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Why Are the Best Teen Movies Based on Classic Literature?

It only makes sense that a genre dealing in emotions as old as time would take cues from writing that’s practically just as dated

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Tied to the 20th anniversary of Bring It On, we hereby dub the next five days Teen Movie Week. Dig up your varsity jacket, pull up to your cafeteria table, and relive your adolescence as we celebrate the best coming-of-age movies ever made.

A good teen movie deals with themes as old as time: coming of age, the thrill of first love, jealousy, bitterness, and other emotions the hormone-addled brain is barely equipped to process. Which may explain why many of the best teen movies are based on stories that, while not quite as old as time, are often several centuries older than their adolescent protagonists.

Though their surfaces may be decorated with contemporary slang and style choices, many classic teen movies are rooted in even more classic works of literature. Baz Luhrmann’s Romeo + Juliet came out in 1996, but the William Shakespeare play it transplants to “Verona Beach”—in reality a mashup of Miami and Mexico City—debuted in the late 16th century. So did The Taming of the Shrew, which went on to inspire 10 Things I Hate About You; gender-swapping comedy Twelfth Night, from the early 17th century, is the basis of She’s the Man, from 2006. Shakespeare dominates this subgenre, but it’s hardly limited to his work. (It couldn’t be; 37 plays are hardly enough to satisfy an industry of studio executives rushing to get in on a trend.) Clueless (1995) is a play on Emma (1815). Cruel Intentions (1999) adapts the French epistolary novel Les liaisons dangereuses (1782). Easy A (2010) is derived from Nathaniel Hawthorne’s Scarlet Letter (1850). And those are just the enduring staples that made The Ringer’s 64-film bracket; like every phenomenon, the teen classics craze was bolstered by lesser entries like O (2001), a melodramatic rendition of Othello set on a high school basketball team, and a modern reboot of Hamlet—sometimes known as Hamlet 2000—starring Ethan Hawke.

Adaptations of literary touchstones are, of course, a classic source of new content. A narrative as potently simple as Romeo and Juliet—two attractive people manage to be attracted to each other despite their families’ mutual hatred—is too catchy not to be endlessly riffed on. (It also helps that, like many works predating modern copyright law, the tragedy is a piece of public domain.) A filmed version of West Side Story hit theaters in 1961, and will again later this year barring pandemic-related delays. Richard III became an off-Broadway production called Teenage Dick in 2018; Netflix has not one but two youthful spins on Cyrano de Bergerac: Sierra Burgess Is a Loser and The Half of It.

The teen classic boom is at the apex of two overlapping trends. One trend is the golden age of teen movies as a whole in the late ’90s and early aughts, as marked by this week’s 20th anniversary of Bring It On. The other was a wider interest in newer takes on older stories, not all of which were marketed at high schoolers. (The Lion King, after all, is technically a PG interpretation of Hamlet and came out a full year before Clueless.) “There was such a big teen movie explosion at the time,” said 10 Things About You cowriter Kirsten Smith in an oral history by The New York Times. “It was very unusual you would get your first script made, let alone green-lit six months after it was optioned.” But “Taming of the Shrew with a budding feminist in ’90s Seattle” was too of-the-moment not to fast track.

At a certain point, the template became so ubiquitous that Easy A, the latest and most meta of the bunch, had to make a joke about it: “Isn’t that always the way?” Emma Stone’s Olive Penderghast asks. “The books you read in class always seem to have some connection to whatever angsty adolescent drama is going on?” Maybe not in real life, but certainly in movie scripts.

Besides the zeitgeist, though, what makes the teen movie and the classic literary adaptation such a fitting match? Perhaps, as Olive notes, it’s because the very books that films like Easy A and Clueless are based on are also the ones their target audience are currently assigned to read in class. English class curricula are such that few Americans are as likely to be currently reading Austen, Hawthorne, or the Bard as a precocious 16-year-old. (Like all films with an even vaguely educational hook, there’s also a ready-made secondary market of overworked teachers looking to fill a couple days in their lesson plan.) It’s only natural for teens to gravitate toward plot points they’ve already learned to recognize.

Still, it doesn’t take an English degree to grasp the stakes of “boy meets girl.” Part of what the teen classic does is translate perennial problems into more modern terms. From the Renaissance through the Regency, marriage was the be-all, end-all of any romantic farce, and with good reason; matrimony at the time was as much a legal and economic alliance as an emotional bond, and the only kind women were in any position to forge. That’s less the case in a world with no-fault divorce and women with their own bank accounts, but a high school comedy lets commitment feel like as big a deal as it once was, even if a kiss no longer comes with a lifetime partnership. (To a teenager, any kind of love feels life-altering.) Romeo and Juliet are canonically just out of the 14th-century Italian version of junior high; casting a baby-faced boy wonder like Leo DiCaprio isn’t revisionist—it’s as faithful as it gets.

Like all adaptations, the teen classic also allows for subversion as well as dutiful translation. 10 Things I Hate About You, in particular, turns its misogynist blueprint—there’s a sexist smear in the name!—on its head. The actual Taming of the Shrew has Kat Stratford literally beaten into submission, a disturbing scenario originally played for laughs. 10 Things makes Kat slightly insufferable and even calls her out for her self-righteous privilege, but mostly sees her principles and stubbornness as virtues to be rewarded with a partner who sees her for who she is. (Kat is played by Julia Stiles, who also appears in O and Hamlet 2000, making her the genre’s unofficial frontwoman.) In She’s the Man, Viola’s cross-dressing is motivated by a desire to prove she’s as good at soccer as her priggish ex-boyfriend. Meeting a pre–Step Up Channing Tatum while she’s there is just a bonus.

Not all transitions are so seamless; in fact, the awkwardness of projecting old-time social mores onto unruly teens is often part of the joke. Even kids with as much wealth and free time as those on the Upper East Side aren’t playing sexual power games before they’re old enough to vote, though don’t tell that to Cruel Intentions. (Judging by its success and clear influence on successors like Gossip Girl, realism is overrated.) Nor is Emma’s self-satisfied meddling as believable from even a queen bee like Cher Horowitz; then again, neither is a computer-powered outfit assembler.

In theory, the teen classic sounds like the movie version of those mommy-blog recipes that trick toddlers into eating vegetables by blending zucchini into a brownie. In practice, they’re less about getting high schoolers to hit the library than combining the best of both worlds: the timeliness that comes with using swiftly dated reference points like low-rise jeans, plus the timelessness that comes with cribbing from enduring stories. All teen comedies benefit from a sense of heightened reality—all the better to sell 20-something actors recreating their adolescence. Pulling from one’s bookshelf is just an easy—and more importantly, proven—shortcut.