pinched by the Feds. With no way out, he's looking at a seven year bid upstate. We meet up with Monty on his last day of freedom, where he reevaluates his life, his relationship with his father (the inimitable Brian Cox) and girlfriend Naturelle (Dawson). He spends his last night of freedom in a crowded nightclub surrounded by the people he loves most. Lee's film is a somber affair, based on a novel by David Benioff, but it's also beautifully shot and incredibly well-performed. I love many of the scenes in 25th Hour -- some because they're funny, others because they're poignant and still others because they're heartbreaking. That last description basically sums up the one I want to share with you.
The scene takes place near the end of 25th Hour, on the morning of the day that Monty is set to enter prison. He's spent an evening with his friends reflecting on his life and what's to come and is now in the final stretch of his freedom. That sense of impending doom hangs over 25th Hour like a shroud, particularly in this sequence -- a perfect counter to a lovely New York morning. Monty has just given his dog to Jake (Hoffman) to keep while he's away. With that done, he turns to Frank (Pepper) and requests a favor from his childhood friend: "I need you to make me ugly." He's hinted to Frank earlier in the film that he needed a favor, and this is it. Monty's smart enough to know that if he enters the penitentiary looking normal, he's going to wind up somebody's property. His only hope to make it through those first weeks relatively unscathed is to go in looking as hideous as possible. He needs his best friend to do the deed.
Naturally, Frank isn't up for it. Monty pushes him in every way imaginable -- insulting him, accusing him of lusting after Naturelle, telling him he's not really going to be there for him and more. Frank holds his ground until Monty plays his last card and hits Jake instead. Finally, the dam breaks and Frank pummels his friend in a painfully brutal way reminiscent of Fight Club (which oddly enough, also featured Norton taking some beatings). Unlike Fincher's film, the scene here ends in tears, but also in the way Monty wanted.
Check out the clip below and if you haven't seen 25th Hour I highly recommend adding it to your Netflix queue.