In the sweltering summer of 1994, Rudy Giuliani is scouring New York City within an inch of its life, hip-hop is permeating white youth culture, and a pot-dealing loser kid, Luke Shapiro, is trying to figure out how to solve his parents’ insolvency, beat depression, and get laid before pushing off to college. Luckily he’s got a nifty deal with a psychiatrist, Dr. Squires, who trades him therapy sessions for weed. It happens that the oddball doctor’s marriage is crumbling, so the two—one in late adolescence, the other in late middle-age—embark on messy passages into new life stages. As Luke falls for a classmate who just happens to be Squires’s daughter, the summer heats up, and he follows doctor’s orders, learning to coexist with pain and make it part of him, rather than let it become his downfall.
The Wackness plays like the luscious rush of first love, discovering great new music, meeting amazing personalities who impart the meaning of life, and realizing what you’re made of. Perfectly capturing the textures of 1990s Manhattan and the zeitgeist of worldly, yet emotionally unformed, private-school students forced to parent their parents, director Jonathan Levine conveys a whimsy, too—buoyed by the dazzlingly funny Ben Kingsley and unexpected stylistic flourishes—that gives the film’s insights and idiosyncrasies big, glorious, flapping wings.