Lonesome Jim
Jim (Casey Affleck) is a perennially gloomy 27-year-old aspiring writer from Goshen, Indiana who had moved to New York City in hopes of finding success with his writing. After two years of barely making a living as a dog walker, he decides to move back home to his parents' house in Goshen.
Jim's 32-year-old brother Tim (Kevin Corrigan) is a recently divorced father of two young girls whose business recently failed. Tim has moved back into his parents' home and works in the ladder factory that's owned and operated by their father Don (Seymour Cassel) and cheerful mother Sally (Mary Kay Place). Jim has no interest in the family business and he resists pressure from Don to start working there.
Jim meets Anika (Liv Tyler), a nurse, in a bar and they end up having sex in a hospital bed, though Jim finishes almost immediately.
After a conversation between the two brothers on whose life is more pathetic, Tim, having previously made repeated unsuccessful attempts to commit suicide, drives his car into a tree. He is gravely injured, in a coma, and hospitalized. Jim finally gives in to Don and works in the factory by taking over Tim's duties. He also takes over Tim's job as the coach of a girls basketball team. The team, which has not scored a single point in the last 14 games, includes both of Tim's daughters.
While visiting Tim is in the hospital, Jim runs into Anika, who works in pediatrics. They arrange a date, but on arriving to pick her up, he discovers she is a single mother. Their relationship progresses, however. Anika is sympathetic to Jim's problems, and she decides to stand by him even when he tries to convince her that it's in her best interest to not be around him.
At the ladder factory, Jim encounters his uncle Stacy or "Stace" (Mark Boone Junior), who prefers to be called "Evil." Over a joint, Evil offers advice about premature ejaculation, and they become better acquainted. Evil offers Jim some recreational drugs and asks Jim to open a checking account for him so he can pay for things by mail. Evil gives Jim $4,000, saying it is saved-up birthday and Christmas and graduation presents.
Jim's mother, Sally, is arrested by DEA officers for allegedly shipping illegal drugs through the store's FedEx account. Evil is the drug dealer, but Jim cannot get him to confess. Evil points out that Jim will be implicated if he tries to report Evil, as he has opened an account with Evil's cash and will test positive for drug use. Eternal optimist that she is, Sally makes friends with her fellow prisoners and accepts a novel from Jim when he visits. Eventually she is released on bail.
Despite working at the factory and feeling responsible for his mother's imprisonment, Jim allows his depression to be softened by Anika and finds himself believing that life is worth living. Jim invites Anika and her son to move to New Orleans with him, but after Jim gets cold feet and makes a questionable decision, the move seems to be off the table. Jim finally decides to leave town for New Orleans by himself, leaving a note for his parents promising not to take their love for granted again and revealing Evil as the drug dealer. Anika shows up at the bus station to say goodbye. Jim departs on the bus, but as Anika drives home with her son, Jim is seen running after them, luggage in hand. He asks "for a ride" and the movie ends with Jim, out-of-breath, finally getting a bottle of water from Ben in the back seat.
=== References ===
Jim refers to the authors he admires. These authors include:
Richard Yates
Earnest Hemingway
The Sun Also Rises is shown when it is given to Jim's mom in prison.
Virginia Woolf
Edgar Poe
Silvia Plath
William Burroughs
Breece D. Pancake
Beckett
Dorothy Parker
depressing