Are you a fan of witty banter, high school hijinks, and swoon-worthy romance? If you’ve watched “10 Things I Hate About You” more times than you can count, you’re in luck! We’ve compiled a list of the 20 best movies like “10 Things I Hate About You” that will satisfy your craving for smart, funny, and heartfelt teen comedies.
From ’90s classics to modern gems, these films capture the same spirit of irreverent humor, sharp dialogue, and unexpected romance that made “10 Things I Hate About You” a beloved favorite. Whether you’re looking for Shakespearean-inspired plots, fake dating schemes, or coming-of-age stories with a twist, our curated selection has something for every teen movie enthusiast.
So grab some popcorn, settle in, and get ready to discover your next favorite high school rom-com. From “Clueless” to “The Edge of Seventeen,” these 20 movies will make you laugh, cry, and fall in love all over again. Let’s dive into the world of unforgettable teen cinema!
1. Clueless (1995)
Clueless is a classic ’90s teen comedy that, like 10 Things I Hate About You, is loosely based on a classic work of literature. While 10 Things takes inspiration from Shakespeare’s The Taming of the Shrew, Clueless is a modern retelling of Jane Austen’s Emma.
The movie follows popular and wealthy high school student Cher (Alicia Silverstone) as she plays matchmaker for her teachers and gives a fashion-challenged new student named Tai (Brittany Murphy) a makeover. Along the way, Cher navigates the ups and downs of teenage romance and friendship. With its clever writing, memorable characters, and iconic ’90s fashion, Clueless is a witty and charming teen flick in the same vein as 10 Things I Hate About You.
2. She’s All That (1999)
She’s All That puts a ’90s spin on the classic Pygmalion story. Popular jock Zack (Freddie Prinze Jr.) makes a bet with his friends that he can turn artsy outcast Laney Boggs (Rachael Leigh Cook) into the prom queen.
As Zack helps Laney get a new look and come out of her shell, the two start to develop real feelings for each other. But Laney eventually finds out about the bet, putting their budding romance in jeopardy. She’s All That may follow a predictable formula, but it’s elevated by the charming lead performances and chemistry between Prinze and Cook. If you enjoy the “popular guy falls for misfit girl” dynamic of 10 Things, check this one out.
3. Easy A (2010)
While Easy A came out over a decade after 10 Things I Hate About You, it has a similar irreverent sense of humor and literary inspiration. Loosely based on Nathaniel Hawthorne’s The Scarlet Letter, the film stars Emma Stone as Olive, a clean-cut high school student who lies about losing her virginity to impress her best friend.
When gossip about Olive’s (made-up) promiscuity starts to spread around school, she decides to lean into her new “bad girl” persona. Olive even starts wearing a red “A” (for adulterer) on her clothes, an homage to The Scarlet Letter. Stone’s star-making performance drives this smart and snarky teen comedy that both celebrates and satirizes high school stereotypes and rumor mills.
4. Can’t Hardly Wait (1998)
Set at a wild graduation party, Can’t Hardly Wait follows a group of teens trying to make the most of their last night together before leaving high school behind. The ensemble cast includes Jennifer Love Hewitt, Ethan Embry, Charlie Korsmo, Lauren Ambrose, Seth Green and more ’90s teen movie faves.
Like 10 Things I Hate About You, much of the humor comes from the interactions between different high school cliques and archetypes – the jocks, the nerds, the popular girls, the outcasts. It’s a fun, nostalgic romp with a killer ’90s soundtrack.
5. Bring It On (2000)
This cheerleading comedy brings plenty of pep and biting humor. Bring It On stars Kirsten Dunst as Torrance, the newly elected captain of the Toros cheerleading squad. Torrance is horrified to learn that the Toros’ past championship routines were actually stolen from a rival squad.
Determined to lead her team to victory with original choreography, Torrance convinces bad boy Cliff (Jesse Bradford) to help her craft some new routines. Dunst and Gabrielle Union, as the captain of the rival squad, are a blast to watch as they trade barbs. Like 10 Things I Hate About You, Bring It On is endlessly quotable and doesn’t shy away from edgier jokes.
6. Never Been Kissed (1999)
In this charming rom-com, Drew Barrymore plays Josie, an insecure copy editor who gets the chance to go undercover and report on high school life for her newspaper. Posing as a student, the initially awkward Josie gets a second chance at the teenage experience she never had.
As Josie gains confidence and even starts falling for her English teacher (Michael Vartan), she risks getting her story at the expense of her new friendships. Barrymore is a delight in this sweet, funny film that lets you relive high school through an adult’s eyes. Never Been Kissed pairs well with 10 Things I Hate About You for a nostalgic double feature.
7. Cruel Intentions (1999)
For a darker, more scandalous take on teen romance, try Cruel Intentions. Based on the French novel Les Liaisons dangereuses, the movie centers on a pair of manipulative step-siblings, Sebastian (Ryan Phillippe) and Kathryn (Sarah Michelle Gellar), who make a twisted bet involving the virginal Annette (Reese Witherspoon).
Things get even more complicated when Sebastian starts to develop real feelings for Annette. With its attractive cast and soapy plot, Cruel Intentions was a big hit with teen audiences. It may be more risque and dramatic than 10 Things I Hate About You, but it’s just as entertaining and quotable.
8. Drive Me Crazy (1999)
Melissa Joan Hart and Adrian Grenier star as Nicole and Chase, two mismatched neighbors who start fake-dating each other to impress their respective crushes. But in classic rom-com fashion, Nicole and Chase catch real feelings along the way.
Drive Me Crazy is a cute, lightweight comedy anchored by the appealing lead performances. Hart is particularly fun as an uptight overachiever who learns to loosen up. For more fake relationship hijinks with a dash of Shakespeare, pair this with 10 Things I Hate About You.
9. Saved! (2004)
This satirical comedy takes aim at religious hypocrisy and intolerance. Saved! follows a group of teens at a Christian high school, including devout good girl Mary (Jena Malone). When Mary’s boyfriend confesses that he’s gay, she decides to sacrifice her virginity to “cure” him.
After ending up pregnant, Mary starts to question her faith and falls in with some other school outcasts. Saved! puts a subversive spin on the teen movie formula, with a sharp wit and stellar cast that also includes Mandy Moore and Macaulay Culkin. Like 10 Things I Hate About You, it has fun playing with character stereotypes.
10. The Edge of Seventeen (2016)
Hailee Steinfeld shines in this coming-of-age dramedy about an awkward teen named Nadine struggling to find her place. The Edge of Seventeen follows Nadine as she deals with the ups and downs of high school life, including her fraught relationship with her popular older brother.
Things get even more complicated when Nadine’s best friend starts dating her brother. Steinfeld brings humor and heart to the role, crafting a realistically messy and sympathetic portrait of teenage angst. With its mix of laughs and bittersweet moments, The Edge of Seventeen is perfect for fans of 10 Things I Hate About You.
11. To All the Boys I’ve Loved Before (2018)
Based on the popular YA novel, To All the Boys I’ve Loved Before is a sweet and heartfelt teen rom-com. Lara Jean (Lana Condor) is a shy romantic who pours out her feelings by writing secret love letters to her crushes, which she never intends to send.
But when the letters accidentally get mailed out, Lara Jean finds her love life spinning out of control. To convince her most recent crush that she’s over him, Lara Jean starts fake-dating another letter recipient, Peter Kavinsky (Noah Centineo). Naturally, real sparks soon start to fly between them. Condor and Centineo have adorable chemistry in this Netflix hit that, like 10 Things I Hate About You, offers a softer take on the teen movie genre.
12. Mean Girls (2004)
Written by Tina Fey, Mean Girls is an endlessly quotable and rewatchable teen comedy. Cady (Lindsay Lohan), a formerly homeschooled student, is the new girl trying to navigate the complex social hierarchy of her suburban high school. She infiltrates the Plastics, a popular clique led by queen bee Regina George (Rachel McAdams).
But as Cady schemes to overthrow Regina, she starts becoming just as two-faced and popularity-obsessed as the girls she initially judged. Mean Girls is a smart and scathing look at high school power dynamics, cliques and the pressure to fit in. It’s a new classic that pairs perfectly with 10 Things I Hate About You.
13. The DUFF (2015)
In this modern update of the teen makeover movie, Bianca (Mae Whitman) is horrified to learn that she’s seen as the DUFF (Designated Ugly Fat Friend) of her more popular pals. Determined to shake the label, Bianca enlists the help of her jock neighbor Wesley (Robbie Amell) to give her a social overhaul.
The DUFF hits a lot of the expected beats, but Whitman’s charming performance keeps it feeling fresh. As Bianca learns to embrace her individuality, the film offers a sweet message about staying true to yourself. The DUFF should satisfy anyone looking for a 10 Things I Hate About You-style high school comedy with heart.
14. Booksmart (2019)
On the eve of graduation, studious best friends Amy (Kaitlyn Dever) and Molly (Beanie Feldstein) decide to finally let loose and attend a big party with their classmates. The only problem? They don’t know the address. Booksmart follows the girls’ hilarious odyssey to track down the party and cram four years of missed fun into one wild night.
Olivia Wilde’s directorial debut puts a fresh spin on the teen party comedy, anchored by Dever and Feldstein’s winning performances. Like 10 Things I Hate About You, Booksmart has a quick wit, a killer soundtrack and an ultimately uplifting message about friendship and being yourself.
15. The Half of It (2020)
Shy, introverted student Ellie (Leah Lewis) earns extra cash by writing essays for her classmates. When a sweet but inarticulate jock named Paul (Daniel Diemer) asks for help wooing his crush Aster (Alexxis Lemire), Ellie reluctantly agrees. The only problem? Ellie has feelings for Aster too.
The Half of It offers a queer spin on the classic Cyrano story, as Ellie helps Paul woo Aster through beautifully ghostwritten love letters. Writer-director Alice Wu crafts a poignant coming-of-age story that, like 10 Things I Hate About You, has its share of banter and bittersweet romance. But the film is ultimately more interested in Ellie’s journey of self-discovery than who gets the girl in the end.
16. Heathers (1989)
One of the darkest teen comedies ever made, Heathers follows Veronica (Winona Ryder), a popular girl who’s grown disenchanted with her ruthless clique of friends, all named Heather. When Veronica meets rebellious new student J.D. (Christian Slater), the two start bumping off their cruel classmates and staging the deaths as suicides.
With its pitch-black humor and biting social satire, Heathers is a far cry from the softer sensibility of 10 Things I Hate About You. But for anyone interested in a more scathing and subversive take on high school hierarchies, it’s essential viewing. Heathers paved the way for teen movies that aren’t afraid to go to dark and dangerous places.
17. Ferris Bueller’s Day Off (1986)
Okay, so this John Hughes classic isn’t a teen romance. But Ferris Bueller’s Day Off is still essential viewing for anyone who loves a good high school comedy about defying expectations and sticking it to authority.
When popular and charming Ferris (Matthew Broderick) decides to skip school and spend a day gallivanting around Chicago, he drags his neurotic best friend and his bitter sister along for the ride. Ferris breaks the fourth wall to bring the audience in on his schemes, and the film takes some surreal and unexpected detours. It’s a fast, funny ode to living in the moment and challenging the status quo – a sentiment that 10 Things I Hate About You’s Kat Stratford would definitely get behind.
18. Say Anything… (1989)
Say Anything… is one of the definitive teen romantic comedies of the ’80s. John Cusack stars as lovable everyman Lloyd Dobler, who on a dare decides to ask out the beautiful class valedictorian Diane Court (Ione Skye) on a date. To everyone’s surprise, she says yes.
But their new relationship is tested when Diane’s disapproving father tries to keep them apart. Cusack and Skye have swoonworthy chemistry, and the film is full of iconic moments – like Lloyd blasting “In Your Eyes” on a boombox held over his head. With its sweet, unabashedly romantic sensibility, Say Anything… makes a perfect double feature with the snarky but equally heartfelt 10 Things I Hate About You.
19. Nick & Norah’s Infinite Playlist (2008)
This charming indie rom-com follows two music-obsessed teens over the course of one eventful night in New York City. Nick (Michael Cera) is a sensitive emo boy reeling from a bad breakup. Norah (Kat Dennings) is a sarcastic rich girl who convinces Nick to be her boyfriend for five minutes to prove a point to her judgmental friend.
Their fateful meeting kicks off a night of misadventures and musical discoveries as they search for a secret show from their favorite band. Nick & Norah’s Infinite Playlist is a funny and heartfelt ode to teen romance and the unifying power of a killer soundtrack. If you swooned at Heath Ledger serenading Julia Stiles on the bleachers in 10 Things I Hate About You, this is the movie for you.
20. 500 Days of Summer (2009)
500 Days of Summer (2009) is a unique romantic comedy-drama that explores the complexities of modern relationships through a nonlinear narrative. The film follows Tom Hansen (Joseph Gordon-Levitt) as he reflects on his failed relationship with Summer Finn (Zooey Deschanel), a woman who doesn’t believe in true love. The movie cleverly subverts rom-com tropes, focusing on the realities of love and heartbreak.
Like ‘10 Things I Hate About You‘, ‘500 Days of Summer’ is a refreshing take on the romantic comedy genre. Both films feature charming leads, witty dialogue, and a thoughtful exploration of young love. However, while ’10 Things I Hate About You’ is a more traditional rom-com with a happy ending, ‘500 Days of Summer’ offers a bittersweet and realistic look at relationships, emphasizing personal growth and the importance of moving forward after a breakup.
So there you have it – 20 movies to watch if you’re craving more of the sharp, heartfelt teen movie magic of 10 Things I Hate About You. Whether you’re in the mood for snarky satire, swoony romance or a little bit of both, these films deliver. They’ll make you laugh, make you cringe with recognition, and maybe even make you fall in love. Because in the end, there’s nothing quite like a great teen movie to capture all the joy, pain and humor of those tumultuous high school years. Happy watching!
