Plot
Urbania follows Charlie through a sleepless night. After an unsuccessful bout of masturbation to the sound of his upstairs neighbors having sex, he prowls the streets looking for a man he saw several months earlier. The implication is that he has had a one night stand with the man, cheating on his boyfriend Chris. This is reinforced by several phone calls Charlie places, leaving messages on Chris's answering machine. As he is walking, he has momentary flashes akin to hallucinations or waking dreams: a man's mouth; a bottle breaking; a man with a blood-stained shirt.
After a series of encounters (with his upstairs neighbors, whom he tells about his masturbatory activities; and with a potential sex partner), he meets the man he is looking for. His name is Dean and it makes no sense either that he would have sex with Charlie or that Charlie would have sex with him. Dean is unabashedly racist, sexist and homophobic. Nevertheless, Charlie, pretending to be straight, buys Dean drinks and smokes a joint with him. Dean takes Charlie to a gay cruising area looking for victims, but Charlie is able to warn away the intended target. Dean is now almost incapacitated by alcohol and drugs and Charlie gets him into Dean's car and drives him to a secluded marshy area.
As had been implied by Charlie's flashbacks, Dean and two of his buddies, several months earlier, had attacked Charlie and raped and murdered Chris in an apparent hate crime. Charlie's purpose is finally revealed: he wants revenge.
In a dreamlike conversation with Chris, Charlie relates what happened at the marshland. He pulled a knife on Dean and told him why he was there. Dean did not remember him. Charlie forced Dean to drop his pants and was disgusted to see Dean had an erection. Charlie forced Dean to kneel and fellate the knife blade. Suddenly, Dean collapsed with an epileptic seizure. Charlie slit his throat.
Chris challenges Charlie, not believing that he killed Dean. Charlie admits that he wanted to but could not. Instead, he drove off in Dean's car, abandoning him in the marsh.
Charlie stands up from where he has been kneeling, at a makeshift memorial near where Chris was killed. He walks home and has one more hallucinatory flash. He sees himself on the street, cradling a dying Chris. He kisses Chris goodbye and passes by him. When he turns back, Chris is gone. Charlie makes it home and, finally, is able to sleep.
Charlie presents aspects of his story in the form of urban legends. The film references a number of urban legends, both by having characters describe them as they are depicted and by presenting random people experiencing them.
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