Richter Boudreau (Eric Stoltz), a perpetual loser and slacker from a privileged background in Tulsa, Oklahoma, is on a bad streak after being fired from his job as a movie reviewer. He owes money to Ronnie Stover, an abusive drug dealer he deals with, and is still in love with Vicky Michaels Stover, the wife of Ronnie's partner. Richter gets manipulated into a blackmailing scheme by Ronnie and his brother Keith (Michael Rooker), a misogynistic alcoholic whose inheritance fails to soothe his anger.