Sophisticated people sneer at feel-good comedies and saccharine romances in which all loose ends are tied and everyone lives happily ever after. Life is nothing like that, we note, and we look to the arts for edification about the painful dilemmas of the human condition. -- Steven Pinker, in "How the Mind Works"
Some of us sophisticated people sneer at the saccharine romances, and love them all the same. That's why we (and I mean I) still go to films like "New Year's Eve." The feel-good and slick comedies feel good, but they also give us greater appreciation for movies like "The Wackness." (2008) Aside from its terrible title (and maybe aside from Mary-Kate Olsen's performance), "The Wackness" is good medicine for those who are sick of the formula films.
Set in New York in 1994 it's gritty and sad. The "wackness" signifies what's wrong with life, as opposed to the "dopeness" - the good side. The film has smart humor; humor that is not "hokey and gaggy," in the words of Olivia Thirlby, who plays Stephanie.
Luke Shapiro (Josh Peck) graduates from high school, even as his family is threatening to fall apart thanks to his father losing incredible amounts of money at work. He copes by hitting the streets, selling marijuana from an ice cream cart. He also trades dope for sessions with a messed-up shrink (Kingsley), the step-father of a girl in his class.
That girl, Stephanie, dabbles in Luke for the summer, while her cooler friends are out of town. She's having fun and he's falling in love. This is a more sophisticated example of the He's Out of Her League genre. Both parties have a veneer of cool, but his melts when he's around her. She tries to hold onto hers until it's too late. Once New York's sweaty summer approaches its finale, the shit hits the A/C for just about everyone concerned. There are plenty of Pinker's "painful dilemmas," with just a hint of edification. There is one interesting, subtle bit of pain as Kingsley's character sits by the riverside popping pills, with the Twin Towers in the background.
Peck makes a great streetwise naif, Kingsley is a creditable refined lunatic and Thirlby is not merely delightful to behold. She's a sharper, more dangerous version of the "Juno" role for which she's better known. "The Wackness" should've made a bigger impact on moviegoers.
But there's that title.

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