The operative word in Drugstore Cowboy is "drug". Matt Dillon plays the leader of a group of dopeheads who wander around the country robbing pharmacies to feed their habits. Dillon 's chums include doltish James Le Gros and teen-age junkie Heather Graham ; also along for the ride is Dillon 's wife Kelly Lynch . Their nemesis is cop James Remar , whom Dillon takes perverse delight in humiliating. When one of the young addicts dies of an overdose, it promps Dillon to try to go straight, a task complicated by wife Lynch 's determination to stay high and by the corrupting presence of an ex-priest, played by Naked Lunch author William Burroughs . Drugstore Cowboy was director Gus Van Sant 's breakthrough picture. — Hal Erickson