There are many moments in Gus Van Sant’s Paranoid Park where you just don’t know what is going to happen next. Alex (fresh-faced Gabe Nevins, who the director recruited through MySpace stunt casting) has some sort of secret that he isn’t telling people. He’s a smart, good kid, but it feels like he is getting away with something big.

A Portland homicide detective drags him out of class to gently interrogate him about the recent death of a security guard, who was run over by a train near a dangerous skateboarders hang-out called “Paranoid Park”. This is a place where all of the kids whose parents don’t care go. They’re skaters, druggies, and castaways. They built it themselves. They have claimed it as their own have created an urban legend out of the place. “No one’s ever really ready for Paranoid Park”, says one boy to the cop).

The way the film unfolds is mysterious, and watchable. Van Sant tells the small story with striking images, and a slight flashback structure that never feels overly slick or un-organic. You might wonder, from the loving shots of pretty little skater boys in their boxers or in the shower if you are dealing with a director who is just nostalgic and reverent with his subjects or if he is just a dirty old man. Thankfully, it is the former. Don’t mistake the up-close-and-personal shots of the boys’ faces and bodies for anything other than a master approaching his subjects with loving care for detail and mood.

More honesty is folded into the mood by allowing the actors to be completely naturalistic (other than the screeching Taylor Momsen as Alex’s girlfriend). There is a shot of Alex, borrowing his mother’s car to go to the park to skate, alone, driving and listening to loud music, that is so reminiscent of that period in one’s life where being alone driving around, having your freedom, and doing what you want within reason is intoxicating and entertaining enough. It’s a brief, sweet scene, and the actor lets it happen unforced.

What could have been just another bogus, preachy after school special (adapted from Blake Nelson’s novel) has found a champion with the visually modern-thinking Van Sant and his new partner in crime, the masterful cameraman Christopher Doyle—who has shot for, among other projects, Wong Kar Wai’s spectacular In the Mood for Love. The marriage of photography and direction is one of the most important elements in personal filmmaking like Paranoid Park; without the marvelous mix of Super 8 (to mimic skate videos), and luxuriant 35 mm footage, the film would have just been another low budget, predictable, straight-to-video for the teens outing. The shots that build tension, the lighting, and even the way rustling grass is shot by Doyle gives the proceedings a more meditative mood, rather than chaotic. There is a very Zen quality to the look of the film.

Van Sant is no stranger to turning ordinary stories into extraordinary films: My Own Private Idaho, Drugstore Cowboy, and To Die For all blossomed in the director’s hands. Along with the Cannes triumph Elephant (which Paranoid Park will unjustly get compared to), the Portland native shows that he has the market cornered on telling the stories of teenagers in the most realistic way of any working director. He has a feel for youth counter culture that other directors just miss completely.

Like in Vadim Perelman’s In Bloom, being at this peculiar in between age is seen by Van Sant as a time of great reflection and great exploration of one’s own conscious. The scene where Alex wrestles with his own questions as he leaves the park is a marvel of sound editing (as is the rest of the ambient mixing used throughout). He is trying to rationalize this crime in his own mind, deciding for himself what is right and what is wrong. It seems like this could be the first time he has been left to his own devices like this, no mom, no dad to bail him out.

Both films employ successful flashback structures, and both are similarly informed by the traumatic effects of violence (albeit accidental), on someone so essentially innocent (and In Bloom does owe a lot to Elephant. While calling these films and their themes “coming of age” is probably not appropriate—as that arouses connotations of bad memories of teen flicks past, it is safe to say that Van Sant is concerned with portraying the developing moral compass of a jaded youth with a heartfelt sincerity and a steady hand.