The Wackness (2008), R

Ben Kingsley and Josh Peck in The Wackness. (Photo: Sony Pictures Classics)

Starring: Josh Peck, Ben Kingsley, Famke Janssen

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 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, whose much-younger wife 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, a New Wave, keyboard-playing one-hit-wonder, and Luke’s supplier. Luke has long had an aching crush on Dr. Squires' way-out-of-his league stepdaughter, Stephanie, 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.