"You know who I hate? Faggots. Because they hate women." When Glenna (Julia Stiles) says this, it's a casual admission; something tossed off in the down moments of a one-night stand. It's a confession to a near total stranger that presumably won't cause any ripples in her real life, or ever be mentioned again. But Edmond (William H. Macy) is way ahead of her. Before meeting Glenna tonight, he knocked the teeth of a black man all over an alley in Times Square, and considered it a victory not just for himself but for what he views as the long-suffering white race. What luck, that he's found a kindred spirit he can tell his story to, detail by detail! Edmond is David Mamet's contribution to that strange film genre that dates back to John Ford's The Searchers, in which a lonely anti-hero's expectations of how things should be racially-wise, sexual propriety-wise, and otherwise-wise, must be adhered to by the rest of the world, lest he go completely schizoid.

Despite the considerable violence Edmond eventually racks up, Mamet's motormouthed version of Travis Bickle ends up coming off more like the world's most annoying bar patron than someone truly menacing. His pathos is inherently comedic, even if the filmmakers don't want it to be. His bete noire, we find out, isn't really blacks or women or city life, but high prices! Repeatedly thwarted in his attempt to find a low-priced call girl, Edmond at one point becomes enraged when a peep-show stripper is unable to make change for ten dollars from behind her glass window. "Give me the ten dollars! Give me the ten dollars!" Edmond yells, exasperated at how he ended up at such a moment in his life. The arguing of these two characters is so absurd that it almost saves the rest of the film, which is plodding, labored, and ultimately too theatrically-grounded for its own good.

Thanks to Mamet's well-earned reputation, director Stuart Gordon was able to stock his film not only with Mamet regulars like Joe Mantegna and Julia Stiles, but also with a starlet for each of several prostitute roles in the film. Denise Richards, Mena Suvari and Bai Ling all make the most of their one scene apiece, but their presence begs the question -- what universe are we supposed to be in, where easily accessible Manhattan prostitutes look like these women? Would the Edmonds of the world really be so forlorn if this was the norm? Stiles' lonely waitress character is the only one who seems remotely earth-bound in the looks department. She's not sure whether to be flattered or nervous when, after embarking on her one-night stand with Edmond, he begins to express a deep interest in who she is as a real person, deep within. He expounds on the fact that she is a "working woman" who deserves respect. "You're a waitress -- say it. Say 'I am a waitress'" he begs her, trying to give rise to some amorphous Marxist instinct that he believes she must possess. When she tires of playing along, things go downhill quickly. Director Gordon handles these scenes adequately, but his experience as a horror director is too evident. There are a few moments when he makes Edmond feel like a slasher film that just happens to have a low body count.

These uneven stylistic choices are one problem. The uneasy totter between comedy and violence is another. Yet another is that the film is heavily dated. As adapted by Mamet from his own play, Edmond screams "Manhattan Circa 1985" so loud that I was almost expecting to hear the theme music from the TV show Night Court. Times Square is a sewer, not yet a shopping mall. The characters are obsessed with a black-white racial paradigm that also seems now to be firmly anchored to the late 20th century. The threat of subway violence is highlighted. I could go on. Why did Mamet choose to keep his material tethered to a certain time and place, which so clearly saps its relevance? And what's with the title character's full name, Edmond Burke -- is it supposed to be a direct dig at devotees of the 18th century conservative philosopher who wept over the death of Marie Antoinette? Having never seen the original Mamet play, I have no idea. There's undoubtedly a bevy of material out there that would provide the answer for this, but since I'm too lazy to do my research, I'll assume the answer is yes.

There's a new generation of playwrights like Martin McDonagh who are deliberately trying to move theater away from its over-talkativeness and transform it into a more cinematic experience that is amenable to traditional movie genres. Mamet is not of that ilk, however. The best adaptations of his work to the silver screen are the ones where the director is fully in control and is able to streamline those classic Mamet dialogue chunks into the flow of an engaging story. I'm thinking in particular of James Foley's work on Glengarry Glen Ross. Even though the screenplay for Glengarry must have weighed five pounds, there's never a sense that we are at the mercy of a writer working without a net. Everything feels anchored to reality. With Edmond, on the other hand, no one could ever suspect that they are watching anything other than a filmed version of a play. This is especially true in the third act, which almost leaves orbit with its Samuel Beckett-like ruminations on life, love, God, the universe, and everything in between. The last twenty minutes of this film are so completely unrelated to the reality of how people talk that it feels like the writer is mocking the audience.