25th Hour (2002) Spike Lee

Monty Brogan is about to start his last day of freedom before turning himself into the authorities and serving a seven-year term for drug dealing. He's a charming young man who had always dreamed of being a fireman, following in the working-class footsteps of his father, who has had to put up his bar in Queens as bond so that his son can stay out of jail until his sentence begins. Monty, named for Montgomery Clift, does not know how he managed to get himself into this predicament. It was easy money and it carried so many perks, and you'll feel more than a little sympathy for this young man who has managed to kill his own dream for courtside seats at Madison Square Garden. But before he goes to prison, Monty wants to have one last night out on the town with his two best friends. Frank Slattery is a bond trader, one of the best and most successful risk takers in a very risky business. The other is Jakob Elinsky, an English teacher who envies his friends' lifestyles but who has no intention of ever giving up his job for the easy money, despite the disillusionment of teaching high school students in a tough school. The three young men enjoy the night into the early morning as they eat, drink, and visit the hottest spots in town. It's a sad night for Monty, but he has a plan that neither Frank nor Jacob know about--and it makes for a shocking ending to this brilliant and disturbing story.