IIf the teenage movies of the 1980s were defined by John Hughes, those of the 1990s were best known for their literary connections. Many of the most enduring success stories of the period, such as Distraught and 10 things I hate about you, was inspired by works of classical literature and tried to transfer these well-known stories to schools.

In the late 1990s and early 2000s, a trend emerged for this genre of films, with some of the biggest young stars of the time – Julia Stiles, James Franco, Reese Witherspoon – getting their big breaks there.

Funny, romantic, and filled with teenage angst, they were able to distinguish between light waste and the kind of movie a teenager could convince an adult that they were watching for a review.

While these films were mostly present in the 90s and 2000s, there were some outliers in the teenage fiction trend, of Nicolas Cage’s turn in a Shakespeare-inspired story. valley girl (1983) to the 2010s Easy, which uses and subverts the ideas of The scarlet letter.

To celebrate 10 years of Easy, here is a ranking of 10 films for teenagers based on works of classic literature …

10. Anyway (2000) – Cyrano de Bergerac

While some of the films on this list cleverly distort both the genre of teen films and the classic texts they parody, Whatever the cost is painfully unimaginative. Loosely based on Edmond Rostand’s 1897 play (the keyword here is loose), it sees high school students Ryan (Shane West) and Chris (James Franco) strike a deal to help the other win the girl of their dreams. pretending to be each other. Rather than being meek, this movie has a constant negative connotation of being horrible with women, and sadly Whatever the cost manages to be both bland and misogynistic.

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

Another side of Cyrano’s story, this Netflix romcom tells the story of unpopular college student Sierra (Shannon Purser) who begins a textual relationship with soccer player Jamey (Noah Centineo) while claiming to be a more popular girl. at school. with teen movie To all the boys I’ve loved before having released a month before, the streaming service was clearly hoping its second Centineo vehicle would achieve the same levels of success, but conversations around it tended to be much more negative. In an era when catfish and consent are rightly discussed, the romance of Sierra’s manipulative behavior just didn’t sit well with audiences. 18 years after leaving Whatever the cost, Netflix really should have known.

As Cyrano de Bergerac’s modern tale, “Sierra Burgess is a Loser” struggles to make its source material acceptable to modern audiences.


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

Of all Shakespeare’s plays, Twelfth Night might not be the most obvious subject to receive treatment in high school. However, with its love triangles upon triangles, gender swap, and trickery, it makes for quite a fun comedy. But where the basic text is complex, She is the man uses a simple script to make it a bit more palatable. Amanda Bynes is the tomboy Viola, who dresses up as her twin brother Sebastian and attends boarding school instead so she can play on the school’s football team after the girls’ team is dropped. She quickly falls in love with her teammate Duke Orsino, but he has an eye on another girl called Olivia, who unfortunately has a crush on Viola-as-Sebastian. Hijinks ensue, but eventually everyone gets their happiness.

7. O (2001) – Othello

Where there is an element of light comedy in most of the teen movies on this list, oh is an outlier in its serious tone. Othello is now basketball player Odin (Mekhi Phifer), who is manipulated by Hugo (Josh Hartnett) into believing that his 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 tales of sexual assault, murder and suicide, but it struggles to take a deeper look at how race and gender exist in society. modern. It’s a standard you wouldn’t want to hold the other movies on this list to, but oh take yourself so seriously that you have to do it.

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‘O’ is way more serious than its comedic counterparts

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6. Daughter of the Valley (1983) – Romeo and Juliet

As the original drama is about love-obsessed and overly dramatic teenagers, it’s no surprise that Romeo and Juliet-Esque storylines have crept into many teen movies. In this 1983 classic, Deborah Richman is Valley’s titular daughter Julie, who falls in love with Nicolas Cage far too old to be in high school as Randy. As a city punk he is a bit harsh, but the “two homes, both equal in dignity” that separate them are not their families, but their friends. Things stay light, with Romeo and JulietThe tragic ending of evaded, but with its sharp storyline and the great chemistry between the two, it clearly set the stage for the classic ’90s teen movie trend.

5. She’s All That (1999) – Pygmalion

The most famous adaptations of George Bernard Shaw Pygmalion are undoubtedly My beautiful lady and Attractive Women, but the years 1999 She is all that is also an excellent overview of the play. Freddie Prinze Jr is jock Zack, who is trying to regain his popularity after being dumped for a reality TV star with a bet. If he can turn nerdy art student Lainey (Rachael Leigh Cooke) into a prom queen, he will be restored. No one is going to watch this movie and think Leigh Cook isn’t attractive just because she wears glasses, but Zack manages to stay on the good side of likable and lets you root for him. Bonus points for Prinze’s performance art routine involving a hacky sack, this is a true work of art.

Glasses don’t make a nerd: Rachel Leigh Cook in ‘She’s All That’

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4. Cruel Intentions (1999) – Dangerous Liaisons

Based on a novel from 1782, Cruel intentions transposes the world of the French nobility to the rich kids of New York. Sarah Michelle Gellar and Ryan Philippe are half-siblings Kathryn and Sebastian, who engage in a game of sexual manipulation to get revenge on those who have wronged them. For Sebastian, his challenge is to woo Annette (Reese Witherspoon), the daughter of their new manager who has sworn to be single until marriage. If he seduces her, he can have the person he always wanted: his not quite sister. The power games played out between the two are thrilling to watch and despite a very dramatic ending, there is just enough pent-up angst in this film to make it irresistible.

Sarah Michelle Gellar and Ryan Phillippe as sex-obsessed step-siblings in ‘Cruel Intentions’

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3. Easy A (2010) – The Scarlet Letter

“Isn’t it always the case, the books you read in class always seem to have a strong connection to the agonizing drama that is going on,” asks Emma Stone’s Olive Penderghast in Easy she reads The scarlet letter, setting up a film that will not only draw inspiration from classical literature, but parody the whole genre. A movie about teens having sex – or rather, teens lying about having sex – Easy picks up Nathaniel Hawthorne’s moral tale of 1850 as a feminist message about liberation and self-possession, while also paying homage to the teenage movies of the ’80s. It is the film that Stone was born to play and made of. ‘she a star.

2. Clueless (1995) – Emma

Distraught reinvents Jane Austen Emma like it’s, like, totally transposed to Beverly Hills. Alicia Silverstone plays Cher, a popular and spoiled teenager who takes new college student Tai (the late Brittany Murphy) under her wing, giving her a makeover only to find herself later rejected. Aesthetically, Distraught is among the greats, with outfits still recreated today and some hilarious tech. But, like Cher, there’s more to this movie than it looks and the sharp script and tangy linings make it feel fresh today.

Patrick (Ledger) tames the shrew in ’10 Things I Hate About You ‘

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1. 10 Things I Hate About You (1999) – The Tame Shrew

It couldn’t be anything else at the top of this list, could it? 10 things I hate about you is often considered the ultimate teen romantic comedy and it’s easy to see why. Julia Stiles is the titular shrew Kat, an obnoxious “b ****” and cranky teenager with no interest in dating who is seduced by 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 vertigo of first love, with regular allusions to The Tamed Shrew as Gordon Levitt captures his heartache with the words: “I burn, I die, I perish.” But it’s Ledger who really drives 10 things I hate about you. He’s the Australian actor at his best – singing, dancing, smiling and making audiences around the world fall in love with him.