The 25th Hour by David Benioff
I saw The 25th Hour years ago when it originally came out in theaters, and it just didn't quite work for me. As a result, I never would have picked up the book (I had no idea it was based on a novel) if it hadn't been for the fact that I recently read City of Thieves by the same author and adored it.
I think part of it might have been my age (I was about 18/19 when the movie came out). From what I remember, the film is an incredibly loyal adaptation but it probably helps when the author writes the screen play. Sometimes though, incredibly loyal isn't always good - what works on the page doesn't work on the screen. I think more of the problem may have been miscasting. Philip Seymour Hoffman is a good actor, I'll give him that; however, he isn't one of those actors with a baby face or one that looks much more youthful than he actually is. The character Jakob, who he portrays in the film, has a bit of a crush on one of his students. Not exactly moral or ethical but Jakob is supposed to be 26,27, and the student is 17ish. In the novel, therefore, it isn't quite as uncomfortable as when you see a 35 year old Hoffman mooning over Anna Paquin. Which actually goes beyond uncomfortable into creepy.
For anyone who hasn't seen the film or read the novel, the basic story is that Monty, a drug dealer, is going to prison for seven years the next day. He and his two best friends from high school as well as his girlfriend have one last night planned. He also has to tie up some loose ends with his old business associates. Slattery comes from the same background as Monty and now works as a stock broker with ridiculous amounts of money; Jakob is a teacher at the same private school they all went to high school (Slattery and Monty were the financial aid kids but now it is Jakob who makes the least money). Slattery, Jakob and Naturelle all have to figure out how to deal with Monty's departure and there is a lot of awkwardness and discomfort in dealing with Monty on his last night - act like nothing is wrong and have fun, or talk about? All the people in the novel seem more bond by their past than anything they currently have in common, and except for Jakob, they are less than optimistic about the future.
I definitely kept picturing Edward Norton, Dennis and Rosario Dawson while reading this book, and I want to see the movie again now since I want to see how time has changed my perspective. I enjoyed the story much more this time around, although occasionally I like knowing what's going to happen so maybe that's why.