8) 25th Hour
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Edward Norton and Spike Lee don’t do many kids movies, and it’s safe to say Philip Seymour Hoffman didn’t make a great deal of them either. Lo and behold though, the 2002 collaboration between the three, 25th Hour, is a chilly, cerebral affair, a bleak, character-driven New York drama that has the potential to ruin your day.
The film’s focus is Norton’s Monty Brogan, a man who parties away his last day of freedom before he’s set to embark on a seven-year jail stretch for dealing drugs. Along with him is Hoffman’s school teacher, who has a crush on – and ends up making out with – one of his 17-year-old students. Also, Barry Pepper beats Norton to a pulp.
If you’re looking for a fun time, this isn’t the film.