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. The newly-inaugurated mayor, Rudolph Giuliani, is only beginning to implement his anti-fun initiatives against ‘crimes’ like noisy portable radio, graffiti and public drunkenness.
Two people, however, are missing out on the excitement. Luke (Josh Peck) is a socially uncomfortable teenage pot dealer with no friends, issues with his parents, and a colossal lack of confidence with girls. He trades weed for sessions with his therapist, Dr. Squires (Sir Ben Kingsley), whose much-younger wife (Famke Janssen) is slipping away from him. Squires, a drug-addled shrink with a hairline retreating to the back of his neck and a state of mind slouching back to adolescence, is an unlikely role model, but the two of them forge a friendship based on a mutual need: getting laid.
The intergenerational duo set off on a crawl that takes them all over New York, where they encounter several of Luke’s business associates, including a Phish-following dreadlocked pixie (Mary Kate Olsen), a New Wave, keyboard-playing one-hit-wonder (Jane Adams), and Luke’s supplier (Method Man).
Luke has long had an aching crush on Dr. Squires’ way-out-of-his-league stepdaughter Stephanie (Olivia Thirlby) and is stunned at his good luck when she returns his affections. Luke’s innocent first love experience with Stephanie becomes a life lesson that sets him on the pathway towards adulthood. And when Squires breaks down, it is up to the younger man to throw the older one a lifeline.