Having seen his dreams of becoming a published author crumble in New York City, 27-year-old Jim (Casey Affleck) takes a deep breath, gives up his menial job of walking dogs, and returns to his home in a small Indiana town. He doesn’t really like his family but he has no other options. His mother, Sally (Mary Kay Place), loves him dearly; his dad, Don (Seymour Cassel), runs a ladder factory with her. Jim's older brother, Tim (Kevin Corrigan), works for their parents and is saddled with two daughters who have convinced him to coach their basketball team. For Jim, the only good thing about being home is knowing that Tim's life is more screwed-up and hopeless than his own. He tells him so and the consequences are shocking: his brother drives into a tree and ends up in the hospital with two broken legs.

Jim reluctantly agrees to take Tim's place at the ladder factory where he meets a self-absorbed man who likes to be called Evil (Mark Boone, Jr.), which is appropriate since he's selling drugs. In just another one of a string of bad decisions, Jim opens a checking account for Evil in his own name. He is shocked when the Feds arrive at the factory and arrest his mother for drug dealing. The only bright spot in Jim's downward spiraling life is his blooming romantic relationship with Anika (Liv Tyler), a nurse and single mom. Her young son is thrilled when Jim, now the coach of the girl's basketball team, lets him tag along to practices.

Lonesome Jim is the kind of loosely-structured and quirky film we have come to expect from director Steve Buscemi. (Trees Lounge, Animal Factory). He has a way with actors that draws out the best in them. The screenplay by James C. Strouse eventually focuses in on the intimate relationship between Jim and his mother. They are total opposites. She is perpetually cheery. He has spent a lot of time reading authors who emphasize the dark side of life; he runs through a list of his favorites for Anika and most of them committed suicide.

Jim doesn't take well to his mother's exuberant expression of love for him; she certainly has a higher regard for his potential than he does. When she is arrested and taken to prison, she immediately makes friends with other women there. Sally's optimism and kindness eventually seep into her son's wayward soul, and he is forced to recognize her goodness. Once he thought that she was nothing more than a joke with her emotions; now enmeshed in a relationship with Anika and her son, Jim realizes that his mother's kindness is a precious gift that is worth honoring and emulating. This mother-son connection, so rarely explored in films, comes across loud and clear.