In Gus Van Sant's feature-length directorial debut, Drugstore Cowboy (1989), Matt Dillon plays Bob, the natural leader of a group of four drug-addicted felons on the lam in the 1970s. Around and around they go, sticking up hospital and pharmacies across the Pacific Northwest, often making out with a considerable quantity of high-power painkillers to feed their habit. Not until a terribly tragedy hits the group does Bob try to clean up his act—which proves even more difficult that he'd expected it to be.
An autobiographical novel by James Fogle (the real-life Bob), which served as inspiration for the film before it was even published, was released the year following the film's release, by which time Fogle had been released from prison. Old habits die hard, though: in March 2011 Fogle was arrested for the robbery of a Seattle pharmacy and was sentenced to 15 years and nine months in prison. So long, Cowboy. [Netflix]