Film

10 Things I Hate About You

Name: 10 Things I Hate About You
Genre: Comedy, Romance, Drama
Released: 1999
Cast: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, Larisa Oleynik, David Krumholtz

Other titles called 10 Things I Hate About You: the 2009 series (Freeform).

Romantic comedy
Comedy
Light-hearted

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.

TMDb rating

3.8

Should you watch it?

Watch it if you love a teen romcom that is sharp, quick and secretly tender, with a Shakespearean plot wrapped in punchy 1999 dialogue and characters who argue their way toward each other.

Skip it if you find high-school comedies wearing thin, or you want a film where the wit never softens into sincerity, since its heart shows up earlier and more often than its jokes.

What it asks of you: Under ninety-840 minutes of attention is all it needs, moving briskly from one scene to the next with little patience for quiet stretches, and it keeps its tone light even when the characters are miserable.

Not sure? Find tonight's pick in a minute.

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.

Not sure tonight? Get a pick in a minute, starting from 10 Things I Hate About You

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.

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...1989

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 Eva2003

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.