The story revolves around a perpetual loser and slacker named Richter Boudreau (Eric Stoltz). Richter is from a privileged background in Tulsa, Oklahoma and works as a movie reviewer at a local newspaper only because his sour mother Cynthia (Mary Tyler Moore) pulled strings for him to land the job. He is dissatisfied with the direction that his life has taken; his girlfriend Trudy (Cameron Diaz) breaks up with him in the opening scene after another disastrous date, he is about to be fired any day from his job because he can't meet deadlines, he lives in a dilapidated farmhouse, he uses and sells drugs behind the scenes for some extra cash, and he is so irresponsible with life in which he has gotten so far behind on his bills that his electricity has just been cut off.
Richter also owes money to Ronnie Stover (James Spader), an abusive drug dealer who he deals with. Ronnie is married to Vicky (Deborah Kara Unger), a beautiful woman who was disowned by her socially prominent family for her involvement with Ronnie. Richter is still in love with Vicky despite having ended their relationship many years before. Vicky is the sister of Keith (Michael Rooker), a misogynistic alcoholic whose large inheritance fails to soothe his anger, loneliness, and depression. Cherry (Joanna Going) is an exotic dancer from Chicago who buys drugs from Ronnie and gets romantically involved with Richter.
Ronnie plans to blackmail Bedford Shaw (Marco Perella), the son of a socially prominent businessman named Harmon Shaw (James Coburn), after Cherry tells him that Shaw murdered her friend, a stripper/prostitute, in a motel room and that she took photographs. Ronnie attempts to involve Richter by having him hold on to a mysterious black pouch and by exploiting Richter's newspaper connections. Richter wants no part of the blackmail scheme. But he gets in over his head when Keith discovers that Richter has been sleeping with Vicky.