The best teen movies based on classic literature

This week marks the 18th anniversary of the release of Cruel Intentions, one of the most provocative entries in the high school movie genre.

It is one of a spate of teen flicks made in the 90s and early 00s which borrow their storylines, characters and themes from works of literature and repurpose them for a young audience. In honour of Cruel Intentions coming of age, here’s a round-up of the smartest, sassiest high school films inspired by the classics.

Cruel Intentions
(Les Liaisons Dangereuses by Pierre Choderlos de Laclos)

In 1999, Sarah Michelle Gellar was America’s sweetheart; young viewers loved watching her dust bloodsuckers and crack wise as the cheerleader-turned-heroine in Buffy The Vampire Slayer. So when Gellar took the starring role of social schemer Kathryn Merteuil in a reimagined version of Dangerous Liaisons, it was a conscious step away from her usual image — and I’m not just talking about the dark hair. Kathryn is everything Buffy isn’t; she’s vain, manipulative, sexually aggressive, and highly vindictive. Which is to say, she is a joy to watch as she toys with the emotions and reputations of literally everybody else on screen.

The film’s success spawned a swiftly made, straight-to-video prequel (starring a young Amy Adams, no less) and even a stage musical. Last year, news broke that Gellar might be reprising the role of Kathryn in a new TV series. Considering the comeuppance Kathryn received at the end of the film, a show exploring the character’s later life as an embittered adult sounds deliciously dark.

(Emma by Jane Austen)

We’ve all got that one friend who can’t help getting involved in other people’s business. And in 1995, that friend was Cher Horowitz, matchmaker and fashion icon who takes it upon herself to give the new girl a makeover while also playing Cupid to her teachers. And while sure, Cher is a privileged rich girl meddling in the lives of others, she is the polar opposite of Cruel Intentions’ Kathryn. She’s a font of optimism and positive energy, seeking only to make other people happier — and if it gets her better grades along the way, so be it.

10 Things I Hate About You
(The Taming of the Shrew by William Shakespeare)

10 Things takes the convoluted marriage plot of Shakespeare’s comedy and thoroughly updates it. Bianca is a social butterfly and every boy’s crush. She desperately wants to go out on dates, but her overprotective father forbids it. Eventually, he decides that he will allow Bianca to start going out with boys… as long as her prickly feminist sister Kate does too. So begins a quintessential rom-com caper. 10 Things is that rarest of teen comedies in that it has aged pretty well, with a killer soundtrack, endlessly quotable script and loveable cast, including Julia Stiles, Joseph Gordon Levitt, Gabrielle Union, and heartthrob-in-the-making Heath Ledger, whose star was about to skyrocket.

She’s All That
(Pygmalion by George Bernard Shaw)

The most famous iteration of Shaw’s classic play is, of course, My Fair Lady, starring Audrey Hepburn. She’s All That transposes the action to a generic Californian high school and casts Rachel Leigh Cook as Laney Boggs, the Eliza Doolittle stand-in. Freddie Prinze Jr, is the jock who makes a wager that he can transform Laney from bespectacled outsider into prom queen. If only he can convince her to remove her glasses!

Easy A
(The Scarlet Letter by Nathaniel Hawthorne)

By the mid-2000s, the trend for literary teen adaptations had died down. But in 2010, the genre was briefly revived by Easy A, a gossip parable which draws inspiration from The Scarlet Letter. Olive is a thoroughly unremarkable girl; not an outcast, but not one of the popular kids either. That is, until she tells a fib about losing her virginity, and finds herself the subject of scandal. This smart satire launched the career of Emma Stone, with supporting performances from the ever-wonderful Lisa Kudrow, Patricia Clarkson and Stanley Tucci.

Honourable mentions must also go to She’s The Man and O, which respectively retell the stories of Twelfth Night and Othello in private schools. A binge-watch of all these films is highly recommended. Or, if you’re short on time, check out Not Another Teen Movie, which parodies pretty much all of them.

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