Tommy Basilio finds himself stuck in a downward spiral, grappling with alcoholism and the consequences it brings. After losing both his girlfriend of eight years and his job as a mechanic, he becomes a regular at the local bar, the Trees Lounge. Following the death of his Uncle Al, who operated an ice cream truck, Tommy attends the wake where he indulges in cocaine with his brother and cousins.
The night takes a wild turn when Tommy brings his relatives to the Trees Lounge, leading to a brawl between his cousin and Mike, another patron. While at a convenience store later, Tommy and Mike engage in a deep conversation about Tommy's past decisions, notably how he stole money from Rob, the garage owner who is now dating Tommy's pregnant ex-girlfriend, Theresa, casting doubt on the child's paternity.
Mike, who owns a moving company across the street from the Trees Lounge, initially declines to offer Tommy a job due to an apparent lack of need for a mechanic. Instead, Tommy decides to take over Uncle Al's ice cream route, but initially struggles to sell ice cream to kids. Things take an unexpected turn when Debbie, the flirtatious seventeen-year-old niece of Theresa, unexpectedly joins Tommy on his route, revealing that she dreamt about him.
Amid Tommy's chaotic life, Mike's personal struggles surface as well; his wife and daughter have left him due to his heavy drinking, further complicating things. Both Debbie and her friend Kelly visit the Trees Lounge, attempting to prove their legal drinking age, and Debbie claims that her "boyfriend" Tommy will vouch for her. Eventually, the group heads to Mike's house for a night of drinking, but their fun is cut short by Mike's wife's phone call asking them to leave.
As the story unfolds, Tommy and Debbie spend the night together at his place. However, upon realizing that her father, Jerry, might not accept her actions, Debbie calls Tommy, asking to stay with him. Fearful of Jerry's reaction, Tommy sadly turns her away, leading Debbie to run off with her friend Puck to New York City.
Jerry, concerned for his daughter, embarks on a quest to find her and confronts Tommy at the Trees Lounge. The next day, a tense encounter unfolds as Jerry finds Tommy outside the baseball game; enraged, he brutally attacks Tommy with a baseball bat, destroying the ice cream truck and scattering Tommy's money and ice cream, much to the delight of local children.
After Theresa gives birth, Tommy tries to make amends at the hospital. However, when he returns to the Trees Lounge, he hears about Bill, an elderly regular who collapsed and is in critical condition at the hospital. The barmaids and other patrons temporarily forget about him as they continue to drink. In a moment of reflection, Tommy sits in Bill's favorite chair, clutching a beer, and senses the reality of his surroundings and the life choices that have led him down this lonely path.
