Its 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. This film centers upon one troubled high school student named Luke Shapiro (Josh Peck) a teenage pot dealer who forms a friendship with middle-aged psychiartrist Dr. Jeffrey Squires (Ben Kingsley). The two begin to explore both New York City and their own depressions. "The Wackness" is an offbeat tale of two lost souls stumbling towards maturity. Josh attends school with Dr. Shapiro's daughter Stephanie and develops a crush on her over the course of a long summer filled with many discoveries. Though Josh feels misunderstood and friendless, he has a friend in quirky customer Union (Mary-Kate Olsen)who catches the eye of Mr. Shapiro. Josh's parents meanwhile have problems of their own. But the biggest issue for all of them is how to stop seeing so much "wackness" in lives.