The Best Teen Movie Adaptations of Shakespeare

The work of William Shakespeare is often involuntarily thrust upon unsuspecting teenagers, embedding itself into the emotional tapestry of adolescent life. Considering the earnestness of his dramas and the wackiness of his comedies, it’s not surprising that this demographic is exposed to such a distinctive creative voice, welded to the emotional expanse of his worlds. His writing is not just taught to high schoolers, it is also frequently centered on the lives, loves and infatuations of youth. His plays are about the thin veneer of control which holds together an apocalyptic storm of emotions. It isn’t necessarily true that teenagers move through the world uninhibited (I don’t know about you, but I was inhibited by numerous dumb things), but the divide between how teenagers want to be seen and how teenagers feel is substantial and vulnerable—a single, inflexible layer, brittle with a lack of practice. Shakespeare knew that this truth is buried beneath layers of grown-up ease. As such, filmmakers have been reinterpreting his material, often offering it back to the young people who so preoccupied him. Teen Shakespeare adaptations had a marked heyday, but they’ve spanned multiple decades as directors have sought to bring his work to the lives of modern high schoolers.

Here are the best teen movie adaptations of Shakespeare:

10. A Midsummer Night’s Rave (2002)

Director: Gil Cates Jr.

It is the early 2000s. A bunch of teenagers want to get high and ignore the monotony of their crushes, breakups and disappointments. On its face, A Midsummer Night’s Rave seems to be one of the most thoughtful ways of addressing the odd, unruly plot of A Midsummer Night’s Dream. Rather than the spell of a fairy queen, the mix of hallucinogenic drugs leaves these characters stranded across a sprawling party, locked into unique patterns that leave them reacquainted with past flings and new romances. In many ways, this is the ideal for a modern reinterpretation of classic material: New and young, locked into a specific historical moment. Unfortunately, the lackluster filmmaking from director Gil Cates Jr. undermines the end result, flattening its aesthetic into ugly, over-lit images. A Midsummer Night’s Rave proves to be more of an interesting idea than an interesting film.

9. O (2001)

Director: Tim Blake Nelson

In 2001, George W. Bush was president, Destiny’s Child had opened their best-selling single “Independent Women” by listing the cast of Charlie’s Angels (brilliantly rhyming “Cameron D.” with “Destiny”) and you could listen to said song on the newly launched iPod, which promised to store up to 1,000 songs. Also O was released, a cinematic relic of 1999, intentionally postponed after the real-life Columbine school shooting strayed eerily close to the film’s plot of a student’s desire to fatally rearrange the school’s social hierarchy. O is just one of the modern adaptations Julia Stiles embarked upon, bringing Othello’s infamously tragic heroine Desdemona to life. As Desi, Stiles is as self-possessed and sweet as Hugo (Josh Hartnett) is sulky, rudely talking back to a barking Martin Sheen (who plays Hugo’s father, Coach Duke). Meanwhile, Mekhi Phifer is charming—if a little underwritten—as the titular O (short for Odin). Despite the array of good intentions, Othello is source material burdened by its violent history, flattening any future takes and leaving O as one of its self-serious victims. None of the deadly stakes are redesigned to fit the context of high school life, with every fatal act thrust upon unsuspecting adolescent lives. Still, there is a lot to admire in this project’s ambition and its array of appropriately committed performances.

8. Just One of the Guys (1985)

Director: Lisa Gottlieb

On some level, all of Shakespeare’s plays (tragedy and comedy alike) are about the process of discovering identity, negotiating the requirements of seeing and being seen, whether it’s Hamlet desperate to reassert himself in his family lineage or Julius Caesar attempting to tie his reputation to Rome’s reputation. In Twelfth Night, this is explored through gender, resting on the nexus of men and women and the distinctions therein. Shakespeare’s control of pacing lends itself to a tapestry of increasingly fraught and funny reveals throughout the story, cementing it as one of the great on-stage romantic comedies. Yet in every modern update, the story’s stale gender politics (and preoccupation with genitalia) undermines the scope of this unconventional romance. This feels especially true for Just One of the Guys, which is gripped by the stilted pacing of low-budget ‘80s movies. Still, this lurching tempo (between the grounded feminist logic of its protagonist to the barely-there stereotype of the younger brother) also serves the film, lending it a kind of honesty and energy that feels in line with the spontaneity of the characters who make a series of strange, inexplicable decisions. Director Lisa Gottlieb never strays from Terry’s (Joyce Hyser) perspective, letting her vantage point fill the screen and anchor the audience. As a result, Just One of the Guys transcends its more muddled (and thoroughly ’80s) expressions of gender equality to be an outing worthy of the teen canon.

7. John Tucker Must Die (2006)

Director: Betty Thomas

As a take on one of Shakespeare’s more slight comedies, John Tucker Must Die drags the zany 16th century plot of The Merry Wives of Windsor into the early 21st century. It is a classic 2000s teen comedy, complete with low-rise jeans, abrasive needledrops and (non-era specific) thinly veiled misogyny. The wronged girlfriends of John Tucker (Jesse Metcalfe) unite to shatter his sterling reputation, utilizing Kate’s (Brittany Snow) inexplicable ugly duckling image to ensnare him. Director and screenwriter Betty Thomas molds a great adaptation, offering this material back to a generation who’s image of Shakespeare was one of dusty folios rather than sexy hijinks. Unfortunately, the film can’t really transcend the broad comedic beats, familiar to consumers of big-budget noughties comedies. The four main actresses feel fundamentally disconnected, with each of their performances locked into a separate film. Their eventual friendship arrives unexpectedly, bound by nothing but their shared time on screen. With this, the internal logic of the film collapses. Still, John Tucker Must Die is an easy watch, stranger than some of its contemporaries.

6. She’s the Man (2006)

Director: Andy Fickman

If you were a teenage girl who frequented middle school slumber parties in the late-noughties, chances are that you have seen She’s the Man more times than you can count. While much of it doesn’t necessarily hold up–with an all-consuming obsession with men and women and the differences therein. Yet it distinguishes itself through its lead performances. Amanda Bynes would have shined as a vaudeville star; the succession of Twelfth Night hijinks pulls out new expressions that stretch across her whole body, making for comedy that feels reminiscent of the stage performers who first embodied Shakespeare’s vision. Thanks to her and co-star Channing Tatum, there is genuine romance in She’s the Man, largely due to the strange and charming friction between these actors—with Bynes’ wackier take elevating Tatum’s more lived-in, relaxed embodiment of the romantic lead. In the end, their relationship overwhelms the stranger, more sitcom-y (featuring several heavily signposted reveals and miscommunications) final act.

5. Get Over It (2001)

Director: Tommy O’Haver

A Midsummer Night’s Dream is an odd text to submit to this trend, a dreamy and expansive fable squeezed into the tight, angular hallways of the average American school. But Get Over It director Tommy O’Haver carefully negotiates this tone, crafting a film that feels as wacky as it does sweet and honest. The cast is sprawling—a who’s who of teen A-listers, ranging from Kirsten Dunst and Mila Kunis to Zoe Saldaña and Sisqó—but the quick cuts and playful framing accommodate the unique ensemble and keep this bizarre plot chugging along. All of the confusing hijinks are rendered inconsequential in light of the actors’ lovely chemistry and their realistic, era-appropriate banter. You may think you are watching this for an update to one of the world’s most famous comedies, but you will be met with silly, thoroughly ‘00s fun, culminating in the choreographed “September” number which closes the film.

4. Valley Girl (1983)

Director: Martha Coolidge

This is somewhat of a cheat, as Romeo and Juliet is already a text about the romance of being young, dumb and horny, yet Valley Girl feels like an honest reinterpretation of one of the world’s most famous tragedies. It’s just a thoroughly ‘80s spin on that familiar play. Deborah Foreman is the bubbly Julie, whose eyes are perpetually shining with youthful earnestness, and Nicolas Cage is the gruff Randy, whose well-practiced ease is concealing something sweeter and less metallic. Director Martha Coolidge’s take would fall apart if Foreman and Cage’s chemistry wasn’t so winning. These are two teenagers whose sense of themselves is still malleable enough to allow for something unexpected, and any latent guardedness dissipates under the aggressive lights of a fateful house party. They are just happy to talk to one another, to listen to pop music over the radio and drive around, to gaze dazedly at the other. In turn, we are happy to gaze right back.

3. China Girl (1987)

Director: Abel Ferrera

Under Abel Ferrera’s guidance, Romeo is Tony (Richard Panebianco), a New Yorker and a lifelong Little Italy resident and Juliet is Tye (Sari Chang), a daughter of Hong Kong immigrants, living in the gradually expanding Chinatown. As these city blocks grow and shrink according to socio-economic shifts, these characters are beckoned closer. Fate (or New York’s city planners) bring them together. Obviously, this is yet another version of Verona’s star-crossed lovers, so it is worth considering why this play is so breathlessly seized upon by filmmakers. Part of this is Romeo and Juliet’s simplicity; its beats are so broad and recognizable that, as a viewer, it is hard to ascertain when it is being referenced and when a tragic love story is just a tragic love story. But the play’s appeal runs deeper, stretching into every romantic subgenre. Many argue that Romeo and Juliet is proof that love is similar to hate, but really love, hate and adolescence sit alongside one another, a tight, uncomplicated triangle that makes for a thrilling watch. Shakespeare wrote a story about how being young and bored are sometimes enough to make you fall in love. Its long-term appeal is as reliable as its honesty. China Girl stays true to this, but offers another facet to such a compelling argument: Sometimes love is born on the dance floor, after eyeing someone with a similarly faded leather jacket and back-combed ‘do.

2. 10 Things I Hate About You (1999)

Director: Gil Junger

“I burn, I pine, I perish,” waxes a lovestruck Cameron (Joseph Gordon-Levitt) upon first spotting the gorgeous and popular Bianca Stratford (Larisa Oleynik). It is a wondrously unkempt way of expressing attraction—a strange, timeless observation, born from his unawareness and his film’s self-awareness. 10 Things I Hate About You is potentially the most famous of the teen Shakespeare movie trend, a pitch-perfect melding of creative intentions. In this outing, Shakespeare’s The Taming of the Shrew is met with a light, breezy rhythm, deliberately positioned away from some of the darker aspects of its origin story (unlike O). Bianca and Cameron’s love story is sweet, but that between Kat (Julia Stiles) and Patrick (Heath Ledger) is iconic. Two great actors, with markedly different screen presences, collapse into one another, crafting a host of unforgettable moments that feel otherworldly, independent of any day-to-day logic. Why do they have to sail to the paintball park where they have their first date? How far is it from Kat’s house, where they end up? None of this matters! All of it is bound together by the wattage of their star power, forceful enough to cast aside any rules of logic or geography—much like the teen love it so deftly depicts.

1. My Own Private Idaho (1992)

Director: Gus Van Sant

In positioning Henry IV(s) and V in the ‘90s, filmmaker Gus Van Sant gives the relationship between Scott Favors (Keanu Reeves) and the tortured Mike Waters (a devastating River Phoenix) room to shift and grow. Phoenix’s performance is gentle and determinedly dedicated, absorbing Scott and mimicking him in barely perceptible ways. They are two hustlers, traversing America as sex workers bound by a similarly anarchist worldview. And yet their backgrounds are markedly split, with Scott being the wealthy son of a mayor and Mike being the son of a penniless woman now consigned to fading memories. Through these boys, Van Sant reanimates the original text, breathing new, romantic life into it. Speaking especially of the teen Shakespeare trend, there has been a divide between what makes a great adaptation and what makes a great film. Great adaptations reset the stakes to fit a new world, taking something hard, dusty and unbreakable and holding it up to dancing light; great films feel more subjective, imbuing the formally excellent adaptation with feeling and life. My Own Private Idaho is the best of both, switching effortlessly between something near and real and something lofty and grand, indicative of the past it was born from. Like a fever dream or the reveries of your teens, My Own Private Idaho exists above logic and space. It infects us before leaving us awake with blurred vision, disorientedly stumbling back into real life, like Mike himself.

London-based film writer Anna McKibbin loves digging into classic film stars and movie musicals. Find her on Twitter to see what she is currently obsessed with.