25th Hour(2002)

The clock is ticking on Monty Brogan's freedom--in 24 hours he goes to prison for seven long years. Once a king of Manhattan, Monty is about to say goodbye to the life he knew--a life that opened doors in New York's swankiest clubs but also alienated him from the people closest to him. In his last day on the outside, Monty tries to reconnect with with his father, who's never given up on his son, and gets together with his two closest friends from the old days, Jacob and Slaughtery. Also in the mix is his girlfriend, Naturelle, who (or might not) have been the one who tipped off the cops. Monty's not sure of much these days. But with time running out, there are a lot of choices to be made.