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As a native Oregonian, I have a soft spot for Van Sant, who's lived and worked in Portland for much of his professional life, though I admit to disliking his recent output. Still, his best films represent some of the most worthwhile American filmmaking of the last few decades, independent and otherwise. You can catch my five favorite after the jump.
5. Paranoid Park (2007) Probably his last truly great film, though Milk, albeit formally inert, is certainly commendable for its laudatory depiction of Harvey Milk. Dreamlike and somber, the film strikes me as one Van Sant's most instinctual, governed less by matters of narrative and continuity and more by the emotional arcs of his protagonist.
4. To Die For (1995) The most outwardly comedic film of Van Sant's career so far, and a fine one at that. He gets a tremendous amount of mileage out of Buck Henry's script, reveling in its tabloid-trash milieu as much as he satirizes it. Appropriately dark, the film ends with a delicious visual metaphor that brings new meaning to the phrase "dancing on your grave."
3. Mala Noche (1985) A vital document of a pre-Portlandia Portland counterculture, shot on black-and-white 16mm film that highlights the city's gray skies, wet streets, and gloomy atmosphere. The cast is filled with local eccentrics and nonactors, further legitimizing the film's faithful depiction of Portland's Skid Row, an actual neighborhood (and not just a state of being) inhabited by starving artists and armchair intellectuals that essentially birthed the hipster culture that's given the city its reputation.
2. Drugstore Cowboy (1989) Van Sant's survey of the American ideal, a spiritual successor to the likes of Badlands and Easy Rider in its treatment of criminal characters who don't strive to do bad yet seem unable to avoid trouble. An atmosphere of dread and disillusion pervades the film, but there's also a sense of playfulness, thanks to the idiosyncratic characterization and rich location details. And, of course, there's the amazing cameo from William S. Burroughs, whose distinct style no doubt helped shape the film's tone.
1. Elephant (2003) For various reasons, I have a tremendous amount of sentimental fondness in this film, but aside from my personal affinities, I find this lyrical drama to be the most rewarding and formally proficient of Van Sant's work. Its visual rhythms and nonlinear narrative processions elicit a hypnotic tone that nevertheless resonates on a sociopolitical level. It also features some of the best work by the late cinematographer Harris Savides, with whom Van Sant collaborated on numerous projects.