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

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.
The film veers into darker territory, as DiCaprio's character becomes addicted to heroin and lives on the streets. It's all in all something of a mixed bag: unevenly paced, self-consciously edgy, and lacquered with histrionic cliché. Put this together with the film's meagre commercial performance and it's unsurprising that The Basketball Diaries islittle more than a footnote in the scheme of DiCaprio's career. (It may in fact be best known for a dream sequence depicting a school shooting, which later prompted lawsuits in the wake of two real-life shootings.) But it's noteworthy just how rare it was to see DiCaprio explore a character this smarmy and obnoxious.
Not too long after The Basketball Diaries was released, DiCaprio signed on to Woody Allen's Celebrity – another instance of his apple-cheeked persona breaking bad. (Back in the 1990s, Allen films were of course a hugely attractive proposition for any actor, not fraught with ignominy as they are today.) The glossy black-and-white comedy cast Kenneth Branagh as an archetypical Allen nebbish, and DiCaprio, in a supporting role, as a bratty and mercurial A-lister. By that point, DiCaprio and his social circle (a group of young, mostly male celebs including Tobey Maguire, future Entourage star Kevin Connolly, and the magician David Blaine) were the subject of significant tabloid attention. Celebrity 's metatextual overtones were hard to miss – hot young superstar DiCaprio playing hot young superstar Brandon Darrow – even if the extremity of the character's hotel-room-trashing behaviour was a fabrication of the film.
The late 1990s also saw a protracted dispute over Don's Plum, a bizarre and unpleasant indie film starring DiCaprio, Maguire, and other members of their friend group (who styled themselves, if tabloid reports were to be believed, as the 'p***y posse'). It's perhaps the grimmest iteration of DiCaprio's edgelord phase; one moment sees DiCaprio's character yell at Amber Benson that he will 'f***ing throw a bottle' at her face, calling her a 'goddamn wh***.' The film was panned by critics, but its release was infamously blocked, with its actors claiming to have participated in the understanding that they were making a short film, not a feature.
There would be other roles for DiCaprio that loosely fit the 'bad boy' remit – his thrill-seeking globetrotter in The Beach had elements of this, certainly – but it never played to his strengths. (He was nearly cast as the lead in the 2000 adaptation of American Psycho – a prospect that would have really put his capacity for nastiness through its paces.) In the Nineties, he was defined by a sort of boyish, approachable-but-not-too-earthy confidence; it's what makes his Romeo, and the plucky Jack in Titanic, such winning romantic leads. He seems too much the pretty boy to be a natural fit for malignity, and it's no surprise that the 2000s saw him largely pivot back to more likeable leading-man roles.
From the very offset, DiCaprio has never really been an actor with a rigid persona. It's significant that his breakthrough – playing the learning-disabled Arnie in What's Eating Gilbert Grape – was a distinct, mannered performance, more befitting a 'character actor' than a movie star. As the 1990s progressed, and he became a little more consistent in his choices, his forays into antiheroism can perhaps be seen as an effort to resist Hollywood's natural pigeonholing. Later in his career, he would branch out into scumbaggery with greater success, in projects such as Django Unchained and The Wolf of Wall Street.
Here's a coincidence for you: The Basketball Diaries is in fact one of two entirely separate projects in which DiCaprio is spanked with a paddle. The second is 2023's Killers of the Flower Moon, wherein DiCaprio's character – a spineless, selfish and dimwitted poisoner – is given a paddlin' by his uncle (Robert DeNiro) in a masonic ritual.
The difference between these two scenes is actually rather illuminating. In The Basketball Diaries, we watch DiCaprio's character bear the punishment with a kind of defiant cheek we are supposed to find charming. In Killers of the Flower Moon, it's a silly and embarrassing spectacle for all involved. Watch DiCaprio in any recent film, and it's noteworthy just how uninterested he is in preserving his own dignity. It's a shamelessness that he hadn't yet mastered back in the days of The Basketball Diaries, or even Celebrity. In something like The Basketball Diaries, we see the seeds of the performer that DiCaprio would one day become. He just had to wait a couple of decades for those seeds to sprout.

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