5. Drugstore Cowboy
This 1989 film starred Matt Dillon as Bob, a drug addict whose habit led himself, his girlfriend and another couple to rob pharmacies. Tragedy hits the group when one of their friends overdoses, at which point Bob decides to get clean and stop using. While he is somewhat successful in leaving his former life, as a former friend begins to stalk him, and eventually robs and shoots him in his apartment while searching for a fix.
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The story is a (somewhat) true to life autobiography of James Fogle, a career criminal from Wisconsin who wrote while serving jail time after a series of crimes in his youth.
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