18 Movies to Watch If You Love “10 Things I Hate About You”

For another ’90s teen classic where a guy is way too pressed to get a girl who quite frankly enjoys her own company, there’s “She’s All That.” Popular jock Zack Siler (Freddie Prinze Jr.) has to turn outcast artist Laney Boggs (Rachael Leigh Cook) into prom queen material to win a bet and protect his reputation. For the record, because apparently it needs to be said: Laney was beautiful with her glasses! While we don’t exactly buy into the makeover trope that riddles teen movies of yesteryear, there’s still a lot to enjoy in this classic, like “10 Things I Hate About You“‘s Union, who steals every scene she’s in.

Like “10 Things I Hate About You,” “Clueless” adapts classic literature to a modern setting. This time, it’s Jane Austen’s “Emma.” If you’re, like, totally buggin’ and have yet to see the movie, “Clueless” is about a rich, popular, and seemingly shallow Beverly Hills high schooler, Cher, who takes newcomer and tomboy Tai under her wing. Give it a watch and you’ll be adding “as if!” into your everyday vocabulary in no time. And the nostalgic ’90s outfit inspiration has never been stronger.

If you’re looking for another Shakespeare adaptation, look no further than “Romeo + Juliet,” starring ’90s teen heartthrob Leonardo DiCaprio and Claire Danes as the star-crossed lovers. The film updates the tragedy’s setting to a modern Verona Beach while keeping the bard’s original dialogue. From director Baz Luhrmann, who also directed “Moulin Rouge!” and “Elvis,” you can expect a dynamic, dazzlingly colorful, energy-filled reimagination of a timeless classic – and some great onscreen kisses.

If you love “10 Things I Hate About You” because you’re a Stiles stan, then you have to watch “Save the Last Dance.” In the movie, Stiles is ballet dancer Sara, who moves to the south side of Chicago with her father after her mother dies. At her new school, she meets Derek (Sean Patrick Thomas), a talented hip-hop dancer who teaches her new moves and inspires her to chase her dreams. As Derek and Sara get close, their connection goes beyond the dance floor, and romance brews between the two. The movie also stars a young Kerry Washington.

Like “10 Things I Hate About You,” “Deliver Us From Eva” is an adaptation of Shakespeare’s “The Taming of the Shrew.” But this time, Union is front and center as Eva, a type A health inspector who rides hard for her sisters. Unfortunately, her sisters’ significant others can’t get what they want in their relationships on account of Eva’s constant interference and the fact that her sisters defer to her advice. So, the men conspire to pay player Ray Adams (LL Cool J) to woo Eva and distract her from her sisters’ love lives. The talented cast also includes Meagan Good and Essence Atkins.

Ah, the movie that made the internet fantasize about Noah Centineo spinning us around by the back pocket of our jeans. Based on Jenny Han’s novel, the Netflix film is about Lara Jean Covey (Lana Condor), a hopeless romantic who gets into a bind when her sister mails her secret love letters to all of Lara Jean’s past crushes, including Peter Kavinsky (Centineo). When Lara Jean and Peter enter an agreement to pretend to date, they start to catch real feelings. If there’s one thing to learn from “10 Things I Hate About You” and “To All The Boys,” it’s that little sisters can either wreak havoc or do wonders for a big sister’s love life.

In “10 Things I Hate About You,” one of the things that makes Kat such a cool, contemporary, feminist character is her unwillingness to compromise on her dream of going to college, boyfriend or not. If you ever wondered what it might be like to see her out of Padua and past high school, watch “Down to You.” It’s love at first sight for college students Imogen (Stiles) and Al (Prinze), but outside forces threaten to get in the way of their love reaching its full potential.

For another women-led film (Karen McCullah and Kirsten Smith wrote “10 Things I Hate About You“), watch Greta Gerwig‘s Oscar-nominated coming-of-age drama “Lady Bird.” The film stars Saoirse Ronan as strong-willed and deeply opinionated teenager Christine in her senior year of high school. Over the course of the movie, Christine butts heads with her hardworking mother (Laurie Metcalf), joins the theater program with her bestie (Beanie Feldstein), and learns tough lessons about love and sex. Beyond its sincere, authentic storytelling, “Lady Bird” is also one of the films that put Timothée Chalamet on our radar. But we’ll definitely take Ledger’s Patrick Verona over Chalamet’s Kyle any day.

This teen comedy masterpiece is multi-hypenate Olivia Wilde‘s first feature film as a director. In “Booksmart,” Feldstein and Kaitlyn Dever star as Molly and Amy, two overachievers who have spent their time in high school entirely focused on getting into their dream colleges. When they find out the classmates they look down on for spending their time partying also got into their dream schools, they embark on a wild night, one last stand, to make up for lost time.

Just like “10 Things I Hate About You” delights viewers with its sprawling cast of soon-to-be stars, you’ll be pleasantly surprised with “Booksmart”‘s cast of familiar faces, including “Theater Camp” star Molly Gordon.

It’s no secret that a little white lie can get blown way out of proportion. In this adaption of the classic novel “The Scarlet Letter,” Emma Stone is a teenager who flips a scandalous rumor about her first time having sex into a financial and social opportunity – and it’s not what you think. Teen comedies are notorious for perpetuating sexist beliefs and ideas about women and virginity, but “Easy A” is an unexpectedly funny, empowering critique of society that reclaims women’s sexuality. In addition to Stone, the movie also has performances from Penn Badgley, Amanda Bynes, Stanley Tucci, and Lisa Kudrow.

Another coming-of-age film, “The Edge of Seventeen” is about how school junior Nadine’s (Hailee Steinfeld) world gets turned upside down when her all-star brother starts dating her best friend not long after her dad dies. All of a sudden, Nadine feels alone in the world, with a mother who doesn’t understand her, her seemingly perfect brother, and a bestie who’s making new friends. With the guidance of her teacher Mr. Bruner (Woody Harrelson), who delivers his advice with a side of sarcasm and dark humor to match Nadine’s drama and angst, Nadine gets through the ups and downs of an awkward adolescence and the challenges of high school.

This is no longer a hot take, but can we all agree the East Compton Clovers are way better than the Toros? They deserved their win in the final competition. “Bring It On” is a teen cheerleading competition film, starring Kirsten Dunst and the incomparable teen movie queen Union. Though it may seem somewhat superficial on the surface, this iconic comedy flick with its flips, cheers, and choreo is actually pretty deep in hindsight. It’s not just about overcoming adversity and winning competitions. Whether intended or not, it’s also a commentary on racial disparities, stereotypes, and cultural appropriation.

This Netflix coming-of-age dramedy is one of many modern stories that riffs on the play “Cyrano de Bergerac.” To put it simply, it’s essentially a story where one person speaks through another person to woo a love interest. In “The Half of It,” football player Paul Munsky pays Ellie Chu to write love letters to his crush, Aster Flores. Ellie can help her father pay the bills and Paul gets the girl, or so you think. In the process, Ellie actually befriends Paul and falls for Aster. Meanwhile, thinking Paul’s words are his own, Aster’s actually catching feelings for Ellie. Now, that’s a love triangle!

If “10 Things I Hate About You” left you wanting to see more Ledger, watch “A Knight’s Tale” next. The actor plays a squire posing as a knight and trying to win the affection of a fair maiden in medieval Europe. And jousting is the way to do it. This movie definitely gives medieval fairy-tale vibes with its court dancing, tournaments, castles, and candlelit kisses. Plus, Ledger’s wink and smirk are enough to make us swoon.

“Bottoms,” released in August 2023, is about two teenage lesbians who start a fight club to woo the cheerleaders they have crushes on. Like “10 Things I Hate About You,” it’s very funny and weird, and it’s able to critique the weird high school power struggles that can make your teen years so terrible. Ayo Edebiri‘s Josie and Rachel Sennott‘s PJ stand in a line of teen movies that you can trace right back to “10 Things.”

In the Paramount+ film “Honor Society,” Angourie Rice stars as Honor, who’s bent on getting into Harvard by any means necessary. Convinced only one kid from her school will get in, she schemes to sabotage the others she sees as rivals – especially loner Michael (Gaten Matarazzo). But things twist and turn in ways Honor (and the audience) don’t expect, and you won’t see the (hilariously great) ending coming.

“Do Revenge,” which premiered on Netflix in 2022, stars Camila Mendes and Maya Hawke as two teens who team up to get revenge on high school classmates who’ve wronged them. It serves up teen comedy hijinks (and romance) and lampoons the indignities of high school life. It also features a completely amazing cameo from “Game of Thrones” star Sophie Turner.

Netflix’s “Moxie,” inspired by 1990s riot grrrl culture, is about a group of teen girls who decide to fight back against the sexist jerks at their high school. They don’t literally watch “10 Things I Hate About You,” but it feels like their actions would definitely be Kat Stratford-approved.