"The problem with you is that you have a shitty way of looking at things. I just look at the dopeness, but you just look at the wackness." Ouch. Tough talk coming from the girl of your dreams, but Stephanie The Wackness's been-there, banged-that uptown teenage heartbreaker turns out to be right on, in her glibly damaged way.
It's 1994, a moment simultaneously innocent and ominous, heady and paranoia-stoking: the year Kurt Cobain checks out of this temporal plane, while the Notorious B.I.G., OutKast, Nas, and assorted members of the Wu-Tang Clan check in with name-making first albums. New York City's new mayor, Rudolph Giuliani, is taking his crackdown on so-called quality-of-life crimes citywide, giving his police department more power to put the kibosh on graffiti, public beer drinking, and loud boom boxes. The threat of imminent arrest hangs, seldom spoken, over Luke Shapiro (Josh Peck), who's just graduated from high school and selling pot as the summer days melt away before his college years begin. Lonely and socially awkward, Luke either withdraws from reality, playing videogames and listening to rap, or stays at a safe remove, choosing a remote perch above the crowd at parties. The latter tactic comes in handy as he witnesses his parents' squabbling and increasing money troubles.
Luke's sole talent seems to be peddling weed from an ice cream cart as he roams the city. That, and making mixtapes, thanks to ideas caught from his supplier Percy (Method Man, who wittily introduces Luke to the Notorious B.I.G. by way of "The What," a Biggie and Method collabo). His only friend appears to be his therapist, Dr. Squires (Ben Kingsley), a gray-maned boomer who trades sessions for dime bags and is in dire need of some healing himself. Squires' stepdaughter Stephanie (Olivia Thirlby) is the hopelessly distant beacon of hope in Luke's firmament, so when the two are stuck in the city for one last summer before irrevocable collegiate change, Luke can't help but lose his cool.
Turns out it's the sweaty, sweltering season for everyone: a time to tell truths and strip away shopworn facades. Squires and Luke bond, roving way out of the office. The teen instructs the counselor in the ways of weed dealing, while amping up his business to save his family from eviction. The pair also look to get laid, Squires' prescription to all of Luke's ills. And the women do sail through, including Mary-Kate Olsen as Luke's jam bandy socialite client, who amazingly gets to second base with Squires, a half-mockable, half-empathetic character that Kingsley disappears into with sweaty, beady-eyed desperation.
Writer-director Jonathan Levine shows he learned a thing or two from a youth spent assisting NYC rhapsodist-anthropologist Paul Schrader. Painting this surprisingly gentle étude to an urban youth in sepia hues, he takes care to get the context right, from the vernacular built on "that's mad crazy" and "that's really dope" to a soundtrack laced with tunes like A Tribe Called Quest's "Can I Kick It?". That song's "Walk on the Wild Side" bassline conjures the gritty, narcotic lassitude of summer in the city while bridging the years between Squires and Luke.
Luke may not be as brainy and broken as Holden Caulfield or as mortality-fixated and mundane as Andrew Largeman of Garden State (2004), but Peck hits the right notes of cringe-inducing yet pungent realism required to turn this potential cipher into a full-fledged character. Especially when Luke dares to reach for dopeness and call Stephanie on a pay phone, and his "I love you" quickly turns into a defensive "OK, if you can't handle that, fuck it! Fuck you!" Alternately vulnerable, stumbling, and Teflon-clad, the kid will find his way through the urban jungle of his teens, one way or another.