The hyper-nostalgia and perpetual adolescence of the kids of Generation Y has been discussed ad nauseam by the sanctimonious Baby Boomers who spawned them. At the risk of banal psychologizing and blatant oversimplification, it's not hard to see why Generation Y has a preference for the past. If polls are to be believed, this is the first American generation to believe the best times are behind it. Another thing the latest generation notices, besides its doomed future, is how miserable the Boomers, with all their "work on themselves," have managed to become. Which also explains the young's ubiquitous scorn for therapists.
The funny and touching coming-of-age dramatic comedy by writer/director Jonathan Levine, The Wackness, draws on both of these wide truths about Generation Y. Set in New York during the summer of 1994, The Wackness overflows with nostalgia for the period as it explores the relationship between a solemn 17-year-old, Luke (Josh Peck), and his psychiatrist, Dr. Squires (Ben Kingsley).

Luke is a sweet, hip-hop-loving virgin who sports shell toes and, usually, headphones. For money he sells weed out of an ice cream cart and when he's high—which is most of the time—he drifts into fantasies of scantily clad Fly Girls swinging from subway poles. When he arrives at Squires' office he promptly announces that he is "mad depressed, yo."

To which Squires, apparently from the Emotionally Young-ian School of Psychology, suggests a prostitute. Such sage advice from Squires isn't surprising once you've seen him at work. He trades Luke sessions for quarter ounces of weed (or, if a session is cut short, dime bags) and, as he hears the boy's troubles, Squires draws from a foot-tall bong and exhales the spent vapors through a paper towel tube affixed with a dryer sheet. Those who have tried this will laugh (and recall that it does nearly nothing to eliminate odor).

Luke takes the doctor up on his advice about getting laid, although, to Squires' dismay, Luke's crush is on Stephanie, the psychiatrist's stepdaughter. Stephanie—bored as much as anything—schools Luke in the ways of love and, as Luke reaches orgasm, he cries out "word!," and promptly develops "mad love" for his newfound "shorty."

The story progresses from there, balancing irony and authenticity and navigating thematic territory somewhere in the vicinity of Before Sunrise, Dazed and Confused and Wonder Boys.

Great details, such as a cameo role by Mary-Kate Olsen as a ditzy, dreadlocked Deadhead, more than make up for The Wackness' slightly thin drama. But if your first love happened during the time when Tribe and De La's sounds were giving way to those of Biggie and The Wu, when OJ was in a slow speed pursuit and Forrest Gump was the biggest film of the year, how can you say no, son?

The Wackness
Written and directed by Jonathan Levine
With Josh Peck, Ben Kingsley, Olivia Thirlby, Famke Janssen, Method Man and Mary-Kate Olsen
UA DeVargas, 95 min., R