Film
10 Things I Hate About You
Before it was a rom-com staple, it was Shakespeare's shrew wearing a backpack and a bad attitude, set at a Seattle high school where feminism, mixtapes and a Fabio poster somehow coexist. Sharp-tongued, unexpectedly quotable, and anchored by Heath Ledger's star-making charm, it's the platonic ideal of late-90s teen cinema: funny, a little corny, and sincere about love underneath the sarcasm.
If you liked this
Clueless1995
The other great 90s teen movie built on classic literature, this time Austen's Emma reimagined through Cher Horowitz's shopping mall philosophy. Endlessly quotable, genuinely clever, and just as sweet at its core.
But The fashion and slang are a full time capsule now, which is either charming or distracting depending on your mood.

Cruel Intentions1999
Same year, same teen-Shakespeare energy (this one's Dangerous Liaisons), but curdled into something meaner and more dangerous. Sarah Michelle Gellar and Ryan Phillippe play games that actually have teeth.
But It's genuinely nasty in places — manipulation and cruelty played mostly straight, not just for laughs.

Easy A2010
Emma Stone narrates her own reputation-destroying rumor with the same self-aware wit and literary spine (The Scarlet Letter this time) that made Kat Stratford so much fun to root for.
But It leans harder into direct-to-camera narration and pop culture references, which can feel busier than 10 Things' simpler charm.

The wildcard
Something you would not have found on your own.
The Taming of the Shrew1967
This is the actual Shakespeare play 10 Things I Hate About You is quietly adapting — same shrew, same taming, but performed as fiery adult melodrama instead of high school comedy.
Zeffirelli's lavish adaptation with real-life combustible couple Elizabeth Taylor and Richard Burton, playing the source material 10 Things borrowed from — but as full-blooded, adult, often uncomfortable comedy rather than teen fluff.
But It's theatrical Shakespearean English, slower pacing, and the gender politics are played far more bluntly than the 90s film ever dared.

More like this (8)
Mean Girls2004
If you want the high school ecosystem dissected with surgical precision and quotable one-liners, this is the gold standard — funnier, meaner, and somehow still warm underneath.
But It's more ensemble satire than romance, so if you came for the will-they-won't-they, it's a different flavor entirely.

Bring It On2000
Trades romance for rivalry but keeps the same crackling teen-movie dialogue and confident female lead. It's silly, it's sincere, and it knows exactly what kind of movie it is.
But Cheerleading might not be your thing, and the plot is thinner than 10 Things' — this one's mostly about vibes and one-liners.

Say Anything...1989no page yet
The boombox-over-the-head scene basically invented the modern teen romantic gesture. Lloyd Dobler is the sweet, earnest counterpart to Patrick Verona's bad-boy charm.
But It's quieter and more melancholy than 10 Things, with less comedy and more aching sincerity.
Never Been Kissed1999
Drew Barrymore going undercover as a high schooler is goofier and sweeter, but shares that same late-90s belief that high school romance can actually mean something.
But The central premise — a 25-year-old posing as a teen — hasn't aged gracefully and asks for a lot of suspended disbelief.

She's All That1999
The other iconic 1999 teen makeover movie, all bet-driven bravado and prom-night payoff. If you want more of that exact era's fashion and needle drops, this delivers.
But The 'nerd to knockout' premise is thinner and more dated than anything in 10 Things, with less to say underneath the gloss.

Legally Blonde2001
Not a school romance, but the same DNA of an underestimated woman proving everyone wrong with wit, style, and a lot more brains than anyone gave her credit for.
But It swaps high school for Harvard Law, so the tone is broader and the stakes far sillier.

Kiss Me Kate1953
Same Shakespeare source, same battle-of-wills romance, but reframed as a backstage musical — proof this story has been reinvented across genres for seventy years.
A dazzling Technicolor musical built around a theater troupe staging Taming of the Shrew, with Cole Porter songs doing the work that snarky dialogue does in 10 Things. Pure old-Hollywood spectacle.
But It's a full-blown musical with 1950s sensibilities and stagey theatricality — a big tonal leap from teen naturalism.

Deliver Us from Eva2003no page yet
It's essentially 10 Things' plot mechanics transplanted into an adult, urban rom-com register — same shrew-taming scheme, filtered through a completely different genre and audience.
A grown-up, sexier riff on the exact same setup — a domineering older sister who must be 'handled' so her siblings can date freely — with LL Cool J charming his way through the scheme.
But It's an adult romantic comedy with more explicit content and cynicism than the teen version, and less interested in innocence.
People
Cast
Heath LedgerPatrick Verona
Julia StilesKatarina Stratford
Joseph Gordon-LevittCameron James
Larisa OleynikBianca Stratford
David KrumholtzMichael Eckman
Andrew KeeganJoey Donner
Susan May PrattMandella
Gabrielle UnionChastity
Larry MillerWalter Stratford
Daryl MitchellMr. Morgan
Allison JanneyMs. Perky
David LeisureMr. Chapin
Directing
- Gil JungerDirector
- K.C. ColwellFirst Assistant Director
- Nancy KarlinScript Supervisor
- Darin RivettiSecond Assistant Director
- Sally Sue BeiselSecond Second Assistant Director
Writing
- William ShakespeareTheatre Play
- Karen McCullahWriter
- Kirsten SmithWriter
Production
- Brett BoydstunAssistant Production Coordinator
- Greg SilvermanAssociate Producer
- Donna MorongCasting
- Gail GoldbergCasting
- Marcia RossCasting
- Jody HedienCo-Producer
- Jeffrey ChernovExecutive Producer
- Seth JaretExecutive Producer
- John CatronFirst Assistant Accountant
- Miguel Ángel PovedaPost Production Accountant
- Charles RappPost Production Coordinator
- Andrew LazarProducer
- Katrina ElderProduction Assistant
- Mark AlkoferProduction Assistant
- Michele MehaffeyProduction Assistant
- Denise HeinrichProduction Coordinator
- Blanche Aurore DuaultPublicist
- Ross T. FangerUnit Production Manager
Recommended by
Legally Blonde, A Knight's Tale, Clueless, Mean Girls, Easy A, She's All That, The Taming of the Shrew, The Edge of Seventeen, Booksmart, The Princess Diaries, The Truth About Cats & Dogs, EverAfter, Romeo + Juliet, Much Ado About Nothing, Bring It On, Off Campus, To All the Boys I've Loved Before, The Half of It, Kiss Me Kate, Sixteen Candles, Sierra Burgess Is a Loser, Pretty in Pink, The Breakfast Club, Never Been Kissed, Some Kind of Wonderful