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.
Jim refers to the authors he admires. These authors include:Richard Yates
The Sun Also Rises is shown when it is given to Jim's mom in prison.
Breece D. Pancake
Casey Affleck as Jim
Liv Tyler as Anika
Kevin Corrigan as Tim
Mary Kay Place as Sally
Seymour Cassel as Don
Mark Boone Junior as Stacy a.k.a. "Evil"
Jack Rovello as Ben
The film was originally a part of a deal with Universal Studios and had a proposed budget of $3 million. However, the deal with Universal was unexpectedly cancelled and Lonesome Jim then ended up being shot and produced on a meager budget of $500,000 with the original filming schedule being reduced from 30 down to 17 days. As a cost-saving measure, screenplay writer James C. Strouse, a native of Goshen, Indiana, employed two of his nieces as actors in the film, another family member as location manager, as well he used his parents' home and factory as a location for Jim's parents' home and factory. More money was saved by recording the entire film onto a mini-DV digital video camera rather than a film camera.
During its theatrical run, Lonesome Jim never earned back its initial budget of $500,000; instead, the film grossed less than $155,000 domestically and less than $175,000 worldwide.
The film received mixed reaction from film critics. The aggregate review websites Rotten Tomatoes and Metacritic record a rating of 60 percent and 54/100 respectively as of October 28, 2008. Film critic Roger Ebert of the Chicago Sun-Times awarded the film three stars out of four, and it also received "Two thumbs up" on the film review television program At the Movies with Ebert & Roeper co-hosted by Richard Roeper. Mathew Turner of View London proclaimed "Lonesome Jim is one of the year's best films, thanks to a superb script, terrific performances and Buscemi's assured direction". Peter Travers of Rolling Stone awarded it three stars out of four, calling the film a "deadpan delight" and proclaiming "I can't recall having a better time at a movie about depression". Critic Christopher Campbell declared the film "hilarious throughout. By far it is the funniest thing I saw during the [Sundance film] festival".
On the other hand, there were a number of unfavorable reviews. Stephen Holden of The New York Times did not give the film a very favorable review, criticizing the film's sense of humor by calling it "only as broad as the Mona Lisa's smile" and criticizing Affleck's portrayal of Jim. Lisa Schwarzbaum of Entertainment Weekly awarded the film a grade of C-, writing that director Steve Buscemi "is stymied here by the inertia of his material".