A young male director making a coming-of-age movie about that transitional summer after high school seems to be as much of a rite of passage as the on-screen experiences—from the young men in rural 1950s Texas in The Last Picture Show, to American Graffiti’s small Californian town of ’62, to the suburbs in last year’s Superbad.

Just as those films reflect very specific years and places with the appropriate music, slang, and styles, so does writer/director Jonathan Levine’s The Wackness (though this is his second feature, his debut, All the Boys Love Mandy Lane, will be released later this year). Set in the hot and humid summer of 1994, street-level miscreants are just beginning to feel the impact of doing Giuliani Time. The increased police presence could cut into the plans of marijuana dealer Luke Shapiro (the charming, very Noo Yawk-inflected Josh Peck, who seems to be losing his pudgy, junior Jackie Gleason sitcom affectations from Nickelodeon’s Drake & Josh).

Trying to raise the cash to bail out his bickering, suddenly financially-strapped parents, Luke’s buying and selling takes him from his Manhattan home turf to “exotic places,” like Brooklyn and Queens, to meet a cross-section of stoners. From his philosophical supplier Percy (Method Man, just adequately playing a Rastafarian), he sells grass in the parks like a good humor man to the likes of neo-hippie Phish fan (Mary-Kate Olsen) and delivers to an ’80’s post-riot grrrl/barely one-hit wonder (Jane Adams).

Most creatively, Luke barters his product proportionately for therapy sessions with Dr. Jeffrey Squires, who just barely manages to give Luke practical advice on easing his depression before nodding after taking a hit from his large bong (or from the cabinet full of his own medications). As the long gray-haired shrink, Sir Ben Kingsley continues to bring to colorful life a recent string of unpredictably eccentric characters, like his unique criminals in John Dahl’s You Kill Me and Jonathan Glazer’s Sexy Beast. Dr. Squires insists what the lonely young man needs is a friend to talk to, and he, surprisingly, becomes that (and Luke becomes that for him as well as Dr. Squires becomes less a foolish foil for comic relief and more of a fully-realized character).

Of course, when the doc deeply inhales, he recommends that what Luke really needs is to get laid, a truism for this genre whatever the decade or locale where the young guy invariably and vividly daydreams about a girl who is a bit out of his league. The twist here—the object of his crush is the doc’s own stepdaughter, Stephanie (Olivia Thirlby). While her Upper East Side mother (Famke Janssen) is just an indistinct ice queen out of Gossip Girl, Thirlby (the best friend in Juno) imbues Stephanie with humanity, even when she’s toying with Luke or teaching him the facts of life. In period vernacular, she notes their divide: “I see the dopeness in everything, and you just see the wackness.”

The parallel yet intertwined travails of the older and younger generations set this film above the usual fare for this genre, with the tone changing from comic to romantic to poignant and back. The very illustrative period song selections reinforce these connections, with carefully chosen hip hop that samples resonant riffs from classic rock and R & B, such as A Tribe Called Quest’s use of Lou Reed’s “Walk on the Wild Side” in “Can I Kick It” and DJ Jazzy Jeff & the Fresh Prince’s “Summertime” reworking Kool & the Gang’s “Summer Madness.”