In his first directorial effort, the guy-in-every-indie-film-with-the-big-eyes-and-the-bad-teeth Steve Buscemi, plays Tommy, an unflattering semi-autobiographical portrayal of a directionless alcoholic. This film is to alcoholism as "Trainspotting" was to heroin abuse, painting the grim portrait of the chronic drinkers who waste their time and destroy their lives in a Long Island watering hole called the Trees Lounge. While it is an interesting and somewhat poignant journey that Tommy undertakes, like "Trainspotting", "Trees Lounge" suffers from its often directionless travelogue narrative, which barely comes to some kind of a cohesive resolution after ninety-eight minutes.
Tommy is a 31 year old who recently lost both his auto mechanic job and his girlfriend of eight years, Theresa (Elizabeth Bracco). And now, Theresa is pregnant, possibly with Tommy's child, and married to the man that fired Tommy, Rob (Anthony LaPaglia). As we watch Tommy stumble in a dullard's daze, trying to find another job (he can't even repair his own car) and reconcile with Theresa, he comes into contact with an odd collection of characters. Bill is an aging alcoholic who sits in the same seat at the Trees Lounge every day and is only coherent for a few seconds at a time, a representation of what Tommy does not wish to become. Mike (Mark Boone Jr., who would do an excellent job playing Barney if a live-action "Simpsons" movie was ever made) is another Trees Lounge deadbeat who owns a moving business, but prefers to spend his days at the bar, while ignoring his wife and daughter. After Tommy's Uncle Al dies from a heart-attack, Tommy takes over his ice cream truck business, and like everything else, he screws that up too. As he cruises around the neighborhood, consistently missing the same boy who wants to buy an ice cream from him, Tommy comes to know Debbie (Chloe Sevigny, last seen in "Kids"), the seventeen year old daughter of Theresa's sister.
Tommy is a pathetic loser that is desperately grasping at straws to stay afloat, but everything he does only sinks him deeper into the hole he has dug himself. As the film progresses, Buscemi reveals the subtle connections between the different characters and provides a few memorable moments (such as Uncle Al suffering a heart attack while driving the ice cream truck, and the sexual tension between Tommy and Debbie). However, these gee-whiz moments are too scarce to maintain one's attention to the meandering story. It is a dialogue-driven story, but unfortunately, very little in terms of memorable or profound dialogue is uttered by the characters.
Unfortunately, by the end of the film, Tommy still has not come to the fundamental understanding that he must stop his drinking first, instead of waiting for a reason to stop drinking. Which is indicative of "Trees Lounge", which takes you on a meandering journey with Tommy to who knows where.