1999 was an amazing year for movies, unleashing such truly iconic cinema as The Matrix, The Sixth Sense, Austin Powers: The Spy Who Shagged Me, and 10 Things I Hate About You.
You might scoff at such a comparison. But nearly 30 years since its debut, 10 Things I Hate About You is still regularly referenced online, be it Heath Ledger's wooing dance across stadium risers or Julia Stiles' eponymous final poem. Written by Karen McCullah Lutz and Kirsten Smith, this inventive and modern adaptation of William Shakespeare's Taming of the Shrew has had us swooning for decades, and counting.
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If Dancing with the Stars, which Stiles is currently competing on, has got you nostalgic for truly terrific and totally entertaining teen movies, we've got you covered. Whether you want to brush up on your Shakespeare, plunge into more hilarious teen heroines' tales, revel in the star power of Ledger and Stiles, or want to remember the highs and lows of high school, we've got you covered with 10 movies like 10 Things I Hate About You.
1. Romeo + Juliet
It's hard to imagine 10 Things I Hate About You would have been made without the runaway success of this Shakespearean adaptation. In 1996, Baz Luhrmann re-imagined the 1597 play in a modern context, where gun-toting, hot-blooded young men favored Hawaiian shirts, and teen love came with a killer soundtrack featuring songs from Garbage, Everclear, and Des'ree. But he kept the language to the original folios, unlike 10 Things.
Leonardo DiCaprio starred as young lover Romeo Montague, who falls hard for Juliet Capulet (Claire Danes), the daughter of a family he's sworn to loathe. But as their romance heats up, so do the tensions between their kinsmen. Blood will spill on both sides, culminating in one of the most tragic moments in all of literature. But props to Luhrmann, for making his Romeo + Juliet distinct, wild, and timelessly cool.
Starring: Leonardo DiCaprio, Claire Danes, Brian Dennehy, John Leguizamo, Miriam Margolyes, Harold Perrineau, Pete Postlethwaite, Paul Sorvino, and Paul Rudd
How to watch: Romeo + Juliet is now streaming on Disney+.
2. She's the Man
Now this Shakespeare adaptation likely got greenlit because of the love for 10 Things I Hate About You. Based on Shakespeare's comedy Twelfth Night, She's the Man stars Amanda Bynes as Viola Hastings, who has dreams of getting a soccer scholarship to college. So, when her school's funding cuts the girls' team altogether, Viola masquerades as her twin brother Sebastian. What could go wrong? Well, for starters, her ruse gets complicated as she feelings grow for soccer team captain Duke Orsino (Channing Tatum).
Screenwriters Ewan Leslie, Karen McCullah Lutz, and Kirsten Smith transported Shakespeare's plot-line of mistaken identities and related shenanigans, but ditched the old-school dialogue in favor of more contemporary conversation. Unapologetically silly, this sports comedy offers lots of fun while you brush up on your Shakespeare. But the best bit is Bynes, who throws herself full-bodied into every gag.
Starring: Amanda Bynes, Channing Tatum, Laura Ramsey, Vinnie Jones, and David Cross
How to watch: She's the Man is streaming on YouTube, free with ads, and on Paramount+.
3. Clueless
Based on Jane Austen's Emma, Clueless is another beloved, '90s-set adaptation of classic literature. Alicia Silverstone stars as Cher Horowitz, the Los Angeles equivalent to an eligible, educated, and yet naive young heroine. At her high school, Cher is pretty, popular, and working hard to get straight A's — even if that means matchmaking her teachers. But her main quest is to turn a hapless and unhip new girl named Tai (Brittany Murphy) into a total Betty.
Rather than capture LA teens of the '90s as they were, writer/director Amy Heckerling dreamed up a fantasy world of enviable fashion, a high-tech closet, cool friends, hoppin' house parties, and truly swoon-worthy crushes. The result was a hit movie that proved aspirational and truly iconic. And for some fans, it was a fun introduction to the world of Austen. A true landmark in teen comedies, Clueless is funny, vibrant, and cool.
Starring: Alicia Silverstone, Paul Rudd, Stacey Dash, Brittany Murphy, Dan Hedaya, Jeremy Sisto, Breckin Meyer, Twink Caplan, Donald Faison, Wallace Shawn, and Elisa Donovan
How to watch: Clueless is now streaming on Paramount+.
4. Easy A
Another book adaptation turned teen movie, Easy A is a 2010 re-imagining of Nathaniel Hawthorne's 1850 novel The Scarlet Letter. Emma Stone stars as Olive Penderghast, a whip-smart 17-year-old girl who gets slut shamed when a prudish classmate starts rumors about her sex life. Rather than denying the claims, Olive leans in, wearing bustiers to school with a red "A" plastered on them, and accepting gift cards in exchange for letting boys lie about hooking up with her.
Written by Bert V. Royal and directed by Will Gluck, Easy A harkens back to the teen sex comedies of the '80s — but with less problematic sexual politics. Stone is sensational in the lead role of a wise-cracking rebel. Penn Badgley pops up as a love interest in a woodchuck costume. And Patricia Clarkson and Stanley Tucci play parents who are beautiful, funny, and cool in a way that's almost infuriating, because we want to go to there! Hilarious and heartwarming, Easy A is a great choice for a girls night in.
Starring: Emma Stone, Penn Badgley, Amanda Bynes, Thomas Haden Church, Patricia Clarkson, Cam Gigandet, Lisa Kudrow, Malcolm McDowell, Aly Michalka, and Stanley Tucci
How to watch: Easy A is now streaming on Paramount+.
5. Save the Last Dance
If you want more of Julia Stiles dancing, you've got to see this 2001 teen drama, co-starring Sean Patrick Thomas (who yes, came out to support her tribute performance on Dancing With the Stars.)
Stiles stars as 17-year-old Sara Johnson, a white Midwestern girl who has ambitions to study ballet at Julliard. However, the unexpected death of her mother not only derails her dreams as she's hit hard by grief, but also forces her to move in with her estranged father, who lives in the South Side of Chicago. Adjusting to inner city life becomes easier when Sara meets Derek (Thomas), a Black classmate who introduces her to hip hop. Opposites attract and the relationship helps Sara get her groove back in this romance that was a smash hit.
Starring: Julia Stiles, Sean Patrick Thomas, Kerry Washington, Terry Kinney, and Fredro Starr
How to watch: Save the Last Dance is now streaming on Disney+.
6. A Knight's Tale
Want more of Ledger in a romantic role with a happy ending? Then, ye, merry lover, should look to A Knight's Tale. Writer/director Brian Helgeland put the rising star in the role of valiant knight, sort of.
Based on Geoffrey Chaucer's 14th-century anthology The Canterbury Tales, A Knight's Tale follows a destitute thatcher's son named William (Ledger) as he squires for a drunken knight. When his master unexpectedly dies, William takes his place in a tourney, chiefly to feed himself and his fellows (Mark Addy and Alan Tudyk). But soon, pretending to be a knight offers him not only fortune and honor, but also the attention of a beguiling noble lady (Shannyn Sossamon).
Blending a 14th century setting with a modern sensibility — including a gleefully anarchistic soundtrack of pop music — A Knight's Tale is terrifically entertaining. Ledger is brooding, beautiful, and solidly funny as the central underdog. Plus, Addy, Tudyk, and Paul Bettany bring solid laughs as William's closest friends.
Starring: Heath Ledger, Mark Addy, Rufus Sewell, Paul Bettany, Alan Tudyk, Shannyn Sossamon, Laura Fraser, Bérénice Bejo, Scott Handy, and James Purefoy
How to watch: A Knight's Tale is now streaming on Paramount+.
7. Josie and the Pussycats
The similarity between 10 Things I Hate About You and Josie and the Pussycats is basically vibes. Based on the Archie comics by Dan DeCarlo, this 2001 musical-comedy follows the titular band, made up of Josie McCoy (Rachel Leigh Cook), Melody Valentine (Tara Reid), and Valerie Brown (Rosario Dawson), as they go from playing a bowling alley to a televised concert that could change the world forever.
Written and directed by Harry Elfont and Deborah Kaplan, this comic book adaptation is totally bonkers, weaving in a parody of 2000s youth culture with a critique of capitalism. It utterly bombed at the box office, but has gone on to build a cult following in part because of its daffy and deranged sense of humor and a slamming soundtrack. Alan Cumming and Parker Posey pop up to play fabulous and scheming record execs. And songs from Letters to Cleo singer Kay Hanley will have 10 Things fans rocking out.
Starring: Rachael Leigh Cook, Tara Reid, Rosario Dawson, Alan Cumming, Parker Posey, Gabriel Mann, Paulo Costanzo, and Missi Pyle
How to watch: Josie and the Pussycats is available for rental or purchase on Prime Video.
8. Juno
In 2007, Elliot Page became a breakout star with his iconic turn as the titular pregnant teen. Written by Diablo Cody and directed by Jason Reitman, this coming-of-age comedy follows Juno MacGruff, a teen who's life is thrown into spin when she accidentally gets her eggo preggo by her crush, Paulie Bleeker (Michael Cera). With the support of her less-than-pleased parents (Allison Janney, and J. K. Simmons), she meets with aspiring adoptive parents, Vanessa and Mark Loring (Jennifer Garner and Jason Bateman). But over nine months, Juno learns a lot about this couple and even more about who she wants to be when she grows up.
Cody won the Best Original Screenplay Oscar for Juno, and it's easy to see why. Rather than trying to encapsulate how teenagers in the '00s were using slang, she made up her own, building a unique world that invited all weirdos in warmly. From there, a vibrant color scheme, a terrific soundtrack from Kimya Dawson, and a cast exploding with chaotic charisma make Juno a timeless tale of growing up.
Starring: Elliot Page, Michael Cera, Jennifer Garner, Jason Bateman, Allison Janney, and J. K. Simmons
How to watch: Juno is available for rent or purchase on Prime Video.
9. The Edge of Seventeen
Named after the Stevie Nicks song, The Edge of Seventeen is a sidesplitting comedy about a 17-year-old girl having a comically rough time. Rocked by the death of her father four years before, Nadine Franklin (Hailee Steinfeld) is a socially awkward misfit who struggles to connect to her image-conscious mom (Kyra Sedgwick) and her popular brother, Darian (Blake Jenner). Plus, she's flailing at getting her crush to notice her. The one person she can depend on is her bestie, Krista (Haley Lu Richardson) — that is, until she catches Krista in bed with Darian.
Feeling betrayed, Nadine has an unhinged (and very funny) crash out, which involves turning to her sardonic teacher (Woody Harrelson) for help. Written and directed by Kelly Fremon Craig, The Edge of Seventeen is a wonderful movie that masterfully captures the agony and outrageousness of being a teen girl trying to make sense of life, loss, and the real meaning of friendship.
Starring: Hailee Steinfeld, Woody Harrelson, Kyra Sedgwick, Blake Jenner, Woody Harrelson, and Haley Lu Richardson
How to watch: The Edge of Seventeen is now streaming on Prime Video.
10. Heathers
If you want a darker spin on boy-meets-girl-and-then-upends-the-high-school-hierarchy, check out Heathers.
Set at Westerburg High School in Sherwood, Ohio, this 1989 dark comedy centers on Veronica Sawyer (Winona Ryder), who is a part of the popular clique of Heather Chandler (Kim Walker), Heather Duke (Shannen Doherty), and Heather McNamara (Lisanne Falk). But Veronica is growing to hate the Heathers for their vanity and cruelty. She finds a twin flame in bad boy J.D. (Christian Slater). Soon, trash talk turns into a comical killing spree.
Definitely darker than 10 Things About You, Heathers is rated R for scenes of violence and irreverent humor around homosexuality, sex, and suicide.
Starring: Winona Ryder, Christian Slater, Shannen Doherty, Lisanne Falk, Kim Walker, and Penelope Milford
How to Watch: Heathers is now playing for free on Tubi.