8. The 25th Hour
One of Spike Lee's best films, 25th hour is a story of the last 24 hours of Monty Brogans life as a free man. Sentenced to seven years in prison for dealing drugs, Monty spends his last night of freedom hanging out with his oldest friends and girlfriend, while also trying to find out who ratted him out to the police. At the end of the film, Monty's father is driving him to prison, setting the stage for arguably the films best scene. Desperate to keep Monty out of prison, his father regals Monty with a beautiful fantasy in which Monty runs away to make a new life for himself in a remote midwestern town. After the fantasy ends, the car continues on its course towards the prison, showing that Monty has accepted his fate. Filled with a sense of regret, and with most of the characters lamenting lost opportunities, 25th Hour is undoubtedly a bit of a downer. The ending of the film on the other hand is intentionally a bit more ambiguous. While Monty begins a seven year prison sentence, leaving his girlfriend and father to support themselves, his decision to face his judgement shows that he might have turned over a new leaf and just maybe, when he gets out, he'll be able to live out his father's fantasy anyway.