DiCaprio, now 51, has built a career many of his peers would envy. In that first film, 1993’s This Boy’s Life, adapted from Tobias Wolff’s memoir, he played young Toby, who’s nearly broken by the casual cruelty of De Niro’s character, a nightmare stepdad who lives by a code of hothead masculinity. At the time, virtually no one who saw this performance could believe this kid, his juvenile-delinquent swagger tempered by quizzical boyishness—he defined that fuzzy, confusing space between almost-a-man and still-just-a-kid so purely that you felt you were suffering through it yourself. Hollywood knew what it had: DiCaprio was offered what would have been life-changing money—certainly for a kid who’d been brought up modestly, as he had, often in rough L.A. neighborhoods—to appear in the Disney comedy Hocus Pocus; instead, he played a mentally impaired teenager in Lasse Hallstrom’s ardently unsentimental independent coming-of-age drama What’s Eating Gilbert Grape.