It's the summer of 1994, and the streets of New York are pulsing with hip-hop and wafting with the sweet aroma of marijuana -- but change is in the air. The newly-inaugurated mayor, Rudy Giuliani, is beginning to implement his anti-fun initiatives against "crimes" like noisy portable radios, graffiti and public drunkenness. Set against this backdrop, Luke Shapiro (Josh Peck) spends his last summer before college selling dope throughout New York City, trading it with his shrink (Ben Kingsley) for therapy, while crushing on his step daughter (Olivia Thirlby).