Last Ball (2001)

High school is over, and everybody in the small town just up the Hudson from New York City where Jim lives has made plans and moved on. Everybody except Jim. While his buddies head off to one Ivy League college or another, Jim rejects their upwardly-mobile choices and takes a job driving for the local cab company instead, which allows him plenty of free time to hang out, drink with the locals at John's Bar and Grill, and think back on the love affair with a married woman that, for the exquisite moment it lasted, brought passion and meaning to his life. Drawing partially on events from his own life, first time writer/director Peter Callahan tells a poignant and sometimes hilarious story about what happens when life moves on and you're not quite ready to move with it.