The 10 Best Movies Like 10 Things I Hate About You

When "10 Things I Hate About You" was released in 1999, it featured a cast of swoon-worthy young stars. Joseph Gordon-Levitt (who wasn't sold on the movie at first), Heath Ledger, Julia Stiles, and Larisa Oleynik were the film's core four, but the supporting cast was rounded out by actors like Gabrielle Union, David Krumholtz, Andrew Keegan, and Allison Janney, and everyone delivers a fun performance. The contemporary movie is actually an adaptation of William Shakespeare's classic play "The Taming of the Shrew," setting the romantic comedy at a modern high school instead of the olden days. It's about a pretty girl named Bianca (Oleynik) who isn't allowed to date until her uptight older sister Kat (Stiles) is taken; as a result, Cameron (Gordon-Levitt) pays the rambunctious Patrick (Ledger) to woo Kat. Hijinks ensue.

If you're a fan of the classic teen comedy, but you're getting tired of rewatching Kat recite the titular poem, there are plenty of other films that may scratch a similar itch. "10 Things I Hate About You" was part of a wave of 90s/00s Shakespearean adaptations that attempted to tell classic stories in new settings, so there are lots more to explore. Or maybe it's the film's young stars that bring you back time and time again; after all, who can resist a heartthrob like Ledger? 

Read on for some recommendations for where to go next, with our 10 best movies like "10 Things I Hate About You."

"She's All That," which came out the same year as "10 Things I Hate About You," is another attempt to adapt a classic play for teenagers. This one wasn't Shakespeare, but it's a loose adaptation of George Bernard Shaw's "Pygmalion," itself famously adapted as "My Fair Lady." In other words, not unlike "10 Things," the 1999 teenage romantic comedy "She's All That" is all about makeovers and an attempt to teach someone how to behave in a way that gains them acceptance in a specific social class. It's perfect high school fodder.

Freddie Prinze Jr. plays Zack, a cool kid late in his senior year who can't believe it when his girlfriend Taylor (Jodi Lyn O'Keefe) leaves him for Brock (Matthew Lillard), one of the stars of "The Real World." Not wanting to go to prom alone, Zack bets his friends (Dulé Hill and Paul Walker) that he'll be able to turn geeky outcast Laney Boggs (Rachael Leigh Cook) into a popular girl in time for the dance. As in "10 Things," to no one's surprise, he actually falls for the girl.

The cast is a who's-who of 90s-famous folks, many of whom are even more famous now. You'll spot "10 Things" star Gabrielle Union, Anna Paquin, and Kieran Culkin in supporting roles, and there are cameos by Lil Kim and Usher, not to mention Milo Ventimiglia playing a soccer player with no lines. Even Prinze's now-wife (and frequent co-star) Sarah Michelle Gellar shows up briefly. It's a treat.

One of the things that makes "10 Things I Hate About You" work is Heath Ledger's undeniable charisma. Even though he's playing a rogue — a character who's lying to the girl he's supposedly in love with in a way that's guaranteed to hurt her when she finds out — you can't help but love watching him. He's just that much of a heartthrob, an irresistible bundle of energy and magnetism.

For another heaping dose of Ledger's charm, check out his ridiculous (and ridiculously-fun) film "A Knight's Tale." Like many other films on this list, it's a very loose adaptation of some very old source material. In this case, the plot of the film sort of resembles the tale told by the knight in Geoffrey Chaucer's "Canterbury Tales." Writer-director Brian Helgeland's movie finds Ledger playing William Thatcher, a peasant who's always wanted to be a knight. When he hears of a jousting tournament, the winsome rascal goes undercover as Sir Ulrich von Liechtenstein of Gelderland, a knight who wants to compete.

"A Knight's Tale" is deliberately anachronistic, including songs like Queen's "We Are The Champions" and Thin Lizzy's "The Boys Are Back In Town." The anachronisms worm their way into the world of the story, too, including one suit of armor that sports a big Nike swoosh. It's a delightfully silly way to immerse modern audiences in the movie's medieval world, and it totally works, all thanks to Ledger's indisputable appeal.

Two years after she starred in "10 Things I Hate About You," Julia Stiles starred in yet another film that transposed a Shakespearean classic onto an American high school setting. "O" is an adaptation of "Othello," the Bard's iconic play about a Black man dealing with a dangerous, double-crossing, fake friend –0 a perfect story to tell with teenagers. Unlike "10 Things I Hate About You," though, this one isn't a comedy. "Othello" is one of the tragedies, and as such, "O" is a rather dark film about rage and resentment.

In "O," Othello is actually Odin (Mekhi Pfifer). He's a star basketball player who's dating a girl named Desi (Stiles), an update of Shakespeare's Desdemona. This enrages his best friend Hugo (Josh Hartnett), the film's version of the duplicitous, villainous Iago, and Hugo sets out to destroy Odin's relationship.

There have been numerous cinematic attempts to turn Shakespeare into something fun and lighthearted for teenagers, so "O" deserves credit for playing it straight. The movie sometimes tips over into melodrama, but that's not necessarily a bad thing; teenagers deserve the respect of having their romantic foibles and friendships taken seriously, which "O" does well. It's also an interesting examination of the racial politics of American high schools at the turn of the 21st century. The film came out on August 31, 2001, and we soon had other things on our mind for a while, but watching "O" is to revisit a time just before the world would change.

1999 was a good year to be a teenager at the movies. In addition to "10 Things I Hate About You," that year brought us "Never Been Kissed," another comedic dissection of the sexual politics of high school students. Drew Barrymore stars as Josie Gellar, a virginal twentysomething reporter who's ordered to go back to high school to report on what teenagers are like these days. She was a nerd, but she's determined to reinvent herself as a popular girl this time around. At least, she's desperate not to let the kids find out bullies used to call her "Josie Grossie."

"Never Been Kissed" isn't directly based on anything, but there are still numerous Shakespearean allusions. After all, The Bard loved mistaken-identity stories and wrote numerous plays where people went undercover. This film is an over-the-top, silly experience, but thanks to Barrymore's committed, lovable performance, it's ultimately a sweet film that's both hilarious and heartwarming. At the peak of her powers, no one did this kind of romcom better than Barrymore; we as a culture lost something when she retreated to daytime television.

Great as she is, Barrymore is helped along by a solid supporting cast, too. David Arquette (who was once on track to resurrect Bozo the Clown) plays her brother, a cool guy who also winds up re-enrolling at school to boost her popularity. You'll also spot Jessica Alba as a popular girl, John C. Reilly as Josie's editor, James Franco as one of the students, and even Octavia Spencer as a fellow newspaper employee.

This may be controversial, but for my money, the best of all the teenage Shakespeare adaptations is the 2006 film "She's the Man." Based on Shakespeare's "Twelfth Night," the film follows a spunky girl named Viola (Amanda Bynes) who takes her soccer-playing brother Sebastian's place at boarding school. Unfortunately, for her romantic prospects, Viola-as-Sebastian falls in love with his hunky roommate Duke Orsino (Channing Tatum). Shenanigans, of course, ensue.

There are lots of classic comedies where men go undercover as women. Jack Lemmon and Tony Curtis did it in "Some Like It Hot," for example, and the Wayans Brothers did it in "White Chicks." Less common are films where women go undercover as men, but Bynes finds just as many laughs in this material as those men did in theirs. She's the most gifted comedian of her generation, and it's all on full display in "She's The Man" — from her physical pratfalls to her wide-eyed, unexpected line readings, Bynes is a force of nature you can't look away from.

The movie is also queer-positive in a way that feels quietly radical for something made in the aughts, which were peak "no homo" years. Duke and Viola fully fall in love while he thinks she's a man, and while it is played for laughs, they're loving laughs that leave open the possibility that Duke's just gonna have to give in and go for it. If only!

Italian director Franco Zeffirelli helmed several Shakespearean adaptations, including the 1968 version of "Romeo and Juliet" that you might've watched in English class and the 1990 version of "Hamlet" that starred Mel Gibson and Glenn Close. Those are both good films, but the most-fun of his adaptations is "The Taming of the Shrew," a 1967 film starring real-life Hollywood power couple Elizabeth Taylor and Richard Burton. Taylor plays Kate — the Julia Stiles part from "10 Things I Hate About You" — while Burton interprets Petruchio, whom Heath Ledger brought to life as Patrick. If you're looking to see how the original play was done without, you know, seeing the play, then this version of "The Taming of the Shrew" is the best you can do.

Few people have ever been more famous than Taylor, so it's easy to write her off as all star power and little talent. The thing about Taylor, though, is that in addition to being one of the most compelling tabloid fixtures Hollywood has ever seen, she was also a tremendous actor. Her Kate is wild and unpredictable, a captivating whirlwind of a woman that makes Petruchio want to know her more the more she pushes him away. Burton, one of the silver screen's greatest thespians, matches her scene for scene; after all, at this point they had already starred together in several films, including the previous year's "Who's Afraid of Virginia Woolf?" Few real-life couples have ever been as engrossing on screen.

We can't discuss heartthrob-forward 1990s adaptations of Shakespeare without bringing up Baz Luhrmann's brilliant, batty "Romeo + Juliet." The film paired a pre-"Titanic" Leonardo DiCaprio with a post-"My So-Called Life" Claire Danes, making movie magic out of the classic story of star-crossed lovers. With over-the-top, eye-popping visuals and a soundtrack stuffed with chat hits like The Cardigans' "Lovefool" and Garbage's "#1 Crush," "Romeo + Juliet" influenced a whole generation of pop culture. 

You know the story: Romeo (DiCaprio) and Juliet (Danes) are teenagers from rival families, and they embark on a doomed relationship against the wishes of their parents. The story explodes into swoon-worthy romance and heart-stopping violence, helped along in this adaptation by transposing the story to modern-day California while keeping the iambic pentameter largely intact. Swords are traded for guns, making the original play's rivalry into something more like gang warfare; it's all an attempt to collapse time, much as Luhrmann later used hip-hop to stand in for jazz in his version of "The Great Gatsby."

This is the movie for anyone who thinks Shakespeare is boring. You can't be bored watching people like Paul Rudd, Harold Perrineau, Jesse Bradford, and John Leguizamo act out this material with all the excitement and verve of the best-looking music video you've ever seen. Shakespeare is timeless, folks! Also, for the record, the "Romeo + Juliet" set was full of as much drama as the film!

If you've enjoyed "10 Things I Hate About You" and are looking to understand the Julia Stiles phenomenon, then you have to check out "Save The Last Dance," from 2001. The movie regularly goes viral online for the clunky, embarrassing audition dance that forms the climax of the film – Stiles even recreated it on "Saturday Night Live" – but the movie as a whole is better than that oft-mocked clip suggests. Though her dancing skills leave much to be desired — especially for a movie about dance — Stiles is nevertheless a compelling lead.

In the 1990s and 2000s, we loved making movies where white people learn about the power of hip-hop dancing. A few years before "Step Up," there was "Save The Last Dance," a film about a ballet dancer named Sara (Stiles) who gives up dancing until she meets Derek (Sean Patrick Thomas). He teaches her to blend hip-hop with her ballet, and at the same time, she helps him study medicine in hopes of making it out of his dangerous neighborhood.

The movie's race relations are a little unwieldy, a little cliché, but they're reasonably well-intentioned. If nothing else, watching this and "O" together would be an intriguing case study in how Stiles was constructed, for a time, as an avatar of a certain kind of white womanhood. "Save the Last Dance" also boasts a great performance from Bianca Lawson and an early one from Kerry Washington, so it's worth watching for that reason alone.

Follow me here: "10 Things I Hate About You" star Julia Stiles went on to star in "O" with Josh Hartnett. A few months after that movie was released, Hartnett led the cast of "40 Days and 40 Nights," a sex comedy with a tone closer to "10 Things" than it is to "O." After all, this one involves a bet, too. Hartnett plays a sex addict named Matt, the kind of guy who goes from girl to girl, night after night, without a care in the world. After some performance issues caused by the fact that he's still in love with an ex, Matt swears he's going to give up sex for Lent. If he can do it, he'll be going without physical intimacy — including self-gratification — for the titular 40 days and 40 nights. His coworkers, including his roommate, start a betting pool, convinced he won't be able to complete his vow.

Of course, the newly-celibate Matt quickly meets a cute girl named Erica (Shannyn Sossamon, who was in "A Knight's Tale" with "10 Things" star Heath Ledger ... it's all connected!). As they fall for one another, he has to figure out how to put off having sex with her, desperate to prove he's able to abstain so that his coworkers don't win their bets against him.

If it were made today, this movie would likely be called "problematic." It certainly is, but that's also what makes it such a fun time capsule.

In "10 Things I Hate About You," Gabrielle Union plays Chastity, the best friend of Bianca (Larisa Oleynik). She'd just been in "She's All That" a few months earlier, but "10 Things" was filmed first, as she revealed on X, formerly Twitter, in 2024. "The 1st film I ever worked on. Such an amazing experience with the best cast," she wrote with a red heart emoji. "Can't believe it's been 25 years!"

By 2003, on the other side of "Bring It On," Union was a full-fledged star. That year, she led the cast of "Deliver Us From Eva," her second adaptation of "The Taming of the Shrew." This time, she played the Kat role, here named Eva. (It's a loose adaptation.) Eva is an annoyingly-smug career woman who bothers the men who are dating her friends; she's so annoying that they consider Eva to be full-on evil. "Eva's sister gave her a cross with Jesus on it for her birthday," one says. "The next day, Jesus was gone!" In an effort to get her out of their hair, they pay a playboy named Ray (LL Cool J) to date her, hoping he'll be able to soften her up. Do you think they fall in love?

Much like "10 Things" set the story at a high school, "Deliver Us From Eva" plants these archetypes firmly in the Black community. In other words, it's a great example of the adaptability and malleability of Shakespeare.