Fresh is an exercise in stupidity. The plot is a combination fairytale/suspense thriller, which makes it quite entertaining to watch (once the suspense starts), but the things it glamourises are what make it dumb.
Fresh (Sean Nelson) is the name of a kid who swears a lot, deals in cocaine, gets his friends killed, kills his own dog, plays chess brilliantly, and single-handedly metes out justice to the local gangs in his neighbourhood through sheer cunning. The movie is set so it is isomorphic to a game of chess: "the queen is expendable just like any other piece" is the advice his father (who's not allowed to see him) gives him as the boy is learning. This is evident in the treatment of girls in the movie. Fresh manipulates the tensions between rival gangs who deal in various drugs just like the pawns in a chess game so as to capture the "king". On the surface, one could imagine his goal is to clean the streets---but then the movie starts off with him dealing in cocaine. So the thing is that he initially makes choices so everything in the rest of the movie follows as a result of his initial choices.
Given that a person can get out of poor neighbourhoods by several honest methods, it is fascinating to see the method, laden with violence and lies, that Fresh uses. I say it is a fairytale because everything he does goes right for him. Reality sets in, however, when the girl he has a crush on is killed in a shooting in the playground. Perhaps using advice from his dad (which was given for a chess game), he manipulates his friend's death so it would be to his advantage. As in Natural Born Killers, the audience reaction is even more interesting---they laugh at the killings. It seems as though the Randian/Kantian philosophy of objectivism no longer has any meaning. That's a shame, because it should---there are basic (but non-absolute) tenets that we can live by, simply based on reason and productivity, neither of which seem to be highly valued in this movie.
The sole redeeming future of the film is Fresh's dad, who chastises him for using foul language. In the end, knowing that he has to be relocated and leave his father, Fresh cries a few tears for the actions he has committed. As if that will solve anything.