It's the summer of 1994 and Luke Shapiro (Josh Peck) has just graduated from high school. He is a quiet-spoken loner who sells dope in Manhattan to an eager clientele including two addicted women (Mary-Kate Olsen and Jane Adams). His supplier (Method Man) provides him with an endless supply of marijuana. Luke is fed up with his always squabbling parents who seem to him to be very immature. His father has blown a big business deal, and they face eviction from their apartment. This ominous event compels Luke to work harder so he can perhaps save the day for his family.
The adolescent drug dealer's best friend in the world is his therapist, Dr. Squires (Ben Kingsley), a middle-aged man with a marriage that is floundering. To pay for his sessions, Luke supplies him with dope. Squires is upset that such a young man is so sad, so he tells him to get laid. Luke has had very little experience with dating. He does develop a crush on Stephanie (Olivia Thirlby) who just happens to be Squires' step-daughter. When the therapist and his wife (Famke Janssen) take a trip to the Caribbean to try and revive their romantic relationship, Stephanie invites Luke to spend some time with her on Fire Island. She enjoys initiating sex and tutoring him in its ample pleasures. But he makes the mistake of falling in love with her, something she is not willing to deal with at this point in her life.
The Wackness is written and directed by Jonathan Levine, and it comes across as one of the oddest buddy movies in years. It makes perfect sense that the lonely adolescent boy and the bewildered therapist who's going through a midlife crisis would reach out for each other across the generations and offer some solace to each other. The film suggests that many men — of any age — are unable to handle heartbreak because they have so little experience with honestly dealing with their emotions. That is the true wackness at the core of this strange little drama.
Special DVD features include deleted scenes; a commentary with Josh Peck and director Jonathan Levine; Luke Shapiro's Dope Show; Keeping It Real: A Day in the Life of Jonathan Levine; and Time in a Bottle: behind-the-scenes of The Wackness.
