Jonathan Levine's nostalgic reverie recreates a more innocent New York. In 1994, the Twin Towers watch over Manhattan, and Rudolph Giuliani reigns as mayor--not a bestselling author or presidential candidate. Recent high school grad Luke Shapiro (sleepy-eyed Josh Peck, Drake and Josh) plies the kind of trade Giuliani seeks to discourage: dope dealing. Otherwise, though, Luke's not such a bad kid. He sees a therapist, the pot-smoking Dr. Squires (Sir Ben Kingsley), and nurses a crush on the doctor's flirtatious stepdaughter, Stephanie (Juno's Olivia Thirlby). Hip-hop fills the air, and Luke spends his days grooving to Nas, the Notorious B.I.G., and A Tribe Called Quest, while selling cannabis out of an ice-cream cart (Wu-Tang rapper Method Man plays his Rasta supplier). As the summer heats up, Luke and Stephanie grow closer, while Squires and his wife, Kristin (Famke Janssen), drift apart. Meanwhile, Luke's family faces eviction if his father's fortunes don't improve, and he finds himself torn between the hot girl, the bummed-out shrink, and a job that could land him in the clink for a good long time--or save the Shapiros from moving to New Jersey. Though Levine (All the Boys Love Mandy Lane) doesn't judge his law-breaking protagonist, he does suggest that love can make a smart guy lose his head just as easily as lust--and even a trained psychiatrist can't always tell the difference. With Mary-Kate Olsen (Weeds) and Jane Adams (Happiness) as the spaciest of Luke's spacey customers.