Gus Van Sant’s dreamy, drifty, deadpan second feature—an addiction drama based on James Fogle’s autobiographical novel—captures the zonked-out textures and almost surreal absurdity of a life lived fix to fix. Swinging between dope-fueled disconnection and edgy paranoia, Matt Dillon plays the leader of a ragtag crew (also featuring Kelly Lynch, Heather Graham, and James Le Gros) that robs pharmacies for pills, coasting across the 1970s Pacific Northwest while trying to outrun sobriety and fate. With a brilliant supporting turn from counterculture high priest William S. Burroughs and a lyrical feeling for the streetscapes of Van Sant’s hometown of Portland, Oregon, Drugstore Cowboy cemented the director’s status as a preeminent poet of outsiderhood.

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