Jim (Casey Affleck) is a perennially gloomy 27 year-old aspiring novelist from Goshen, Indiana who 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 and no success with writing, he defeatedly decides to move back home to his parents' house in Goshen. Jim's 34 year-old brother Tim (Kevin Corrigan) is a recently divorced father of two young girls whose business recently failed. Tim has never left his parents' home and he works in the ladder factory that's owned and operated by their pessimistic father Don (Seymour Cassel) and overly cheerful mother Sally (Mary Kay Place). Jim has no interest in the family business and he resists pressure from Don to start working there. After an argument between the two brothers on whose life has been more pathetic so far, Tim, having previously made repeated unsuccessful attempts to commit suicide, drives his car into a tree in hopes of ending his life; he is gravely injured and hospitalized. Jim now finally gives in to Don's pressure to work in the factory by taking over Tim's duties who isn't able to work. 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 Tim is in the hospital, Jim finds out that Tim's nurse is Anika (Liv Tyler), a good-hearted single mother with whom Jim had a brief sexual encounter in the past. Anika is sympathetic to Jim's problems, whether real or perceived, and she decides to stand by him in encouragement even when he tries to convince her that it's in her best interest to not be around him. At the ladder factory, Jim is introduced to his uncle Stacy (Mark Boone Junior). Stacy is a drug dealer who prefers to be called "Evil" and sells drugs in the factory. Being somewhat impressed by Evil's demeanor, Jim tries to help him with his drug dealing business but with disastrous results. Believing Sally to be the drug dealer, the police arrest and imprison her. The eternal optimist that she is, she finds happiness in her new surroundings and makes friends with her fellow prisoners. Despite working a job he hates and feeling responsible for his mother's imprisonment, Jim slowly allows his monumental depression to be dismantled by Anika and finds himself believing that life is better than what he had believed it to be so far.