The Basketball Diaries (1995)

A messy, energetic adaptation of Jim Carroll's 1963 underground memoir, in which the New York poet, author, and musician chronicled his teenage descent into heroin addiction. Late in The Basketball Diaries, when Carroll has fallen into the gutter, the audacious young actor Leonardo DiCaprio has a scene with Lorraine Bracco (as his mother) that can stand as one of the supreme harrowing moments in junkie-movie history. The rest of the time, though, DiCaprio never seems like a true street kid; he's too white-bread and suburban. The decision to transpose Carroll's story from the '60s to the present day gives the film a hazy, dissatisfying tone.