Writer-director Jonathan Levine shot The Wackness through the misty lens of nostalgia, as if applying a thin gel of wistful memory to the viewfinder. The slacker doofus protagonist, Luke Shapiro (Josh Peck), is graduating from his Manhattan high school and bound for the uncertain prospect of college. His family is coming apart under financial strain and he is now the unacknowledged breadwinner. Luke makes the rounds through the city pushing an ice cream cart filled to the lid with marijuana fresh off the boat from Jamaica.

  Unlike the pot dealers of an earlier generation, Luke’s outlaw status is bracketed by quotation marks. An ironic criminal, his diffidence verges on paralysis as he works the edges of the dope hip-hop scene because of what he sells, not because anyone thinks he’s cool. Luke looks at the world through a hazy scrim of depression, the narrowed eyes and horizon of a perennial pothead. He barters bud for talk therapy with his Deadhead psychiatrist, Dr. Squires (Ben Kingsley). Like his patient, Squires is profoundly unhappy and dependent on stimulants and depressants to make it through bedtime.

  The ray of sunshine in the druggy murk of Luke’s adolescent angst and Squires’ chronic mid-life crisis is the doctor’s fetching stepdaughter, Stephanie (Olivia Thirlby). Uninhibited and unpretentious, she regards her aging Baby Boomer step dad with tolerant, eye-rolling contempt. For his part, Luke erupts in anger at his ineffectual father, whom he dismisses as an overgrown child. Stephanie and Luke are products of parents who faked their way into adulthood. Squires keeps his medicine cabinet well stocked with lithium, valium and a dozen other prescriptions to dull his sense of failure, even as he proffers stale advice to Luke about cutting loose and experiencing the world that has crushed him.