Tommy (Steve Buscemi) is a loser. He frequents the Trees Lounge bar with the other regular low-lifes. He lost his job as a mechanic, as he 'borrowed' some money and couldn't put it back. His ex-girlfriend is now his ex-boss's girlfriend. He meets Mike (Mark Boone Junior) along the way, who owns a fleet of removal trucks, but finds hanging around the bar and taking cheap drugs a better use of time.
Uncle Al who owns an ice-cream van dies at the wheel and Tommy finds a new day job. Driving around the streets he meets his ex-girlfriend's sisters's daughter Debbie (Chloë Sevigny). She's 17 and after a night of drink and drugs, she spends the night at his house. Her father Jerry (Daniel Baldwin), eventually finds out and isn't pleased even though 'nothing happened - I swear!'. The film ends as it started with Tommy on a bar stool at the Trees Lounge, but something's different.
This is a gentle comedy with a straight-forward story written by Buscemi. He wrote himself a great role and the direction is superb. Tommy is essentially at the start of his alcoholic career and the bar stool he sits on at the end is significant. Much of the film is spent watching the sad interaction between people who have known each other years, but it doesn't become maudlin.
The characters are all small town America and the casting excellent. Chloe Sevigny often seems to be playing herself in these early roles. Samuel L. Jackson turns up in a bit-part as a truck driver and Carol Kane is the bar service. Music by Evan Lurie.