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Long Island loser Tommy (Steve Buscemi) is a hopeless alcoholic who loses his job for stealing from his boss, Rob (Anthony LaPaglia), who's now dating his ex, Theresa (Elizabeth Bracco). Tommy copes with his failures by hanging out at local dive Trees Lounge with friends he can barely stand. He takes a gig as the ice cream man, but he's awful with kids. The best thing in his life is a lukewarm romance with cool local girl Debbie (Chloë Sevigny), who, unfortunately, is Theresa's underage niece.