A young prostitute named Elizabeth (Renée Zellweger) is brutally murdered. Detectives Phillip Braxton (Chris Penn) and Edward Kennesaw (Michael Rooker) have only one suspect: James Walter Wayland (Tim Roth), and he seems to be a long shot. While he had paid visits to Elisabeth before her death, he is also a very rich man and sort of an academic genius. But, as is to be revealed in the course of three days of intense interrogation, his dark side, one of a compulsive liar and heavy drinker, lurks beneath the surface. However, the two detectives have their secrets too - one is deep in gambling debts and another has sadistic streak. As the hours slowly pass by in a dark interrogation room, Wayland, the deceiver, tells his story...