From acclaimed playwright David Mamet, “You are not where you belong,” says the fortuneteller, and Edmond (William H. Macy) begins his descent into a darkly funny yet horrifying modern urban hell in this compelling film, written by David Mamet and directed by Stuart Gordon. The encounter with the fortuneteller has caused bland businessman Edmond to confront the emptiness of his life and marriage. His wife (Rebecca Pidgeon) complains that the maid broke a lamp, and this seems to be the last straw, prompting him to flee the safe boredom of his home for the vortex of the dark streets of the city.

The strangely liberating act of leaving his wife tilts Edmond into a free-fall that he mistakes for freedom, although he certainly now feels alive. Stumbling into a local bar, Edmond meets a man (Joe Mantegna ) who convinces him that sex is what he needs to solve his problems and points him in the right direction. To Edmond’s surprise, hookers are expensive, the pimp (Lionel Mark Smith) he encounters is violent, and the guy running a three-card monte game on the street is a cheat. Still, he wanders the streets, encountering big-city night crawlers, until finally he is robbed and beaten and left bewildered. “We live in a fog, we live in a dream,” he declares. Screeching racial hatred, Edmond finds a kind of peace in living in that moment.

Feeling freed, he goes home with a waitress, Glenna (Julia Stiles), but their riotous sex play leads to some very deep conversation. The two engage in a discussion about the meaning of race, death, life, and honesty. When the honesty topic is explored, Glenna refuses to engage, causing Edmond intense turmoil. He asks her, begs her, to rely on honesty, but instead pandemonium ensues. As Edmond spirals on towards personal disintegration, his racism and homophobia emerges – and he freely expresses it. “Every fear hides a wish,” he discovers.