The Wackness | What We Did On Our Summer Holidays

Credit: Sony Pictures Classics

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Kirsty Asher

The summertime can evoke a very particular brand of nostalgia. Summer’s association with fleetingly impermanent leisure grants it a wistful quality. It can be an optimum time to create cultural moments, even if they aren’t seen as such at the time, and particularly when a certain summer predates a notably difficult or traumatic event. A good example of this was summer 2018, which UK Twitter has recently decided was the perfect summer for its heatwave, England’s moderate success at the World Cup, and a particularly good season of Love Island. With the tail end of Summer 2021 becoming a comparative washout, I turned my attention to the sun-soaked Manhattan streets of Jonathan Levine’s ode to summer nostalgia, his director-writer debut film, The Wackness (2008). 

The film is a coming-of-age story about hapless New York weed dealer Luke Shapiro (Josh Peck) as he tries to gain some life experience before starting college. ‘Life experience’ in this instance mostly refers to losing his virginity, ideally to Cool Girl Stephanie (Olivia Thirlby) who also happens to be the stepdaughter of local psychiatrist Jeff Squires (Ben Kingsley) who gives Luke therapy in exchange for dope.

Levine’s reimagining of ‘90s Manhattan is complemented by the astutely selected hip hop soundtrack. Shapiro’s loserish life is sent up in his introduction to the audience with Nas’ The World is Yours, and the overarching narrative of being friendzoned and left heartbroken is epitomised by Biz Markie’s (RIP King) anthem for the lovelorn, Just a Friend.  Graffiti tag font abounds in the title credits, and cinematographer Petra Korner reportedly used vintage Baltar lenses to pick up lens flares, giving the film its hazed lighting, like a cloud of nostalgia. Here, Biggie is still on the cusp of stardom. Rudy Giuliani is only just embarking on his draconian tenure as Mayor of New York City. 9/11 has yet to happen. The film spotlights a relatively stable moment in American history just prior to an enormous cultural and political shift, as the ‘90s itself has come to symbolise. 

In this sense, the film had the makings of a highly appealing nostalgia-fest. But while The Wackness won the Audience Award at Sundance 2008, where it premiered, it ended up getting lost in a summer which also saw the release of more prominent indies like Rachel Getting Married and Wendy and Lucy. But what is singular about The Wackness is its approach to cultural nostalgia, and how it manifests itself on a personal level compared to a collective one influenced by fashion trends, consumerism, and shifting demographics.    

The Wackness was made during a time when ‘90s nostalgia was not yet part of the zeitgeist. Levine conceded this in an interview with the festival circuit’s favourite bouffant, First Showing’s Alex Billington, following the film’s Sundance 2008 premiere. Harrison Ford’s return as Indiana Jones that year shows a clear hunger for the 1980s revivalism which was largely apparent in 2000s pop culture, in keeping with the popular history theory of collective nostalgia moving in 20 year pendulum cycles. In this sense, Levine wasn’t attempting to capitalise on an ongoing trend, but instead aimed to use the period setting to introduce young audiences to the cultural background of his own adolescence, and to do so enthusiastically. 

This is evident in Levine’s decision to use young performers known for their contribution to ‘00s pop culture. It was Peck’s feature debut following the end of the popular sitcom Drake and Josh (2004-2007), while Thirlby had starred in the 2000s touchstone coming-of-age film Juno (2007) the year before. Mary-Kate Olsen, also known for her significant contribution to ‘00s youth pop culture with her twin sister Ashley, cameos as an unsettling hippie flower child, who we have to endure watching ride Kingsley in a phonebox after a night out. Peck himself was hopeful that his appearance in the film would appeal to audience members who were young children in the ‘90s: “…the fans of [Drake & Josh] – for example, someone who was 12 years old when I was 15 – will have grown up with me. I’m 21, so they would be 18 now, and I think this movie is right in their wheelhouse.” 

The problem with this creative decision is that it becomes difficult to extricate these stars from their contemporary appeal. Consider Richard Linklater’s Dazed and Confused (1993), which, like The Wackness, was a low-budget reminiscence of youth that made limited impact upon first release. The ensemble cast were a group of relative unknowns for which the film was their first steps on the road to stardom, and as such the film built its cult status steadily as time went by and their careers bloomed. Matthew McConnaughey has traced a smooth trajectory from his breakout performance in Dazed to his Oscar acceptance speech through the immortalisation of his catchphrase “Alright, alright, alright.”. As Parker Posey’s first major film role it was the starting point in her trajectory to becoming the ‘90s indie queen. Josh Peck was looking to remain relevant following the end of Drake and Josh, and while the themes of this film (plus a sun-drenched shot of Peck’s barenekkid ass) give it something of an edge, the role still allowed him to play up a sweetly dopey persona that had one foot in the Nickelodeon grave. Meanwhile, Olsen was in semi-retirement from acting, and while Thirlby was certainly memorable in the sarky best friend role in Juno, she doesn’t quite have the magnetic leading lady appeal needed here for her role as love’s first heartbreak. 

Levine cited Superbad (2007) and Juno (2007) as recent popular youth films which he felt were exemplary, but the appeal of these films was that they were highly modern narratives which leaned on retro aesthetics to embellish the story, rather than induce nostalgia. Superbad used a funk & soul title sequence and soundtrack, and similarly Juno had kitschy thrift shop production design with a title sequence inspired by 1970s punk rock posters. With The Wackness, the aesthetics, particularly the costume design, never quite teetered into the realm of retro. Kingsley’s Dr Squires is rarely without his fedora hat, and what was 2008, if not the fedora persevering? With Olsen’s career turning to fashion design in 2004 and the twins’ cultivation of the ‘boho chic’ look in the mid-00s, playing a hippie with flowers in her hair did little to invoke ‘90s youth culture. Similarly, the film’s attempts to invoke nostalgia for dated technology failed to strike home. SNES consoles and mixtapes hardly felt outdated in a time when GameBoys were still in use. Nick and Norah’s Infinite Playlist (2008) which came out the same year, centres around two people who love making mix CDs. It’s hard for nostalgia to resonate if cultural references haven’t been given time to fall out of immediate relevance. 

Where history might well be kind to Levine’s film is the notion that it was an honest labour of love by a director who wanted to celebrate the past, regardless of whether it turned into a financial or cultural capital boon. As Thirlby’s character Steph eponymously puts it to Peck’s Shapiro during one of their meandering trysts, you’ve got to look for ‘the dopeness’ rather than ‘the wackness’ in life. The real wackness in this day and age is how fast fashion and media guzzles down the ‘90s aesthetic for profit and clout. Maybe Gen Z, or even Gen Alpha, will seek out The Wackness in the quest for an honest puff of the nostalgia cheeba.