The Basketball Diaries at 30: How Leonardo DiCaprio started – and abandoned – his ‘bad boy’ era

Leonardo DiCaprio in ‘The Basketball Diaries’ - (Island/Kobal/Shutterstock)

Leonardo DiCaprio may have been born in 1974, but he was made in the 1990s. Over the course of just a few years, DiCaprio went from total unknown to household name. Everyone remembers the Oscar-nominated turn as a learning-disabled child in What’s Eating Gilbert Grape; his role as Claire Danes’s star-cross’d paramour in the whizzy, revisionist Romeo + Juliet; and, of course, Titanic, that unsinkable behemoth of a romantic blockbuster. Fewer people, however, are likely to remember The Basketball Diaries, released 30 years ago today. But that film endures as a curious detour for the actor – the apex of DiCaprio’s hurriedly aborted “bad boy” era.

For much of the first half of The Basketball Diaries, DiCaprio’s insouciant athlete is almost a caricature of a teenage rebel: he fights; he smokes; he steals; he smoulders. An early scene sees him hunched over at the front of a classroom, receiving a robust rear-end paddling from a starchy Catholic schoolmaster. The bell rings. “Too bad, Father,” DiCaprio’s character smirks. “I was just starting to enjoy myself.” He and his delinquent cronies (James Madio, Patrick McGaw, and a just-out-of-Funky-Bunch Mark Wahlberg) then skive off school for the day; we watch as DiCaprio perches on the back of a moving bus, a cigarette dangling from his mouth.