Leonardo DiCaprio on the set of The Basketball Diaries. Photograph by New Line Cinemas via Getty Images.

Leonardo DiCaprio’s Rooftop Jerkoff: The Most Important Self-Sex Act in Cinema

It isn’t embarrassing. It’s almost romantic.

by Trey Taylor
|
Dec 27 2018, 9:19pm

Leonardo DiCaprio on the set of The Basketball Diaries. Photograph by New Line Cinemas via Getty Images.

“Time sure flies when you’re young and jerkin’ off,” Leonardo DiCaprio muses in the famous rooftop masturbation scene in The Basketball Diaries, based on Jim Carroll’s 1978 memoir of the same name. Sandwiched in between harrowing depictions of DiCaprio's smacked-up character Jim Carroll experimenting with hard drugs, it's a bit weird that this 46-second episode got all the attention it did. After all, the film is about a high school Basketball Jones who spirals out of control and resorts to shooting up heroin, not a kid who can't get laid.

But as for the near-instantaneous spot of self-service? That gets mentioned in reviews of the film from Rolling Stone (“The film misses Carroll’s poetic eroticism”) to Roger Ebert (“the movie heroically declines to score this scene with ‘Up on the Roof’”). It's forewarned in conservative kid-friendly ratings sites like Catholic Boy and Kids In Mind. It's a moment we've culturally deemed worthy of guiltily replaying in our minds, long before we knew what the Pussy Posse was really up to between takes.

DiCaprio's quickie is arguably one of the best masturbation scenes in cinematic history. We're judging on sheer poetics here: It's lyrical, introductory, inquisitive. Narrated with 21-year-old Leonardo's disintegrating ASMR whisper: “I don’t think of anything while I’m doing the actual tugging. Least of all the heavy sex fantasies I have to resort to indoors,” he says, supine on the tarred roof of a brownstone, arm cranking like a pumpjack, “Just my own naked self and the stars breathing down, and it’s beautiful.” Aimed at just the kind of audience the film was bound to attract when it initially debuted. It flung open the doors for frank discussions of self-pleasure.

Sex Geekdom's Gareth Durrant went long on how The Basketball Diaries showed him the ropes at the age of 11. “I was Helen Keller and seeing Leonardo DiCaprio masturbate on that New York City rooftop was my water pump,” he writes. Add to the Rooftop Rub Club stand-up comic Moshe Kasher, who wrote in his autobiography Kasher in the Rye that Jim Carroll's cult 1978 book spelled out that touching oneself didn't simply mean putting “your hand down your pants while watching TV, à la Al Bundy.” There was a lot more to it.

So why was this scene in particular so important to introducing this crucial, yet still almost painfully embarrassing-to-discuss sexual act into the cultural canon? “For many people (and certainly those coming of age prior to the internet) it was their first exposure to masturbation, and it’s certainly the most comprehensive educator given the paucity of information available in more formal education sources,” says Lauren Rosewarne, senior lecturer at the University of Melbourne and author of Masturbation in Pop Culture: Screen, Society, Self.

Rosewarne continues, “Scenes that focus on pleasure and present masturbation as separate from humiliation, desperation and substitution help to shape it in the imagination as a viable sexual option and not simply the refuge of the unfuckable.”

DiCaprio spoke about “feelin’ myself” long before Nicki, and it isn't embarrassing; it's almost romantic. The early ‘90s poster boy was preaching about it in the media, and teaching it on-screen. It's human nature. More than spurring giggles from its audience, it kickstarted discussions around such a taboo subject, and solidified this as the lasting legacy of a film that told us that self-loving isn't anything to be ashamed of.

Now, in the words of Ariana Grande on the smash hit “Better Off”: “Let's put them topics to bed and go fuck on the roof, just to say that we did it.”