“Bitches, I like ’em brainless — guns, I like ’em stainless steel.”

Coming out of the mouth of the Notorious B.I.G., the line is uncut macho menace. But when it’s repeated in a scene in The Wackness by the man who played Gandhi, it inevitably takes on a different air: just how gangsta can Sir Ben Kingsley be?

This unexpected Biggie homage is one of many moments of empty braggadocio by the two damaged males in The Wackness. A frank and funny Sundance audience-award winner, it breaks the mould for contemporary teen flicks by avoiding both the pretty slickness of studio fare and the nihilism of Larry Clark’s brand of youthsploitation. Instead, the movie makes an unlikely hero out of Luke Shapiro (Josh Peck), an 18-year-old pot dealer and hip-hop head whose feelings of confusion and loneliness are partially assuaged by the words of Biggie Smalls (introduced to him by his Jamaican weed connection, played by Method Man).

His adult counterpart is Dr. Squires (Kingsley), a psychiatrist who trades couch time for Luke’s wares and is none too pleased when the troubled young man takes a shine to his stepdaughter Stephanie (Olivia Thirlby). Famke Janssen appears as Squires’ soon-to-be-ex-wife and, in another piece of stunt casting that turns out surprisingly well, Mary-Kate Olsen twirls around as a rich-girl hippie chick.

Set in New York in the summer of 1994, The Wackness strongly evokes the temper of its time. Signifiers include a graffiti tribute to the freshly dead Kurt Cobain, complaints about Mayor Giuliani’s campaign to clean up the city and a primo hip-hop soundtrack that gives major play to the Notorious B.I.G., the Wu-Tang Clan and A Tribe Called Quest. Though the film’s narrative and pacing can get logy, The Wackness is still exciting for the honesty with which it reflects the experience of a generation of moviegoers who aren’t used to seeing themselves on screen. (Levine established his knack for depicting teenage wastelands in All the Boys Love Mandy Lane, a horror flick that made a big splash at TIFF in 2006 but has been stuck in distribution limbo.)

As the 31-year-old director says in a recent interview, “It’s played pretty well across the board in the screenings I’ve been to, but with people who are either my age or just getting out of that high-school world now themselves, it resonates on a different level. There’s a passion for it as opposed to an appreciation.”

For one thing, it may connect with their passion for the sticky icky, though The Wackness portrays drug use without either demonizing or glorifying it. “I think the No. 1 statement the film makes is that drugs exist and that 18-year-olds often smoke weed,” he says. “It was certainly a part of my growing up. And within the themes of the movie — which are figuring out your coping mechanisms and figuring out how you’re going to proceed in life and be the person you want to be — it’s definitely resonant. But a lot of my job was policing the tone and making sure it doesn’t go too far in one direction.”

Nevertheless, the movie does accurately convey the murky feeling and hazy perspective that comes with having smoked far too much weed. The Wackness looks it, too, largely due to cinematographer Petra Korner’s insistence on keeping a smoke machine at the ready. Says Levine, “I was like, ‘C’mon, this is not a good idea, everyone’s coughing.’ Lucky for me, she was right. Once Kingsley started getting a little sick, we had to stop it but we’d already gone far enough in the right direction.”

That queasy tone is further complemented by the stark, death-obsessed sensibility of the hip-hop tracks on Luke’s headphones, especially Biggie’s afore-quoted “The What.”

“The Wu-Tang and Nas tracks are also pretty dark,” says Levine. “Each one of those albums has two or three tracks that sample a ’70s soul song and they’re much lighter and breezier but essentially the M.O. of each of those artists is dark storytelling. That’s very different from the Tribe Called Quest stuff, which is also in the movie. It was on the way out at that point but still very vibrant. That’s the strange juxtaposition of hip-hop: it’s this deeply confessional, raw thing on the one hand, and then it’s also about grabbing a beer, grabbing a girl and going dancing. Both contain lessons that are worth following.”

And despite the oft-repeated factoids about ’90s gangsta rap being principally consumed by white kids, it’s still unusual to see a movie that accurately portrays the music’s function in the lives of these fans. “Like punk and rock ’n’ roll before it, hip-hop was the music of rebellion when I was growing up,” says Levine. “And for Luke, it’s the framework by which he defines his emotions — I don’t think he ever really knew there were words for how he was feeling until he heard this music.”

Those words do include the ones quoted by Kingsley. Levine acknowledges that the sentiment could be construed as misogynistic, yet as he says, “the interesting thing is that this is the way these guys are hiding their vulnerability. They’re so at the mercy of their significant others that they need to pretend in order to maintain their masculinity. They pretend these women don’t mean anything, but the fact is, they mean everything.”