The closest movies to 10 Things I Hate About You are She’s All That, Clueless, Drive Me Crazy, and Deliver Us from Eva. Each shares some of the 1999 film’s essential ingredients: a high-school or relationship scheme, sharp social comedy, romantic tension, strong personalities, and characters learning to look beyond the roles other people assign them.
But no single movie completely duplicates 10 Things I Hate About You. Its particular mix of Shakespearean structure, rebellious femininity, sisterhood, family conflict, Heath Ledger’s romantic charm, witty dialogue, and late-1990s soundtrack nostalgia is unusually specific. So this guide groups the best choices by the part of the film you want to revisit.
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The closest matches
1. She’s All That (1999)
If you want another late-1990s high-school romance with prom-season stakes, popularity politics, a social bet, and a couple who gradually sees past appearances, start here. Freddie Prinze Jr. plays a popular student who accepts a challenge to transform an unpopular classmate into prom queen, while the relationship becomes more complicated than the original scheme suggests.
Like 10 Things I Hate About You, it modernizes a classic work of literature—in this case, elements of George Bernard Shaw’s Pygmalion. Its makeover premise and beauty standards feel more dated and conventional, however, and its heroine is less confrontational than Kat Stratford.
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Best for: prom nostalgia, makeover plots, popularity drama, and a straightforward 1990s teen romance.
2. Clueless (1995)
Clueless is an essential companion to 10 Things I Hate About You: both are stylish 1990s high-school comedies that update classic literature for a contemporary teenage world. Amy Heckerling’s film reworks Jane Austen’s Emma through Cher Horowitz, a wealthy and socially influential student whose confidence does not prevent her from misunderstanding her own emotional life.
It is lighter and more comedy-forward than 10 Things, but the similarities are substantial: fast dialogue, memorable fashion, social maneuvering, a charismatic young heroine, and a coming-of-age story hidden inside a romantic comedy.
Best for: clever banter, fashion, literary adaptations, and a heroine whose self-knowledge develops gradually.
3. Drive Me Crazy (1999)
Choose Drive Me Crazy when the fake-dating setup is the part of 10 Things I Hate About You you want most. Melissa Joan Hart and Adrian Grenier play former friends who pretend to date in order to provoke jealousy and improve their social standing. As expected, the artificial relationship begins to feel real.
The film has the heightened emotions, school-clique politics, jealousy, and polished teen-rom-com machinery associated with the period. It is less literary and less edgy than 10 Things, but its enemies-to-lovers and pretend-romance elements make it one of the closest structural matches.
Best for: fake dating, former friends becoming romantic partners, and pure late-1990s teen-movie atmosphere.
4. Deliver Us from Eva (2003)
This is the closest recommendation in terms of source material: it is also based on Shakespeare’s The Taming of the Shrew. Gabrielle Union plays Eva, a formidable, perfectionist woman whose family and friends arrange a courtship scheme involving LL Cool J because they believe a romantic partner will make her less controlling.
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Unlike 10 Things I Hate About You, this is an adult romantic comedy rather than a high-school story. Its early-2000s Black rom-com identity, family dynamics, and central performance give it a personality of its own. The premise also invites a useful comparison: both films play with the idea of trying to manage a difficult woman, while ultimately making her perspective and agency central to the story.
Best for: the Shakespeare connection, adult romance, family interference, and Gabrielle Union’s commanding lead performance.
Smart heroines, literary adaptations, and social labels
5. Easy A (2010)
Easy A is a strong modern successor for viewers who like Kat’s intelligence, independence, and refusal to be defined by other people’s judgments. Emma Stone plays Olive, a high-school student whose invented story about losing her virginity becomes a rumor that reshapes her social identity.
The film draws on Nathaniel Hawthorne’s The Scarlet Letter and uses reputation, sexual rumor, and public labeling as comic material. Its heroine is more openly self-aware than Kat, and its writing is sharper and more contemporary, but both movies understand how quickly a teenager can become a character in somebody else’s story.
Best for: outspoken female leads, literary reworkings, reputation politics, and a more self-conscious teen comedy.
Rank #2
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6. She’s the Man (2006)
Another Shakespeare modernization, She’s the Man turns Twelfth Night into a broad high-school farce. Amanda Bynes plays Viola, who disguises herself as her twin brother to join a boys’ soccer team after her own team is cut. The resulting mistaken identities, gender performance, and romantic confusion create a much sillier film than 10 Things I Hate About You.
It lacks Kat and Patrick’s emotional restraint, but it shares the pleasure of translating Shakespearean complications into teenage social rules. The sports setting also gives it a different version of the outsider-versus-institution conflict.
Best for: Shakespeare, mistaken identity, physical comedy, gender-role reversals, and fast-moving romantic confusion.
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The DUFF updates the high-school-label premise for an era of social branding. Bianca discovers that her peers have categorized her as the “Designated Ugly Fat Friend,” a role supposedly defined in relation to her more conventionally popular friends. She then tries to reclaim control over the way she is seen.
Its themes of labels, self-acceptance, social hierarchy, and identity make it a natural recommendation for fans of Bianca and Kat’s storylines. The language around social status is more contemporary, although the film’s makeover and popularity conventions can still feel familiar.
Best for: social labels, self-definition, friendship, and a heroine pushing back against a role assigned by her peers.
8. To All the Boys I’ve Loved Before (2018)
This is the warmer and sweeter modern alternative. Based on Jenny Han’s book series, it follows Lara Jean after private love letters are accidentally sent to the boys who inspired them. A fake relationship becomes the basis for romantic wish fulfillment, emotional honesty, and family-centered coming of age.
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Best for: fake dating, family relationships, sweetness, and a contemporary teen-rom-com with an emotionally accessible lead.
9. Booksmart (2019)
Booksmart is not a direct romantic substitute, because its central relationship is the friendship between two academically successful seniors. It is nevertheless an excellent tonal match for anyone who remembers the friendship, jokes, music, and high-school anxiety of 10 Things I Hate About You more strongly than its central romance.
On the night before graduation, Amy and Molly try to experience all the fun they believe they missed while concentrating on school. The result is a chaotic, music-driven journey in which both confront the limits of their carefully managed identities.
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Rank #3
1990s and 2000s nostalgia matches
10. Can’t Hardly Wait (1998)
This graduation-party ensemble captures the heightened emotions and social types of late-1990s teen cinema. Multiple students arrive with different romantic hopes, resentments, and ideas about who they are supposed to become after high school ends.
It is less focused than 10 Things I Hate About You, since it follows an ensemble rather than one primary couple. Its music-driven nostalgia, romantic uncertainty, and sense that one night could change everything make it a strong companion watch.
Best for: graduation, party chaos, many intertwined romances, and the feeling of an entire high-school era ending.
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11. Dazed and Confused (1993)
Richard Linklater’s film is a loose, observational ensemble set on the last day of school in 1976. It contains much less conventional romance than 10 Things I Hate About You, but it shares an interest in cliques, rebellion, adolescent performance, social pressure, and the uncertainty of moving into the next stage of life.
The soundtrack and period atmosphere are central to its appeal. Watch it when you want to spend time inside a teenage social world rather than follow a tightly constructed romantic plot.
Best for: slice-of-life high-school atmosphere, memorable music, teenage identity, and a relaxed ensemble structure.
12. Empire Records (1995)
If the music, alternative identity, and ensemble camaraderie matter more to you than the romance, Empire Records is the choice. Over one day, a group of record-store employees tries to save its workplace while navigating crushes, insecurity, friendship, and the fear of being absorbed into a more conventional adult world.
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It does not reproduce the Shakespearean plot or the central romance of 10 Things, but its music-conscious, anti-establishment teen energy is closely related to the world Kat inhabits. It is also a natural pick for viewers who associate the 1999 film with its soundtrack as much as with its dialogue.
Best for: alternative youth culture, record-store nostalgia, ensemble friendship, and music-centered coming of age.
13. Never Been Kissed (1999)
Drew Barrymore plays a journalist who goes undercover as a high-school student and gets an unexpected second chance at adolescence after being bullied when she was younger. The film shares the period’s polished teen-comedy atmosphere and its interest in belonging, popularity, and romantic acceptance.
Its adult-undercover premise creates a very different dynamic from 10 Things I Hate About You, and some of its romantic framing is dated. It works best as a nostalgic 1990s companion rather than a direct thematic equivalent.
Best for: second chances, school belonging, 1990s teen-movie style, and a more sentimental romance.
Rank #4
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14. Pretty in Pink (1986)
For a more emotionally earnest outsider romance, try John Hughes’s Pretty in Pink. Molly Ringwald plays Andie, a working-class high-school student navigating class anxiety, friendship, fashion, and an attraction to a wealthier boy.
Andie is more vulnerable and less confrontational than Kat, so this is better understood as a companion to Bianca’s romantic storyline than as a replacement for Kat’s rebellious one. Its attention to class, social exclusion, clothing, and friendship makes it an important ancestor of later teen romances.
Best for: outsider identity, class tension, fashion, friendship, and an emotionally direct high-school romance.
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This is the least direct genre match, but it is an excellent Heath Ledger companion watch. Ledger plays William Thatcher, a determined outsider who enters the world of medieval jousting while trying to rise above his social position and pursue romance.
The film gives him the same broad charm, rebellious warmth, and playful confidence that made Patrick Verona memorable. Its anachronistic music, comedy, romance, and outsider narrative also make it a particularly satisfying follow-up for viewers who are watching because of Ledger rather than because they need another high-school story.
Best for: Heath Ledger, romantic charm, outsider ambition, comedy, and anachronistic music.
Darker, sharper, or less romance-centered alternatives
16. The Edge of Seventeen (2016)
The Edge of Seventeen is the emotionally rawest recommendation here. Hailee Steinfeld plays Nadine, an anxious and cynical high-school junior whose already difficult relationship with her mother becomes more volatile when her best friend begins dating her older brother.
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Nadine shares Kat’s defensive wit, outsider posture, and resistance to easy emotional explanations. The difference is that this film focuses more heavily on loneliness, friendship, family conflict, and emotional volatility than on a traditional romantic payoff.
Best for: caustic humor, complicated friendship, family tension, isolation, and a more psychologically direct coming-of-age story.
17. Ghost World (2001)
For viewers who connected most with Kat’s alienation and refusal to perform normal teenage popularity, Ghost World offers a darker and stranger alternative. Based on Daniel Clowes’s graphic novel, it follows two outsiders whose prankish encounter with an older record collector develops into an unexpected intervention in his romantic life.
It is drier, more uncomfortable, and more bittersweet than 10 Things I Hate About You. The friendship at its center is as important as any romance, and its characters are less interested in becoming socially acceptable than in figuring out whether their shared outsider identity can last.
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18. Drop Dead Gorgeous (1999)
Drop Dead Gorgeous is the most caustic recommendation on the list. Its mockumentary-style beauty-pageant competition follows ambitious young women navigating small-town expectations, family pressure, social performance, and increasingly dark events.
It shares the late-1990s teen-cultural atmosphere, ensemble comedy, and interest in young women competing against restrictive expectations. However, its murder plot and savage tone make it much darker than 10 Things I Hate About You. Treat it as an adjacent recommendation, not a like-for-like romantic comedy.
Best for: dark humor, beauty-pageant satire, ambitious young women, and a sharper take on competition and social performance.
How to choose your next movie
| If you liked this part of 10 Things… | Watch this first | Why |
|---|---|---|
| Kat’s sharpness and independence | Easy A | Another outspoken heroine resisting a public label. |
| The Shakespearean structure | Deliver Us from Eva | Another adaptation of The Taming of the Shrew. |
| High-school romance and popularity politics | She’s All That | A classic 1990s makeover-and-prom counterpart. |
| Fast dialogue and literary comedy | Clueless | A witty modernization of Emma. |
| Fake dating and romantic scheming | Drive Me Crazy | The pretend relationship is the central engine. |
| Music and 1990s atmosphere | Empire Records | An ensemble built around alternative youth culture and a record store. |
| Friendship and one-night chaos | Booksmart | A contemporary, music-driven high-school adventure. |
| Heath Ledger’s charm | A Knight’s Tale | Ledger plays another rebellious, warm-hearted outsider. |
| Kat’s alienation | Ghost World | A darker story about refusing conventional teenage performance. |
What to know before watching
10 Things I Hate About You is rated PG-13 and includes sexual references, teen drinking and smoking, crude language, and sex-related humor. The recommendations above do not all share the same age suitability or content profile. Older films may contain dated attitudes or romantic framing; Ghost World and Drop Dead Gorgeous are substantially darker; and Booksmart and The Edge of Seventeen approach teenage sexuality, anxiety, and emotional distress differently.
Streaming, rental, and digital-purchase availability changes by country, platform, and date. Check current listings in your region rather than relying on a static “where to watch” claim. Readers who prefer permanent access may want to compare formats for 10 Things I Hate About You DVD or Blu-ray, but edition, price, and stock should be checked before purchase.
The literary thread behind the recommendations
Part of 10 Things I Hate About You‘s staying power comes from how naturally it disguises Shakespeare’s The Taming of the Shrew inside a high-school romance. The film does not simply transfer the original plot to a new setting; it uses the source material to create tension around gender, control, reputation, and the question of whether a supposedly difficult woman must be changed before she can be loved.
That makes Deliver Us from Eva the closest structural follow-up. Clueless, She’s All That, Easy A, and She’s the Man extend the same tradition of using classic stories as frameworks for modern teen comedy. They are not interchangeable adaptations, and their approaches to gender and social identity differ, but they reward viewers who enjoy noticing the older story underneath the contemporary one.
Frequently Asked Questions
What is the movie most similar to 10 Things I Hate About You?
She’s All That is the closest overall match for late-1990s high-school romance, popularity politics, prom stakes, and a makeover premise. Deliver Us from Eva is the closest structural match because it is also based on The Taming of the Shrew.
Which movies like 10 Things I Hate About You have strong female leads?
Clueless, Easy A, She’s the Man, The DUFF, Booksmart, and The Edge of Seventeen all center memorable young women, although their tones range from light romantic comedy to emotionally raw coming-of-age drama.
Is Booksmart a romance like 10 Things I Hate About You?
Not primarily. Booksmart is centered on female friendship and a chaotic night before graduation. It is recommended for the high-school setting, quick humor, soundtrack, and coming-of-age energy rather than as a direct romantic equivalent.
Are all 18 recommendations suitable for the same age group?
No. The films vary in rating, content, tone, and dated attitudes. The original is PG-13 and includes sexual references, teen drinking and smoking, crude language, and sex-related humor. Ghost World and Drop Dead Gorgeous are darker than the central recommendations, while older films such as She’s All That and Never Been Kissed may reflect period-specific ideas about beauty and romance.
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The Bottom Line
For the most similar double feature, choose She’s All That or Clueless. For the Shakespeare connection, watch Deliver Us from Eva or She’s the Man. For Kat’s wit and outsider energy, try Easy A, The Edge of Seventeen, or—if you want something darker—Ghost World. And for the late-1990s soundtrack-and-friendship feeling, Empire Records remains one of the best adjacent picks.
Quick Recap
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