Drugstore Cowboy (1989)
In one of his first real grown-up roles, Dillon earned raves as Bob, the fatherly leader of a quartet of junkie burglars, and the only one who makes a serious effort to go straight and get clean. A gritty and at times shockingly funny film, Drugstore Cowboy also put director Gus Van Sant (Good Will Hunting) on the map.
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