Janis Ian, Lindsay Weir, And Other All-Time Favourite Teenage Misfits

The Way Way Back is a movie where an awkward, misfit teen learns to deal with the world around him. It’s a story we’ve seen played out hundreds of times before, but the film’s so achingly well-made and acted, it makes you forget that the tale you’re seeing is a familiar one.

Liam James stars as Duncan, a withdrawn and hopelessly dorky kid who takes a summer job, befriends a louche, older gadabout played by Sam Rockwell, and learns to stick up for himself.

The film hit cinemas yesterday, so let’s use that as an excuse to look back at some of the greatest misfit teens in the history of film and television. With these awkward youngsters, Liam James’ Duncan is in very good company.

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Janis Ian – Mean Girls (2004)

Lindsay Lohan may have been the star of Mean Girls, but Lizzy Caplan gave the film’s real breakout performance. Her Janis Ian is the greatest – the cool, snarky friend you always wanted in high school. She and her ‘too gay to function’ sidekick Damian take their outsider status and wear it as a badge of pride, forming their very own army of two. Janis has the best comebacks, the best prom outfits and the evil-est schemes, but above all, she is loyal to the end.

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Veronica Sawyer – Heathers (1989)

Winona Ryder’s Veronica Sawyer is the queen of disaffected ‘80s teens. Fed up with life in her popular high school clique (which consists of her and three girls named Heather), she longs for an escape. She finds it in dashing bad boy J.D. (Christian Slater), who is every teen’s dream… until he turns out to be a homicidal maniac. “Dear diary,” she writes as she’s drawn into his murderous plan, “my teen angst bullshit has a body count.” Veronica Sawyer reigns.

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Shaun Brumder – Orange County (2002)

Every misfit teen dreams of escape, even if the thing they want to escape isn’t really that bad. Colin Hanks’ Shaun Brumder is the perfect example. He leads a privileged existence in a Southern California mansion, but amid the surfer dudes and trophy wives of his social circle, what he really wants is go to college and be a writer. Shaun’s dilemma is kind of ridiculous, but the movie is aware of this and plays it for laughs, which is what makes him so appealing. No offense to Seth Cohen, but Shaun Brumder is the original dork from The O.C.

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Lindsay Weir – Freaks And Geeks (1999 – 2000)

There are lots of ways to be a misfit, as Linda Cardellini’s Lindsay Weir discovers in the much-loved Freaks And Geeks. When the smart and gifted Weir has a teen angst attack, she is drawn away from her nerdy crowd towards the burnouts, essentially trading one group of high school outcasts for another. Throughout the series, she keeps a foot in both camps, while negotiating her own identity as a smart, independent youngster.

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Becca Moody – Californication (2007 – present)

Say what you want about Californication — the Showtime staple has become increasingly silly in recent years — but Hank (David Duchovny) and Becca Moody (Madeleine Martin) are one of the best dad-daughter pairings on TV. With her subtle snark and her uncommon insight, Becca essentially acts as her philandering dad’s moral compass. In the show’s early seasons, she often seems to take on the parent role for her dad. Becca puts up such a mature front that the people around her often forget she’s a kid, capable of messing up and getting hurt.

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Anna Stern – The O.C. (2003 – 2007)

I don’t mean to turn this list into a Seth Cohen-bashing, but for me, the first season of The O.C. was really all about Anna (Samaire Armstrong). A transfer student from Pittsburgh — that’s a thing, right? — Anna doesn’t fit in with the Newport Beach crowd. She prefers creating homemade comic books, channelling Rose from The Golden Girls and using big words like ‘anathema’. The dorky Anna skips town after Seth chooses Summer in their inevitable love triangle, but I always wonder how much cooler The O.C. would have been had she stuck around.

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Cameron Fry – Ferris Bueller’s Day Off (1986)

Everyone knows that, for all of Ferris’s own antics, Cameron (Alan Ruck) is the real star of Ferris Bueller’s Day Off. At the start of the movie, Cameron is so depressed and withdrawn that he’s borderline dysfunctional; over the course of his adventure with Ferris and Sloane, he comes out of his shell and even learns to lighten up. Though we never see his climactic confrontation with his overbearing dad, we’re pulling for him to stand up for himself.

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Patrick – The Perks Of Being A Wallflower (2012)

The Perks Of Being A Wallflower is about a trio of misfit suburban teens in the early ‘90s — some have called it the best movie John Hughes never made, and from the soundtrack to the warmly nostalgic tone, it’s easy to see why. Ezra Miller’s Patrick is the most compelling of the central trio, as a gay kid who is secretly dating his high school’s quarterback. He’s messy, imperfect and highly dramatic, but also one of the most relatable gay teens ever to make it on film.

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The Way Way Back is screening in cinemas nationally now.