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f the teen movies of the 1980s were defined by John Hughes, those of the 1990s were best known for their literary links. Many of the period’s most enduring success stories, such as Clueless and 10 Things I Hate About You, took inspiration from works of classic literature and attempted to transfer these well-known stories to high-school settings.

In the late 1990s to early 2000s, a trend emerged for these kind of films, with some of the biggest young stars of the era – Julia Stiles, James Franco, Reese Witherspoon – getting their big breaks in them.

Funny, romantic and filled with teenage angst, they managed to walk the line between light-hearted trash and the kind of film an adolescent could convince an adult they were watching for revision.

While these films were mostly present in the Nineties and Noughties, there were outliers in the teen movie fiction trend, from Nicolas Cage’s turn in Shakespeare-inspired story Valley Girl (1983) to 2010’s Easy A, which both uses and subverts ideas from The Scarlet Letter.

To celebrate the 10-year anniversary of Easy A, here is a ranking of 10 teen movies based on works of classic literature…

10. Whatever It Takes (2000) – Cyrano de Bergerac

While some of the films on this list intelligently twist both the teen movie genre and the classic texts they’re parodying, Whatever It Takes is painfully unimaginative. Loosely based on Edmond Rostand’s 1897 play (loose being the operative word here), it sees high school students Ryan (Shane West) and Chris (James Franco) strike a deal to help the other win their dream girl by pretending to be each other. Rather than being sweet, this film has a constant neggy undertone about being horrible to women, and unfortunately Whatever It Takes manages to be both bland and misogynistic.

9. Sierra Burgess is a Loser (2018) – Cyrano de Bergerac

Another take on the Cyrano tale, this Netflix romcom tells the story of unpopular student Sierra (Shannon Purser) who starts a text relationship with football player Jamey (Noah Centineo) while pretending to be a more popular girl at school. With teen flick To All The Boys I’ve Loved Before having been released a month before, the streaming service clearly hoped their second Centineo vehicle would reach the same levels of success, but the conversations around it tended to be a lot more negative. In an age where catfishing and consent are rightly being discussed, the romanticisation of Sierra’s manipulative behaviour just didn’t sit right with audiences. 18 years after the release of Whatever It Takes, Netflix really should have known better.

As a modern retelling of Cyrano de Bergerac, ‘Sierra Burgess is a Loser’ struggles to make its source material acceptable for modern audiences
As a modern retelling of Cyrano de Bergerac, ‘Sierra Burgess is a Loser’ struggles to make its source material acceptable for modern audiences(Netflix)

8. She’s The Man (2006) – Twelfth Night

Of all Shakespeare’s plays, Twelfth Night might not be the most obvious subject to receive the high-school treatment. However, with its love triangles upon triangles, gender swapping and trickery, it does make for a pretty fun comedy. But where the core text is complex, She’s The Man uses a simple script to make it that bit more palatable. Amanda Bynes is tomboy Viola, who disguises herself as her twin brother Sebastian and attends boarding school in his place so that she can play on the school’s football team after the girls team is cut. She quickly finds herself falling in love with team mate Duke Orsino, but he’s got his eye on another girl called Olivia, who unfortunately has a crush on Viola-as-Sebastian. Hijinks ensue, but everyone gets their happily-ever-afters in the end.

7.  O (2001) – Othello

Where there’s a light-hearted comedy element to most of the teen movies on this list, O is an outlier in its serious tone. Othello is now basketball player Odin (Mekhi Phifer), who is manipulated by Hugo (Josh Hartnett) to believe that girlfriend Desi (Julia Stiles) is cheating on him with his teammate Michael (Andrew Keegan). It’s a hard-hitting, but fairly faithful adaptation of Shakespeare’s drama, with sexual assault, murder and suicide storylines, but it struggles to look more deeply at the ways in which race and sex exist in modern society. It’s a standard you wouldn’t hold the other films on this list to, but O takes itself so seriously you kind of have to.

'O' is far more serious than its comedy counterparts
‘O’ is far more serious than its comedy counterparts(Rex Features)

6. Valley Girl (1983) – Romeo and Juliet

As the original drama is about love-obsessed, overly dramatic teens, it’s no surprise that Romeo and Juliet-esque storylines have wormed their way into many a teen movie. In this 1983 classic, Deborah Richman is titular Valley girl Julie, who falls in love with a far-too-old-to-be-in-high-school Nicolas Cage as Randy. As a punk from the city, he’s her bit o’ rough, but the “two households, both alike in dignity” keeping them apart aren’t their families, but their friends. Things are kept light, with Romeo and Juliet’s tragic ending avoided, but with its sharp script and the great chemistry between the pair, it clearly paved the way for the teen movie classic lit trend of the 1990s.

5. She’s All That (1999) – Pygmalion

The best known adaptations of George Bernard Shaw’s Pygmalion are undoubtedly My Fair Lady and Pretty Woman, but 1999’s She’s All That is a great look at the play, too. Freddie Prinze Jr is jock Zack, who attempts to regain his popularity after being dumped for a reality star with a bet. If he can turn nerdy art student Lainey (Rachael Leigh Cooke) into the prom queen, he’ll be restored. Nobody is going to watch this film and think that Leigh Cook is unattractive just because she’s wearing glasses, but Zack manages to stay on the right side of likeable and leaves you rooting for him. Bonus points for Prinze’s performance art routine involving a hacky sack, it’s a true work of art.

Glasses do not a nerd make: Rachel Leigh Cook in 'She's All That'
Glasses do not a nerd make: Rachel Leigh Cook in ‘She’s All That’(Miramax Pictures)

4. Cruel Intentions (1999) – Les Liaisons Dangereuses

Based on a 1782 novel, Cruel Intentions transposes the world of French nobility to rich kids in New York. Sarah Michelle Gellar and Ryan Philippe are step-siblings Kathryn and Sebastian, who engage in a game of sex manipulation to get vengeance on those who’ve wronged them. For Sebastian, his challenge is to woo Annette (Reese Witherspoon), their new headmaster’s daughter who’s sworn to be celibate until marriage. If he seduces her, he’ll be able to have the person he’s always wanted: his not-quite-sister. The power games played between the pair are enthralling to watch and despite featuring a seriously dramatic ending, there’s just enough pent up angst in this film to make it irresistible.

Sarah Michelle Gellar and Ryan Phillippe play sex-obsessed step siblings in 'Cruel Intentions'
Sarah Michelle Gellar and Ryan Phillippe play sex-obsessed step siblings in ‘Cruel Intentions’(Rex Features)

3. Easy A (2010) – The Scarlet Letter

“Isn’t it always the way, the books you read in class always seem to have some strong connection with whatever angsty drama’s going on,” Emma Stone’s Olive Penderghast asks in Easy A she reads The Scarlet Letter, setting up a film that won’t just take inspiration from classic literature, but parody the entire genre. A film about teens having sex – or rather, teens lying about having sex – Easy A reclaims Nathaniel Hawthorne’s 1850 morality tale as a feminist message about liberation and owning yourself, while also paying homage to the teen movies of the Eighties. It’s the film that Stone was born to play and made her a star.

2. Clueless (1995) – Emma

Clueless reimagines Jane Austen’s Emma as though it was, like, totally transposed to Beverly Hills. Alicia Silverstone plays Cher, a popular, spoiled teen who takes new student Tai (the late Brittany Murphy) under her wing, giving her a makeover only to find herself later rejected. Aesthetically, Clueless is up there with the greats, with outfits still being recreated today and hilarious technology. But, like Cher, there’s more to this film than meets the eye and the sharp script and zingy one liners keep it feeling fresh today.

Patrick (Ledger) tames the shrew in '10 Things I Hate About You'
Patrick (Ledger) tames the shrew in ’10 Things I Hate About You’(Buena Vista)

1. 10 Things I Hate About You (1999) – The Taming of the Shrew

It couldn’t be anything else at the top of this list, could it? 10 Things I Hate About You is often lauded as the ultimate teen romcom and it’s easy to see why. Julia Stiles is the titular shrew Kat, a “heinous b****” and moody teen with no interest in dating who’s seduced by school slack Patrick (Heath Ledger) to help out a friend. The chemistry between Stiles and Ledger is strong, but with a supporting cast including Gabrielle Union and Joseph Gordon Levitt, it’s hard not to fall in love with this film. It perfectly captures the dizzy rush of first love, with regular allusions to The Taming Of The Shrew as Gordon Levitt captures his lovesickness with the words: “I burn, I pine, I perish.” But it’s Ledger who really drives 10 Things I Hate About You. This is the Australian actor at his best: singing, dancing, smiling, and making audiences around the world fall in love with him.

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