Last Ball (2001)

After graduating high school, everyone in Jim's small town—just north of New York City—has moved on to college. Except Jim. While his friends choose Ivy League schools, he works as a cab driver, enjoying free time at the local bar and reflecting on a passionate affair with a married woman that briefly gave his life meaning. Drawing from his own experiences, first-time writer/director Peter Callahan tells a moving and often funny story about struggling to keep up when life moves forward at a faster pace than you do.