25th Hour (2002)

Set in the aftermath of 9/11 in New York City, Monty Brogan faces the reality of a seven-year prison term for drug dealing. In his final hours of freedom, he spends time with his loyal friends, reflecting on life and grappling with the choices he's made. As he tries to emotionally prepare his girlfriend for his long absence, Monty confronts the weight of his decisions and the uncertain future that awaits him.