10 Romantic Comedies Movies Like 10 Things I Hate About You

A modern version of Shakespeare’s controversial comedy “The Taming of the Shrew” came out in 1999. More than 20 years later, Movies Like 10 Things I Hate About You is still a huge hit with high school comedians. In the movie, Cameron, a new student played by Joseph Gordon-Levitt, wants to go on a date with Bianca, a famous sophomore played by Larisa Oleynik. However, Bianca is more interested in senior Joey (Andrew Keegan), and their overprotective father won’t let her date until her older sister Kat (Julia Stiles) does. Cameron comes up with a plan: he gets bad boy Patrick (Heath Ledger) to like Kat, but only if he pays him a certain amount of money. Patrick also has his work cut out for him because Kat is against dating. Kat is a woman who has been burned by boys before. Patrick finally gets her to like him, and (gasp!) he starts to really like her.

There are many memorable scenes in the movie, such as when Kat dances on top of a table while drunk and when Patrick sings to Kat on the school bleachers as a romantic move. Once Patrick and Kat were making out in the paint, who wouldn’t want to go on a paintball date? And let’s not forget that famous punch Bianca throws at Joey.

Many young actors who went on to become stars are in the movie. Gabrielle Union, who was criminally overlooked in many teen movies in the 1990s and early 2000s, is one of them. And Allison Janney is famous for her role as a school counselor who writes sexy books in her free time. Many years later, “10 Things I Hate About You ” is still remembered for its strong, feminist female lead. However, it was made at a time when most teen romances were too white and straight.

Are you looking for another movie like “10 Things” that will make you laugh out loud? Here are 10 movies like 10 Things I Hate About You. They range from adaptations of classic books to teen comedies with a feminist bent to stars from the movie.

10 Movies Like 10 Things I Hate About You:

1.She’s All That

For another teen classic from the 1990s, watch “She’s All That.” In it, a guy tries way too hard to get a girl who just wants to be alone. To win a bet and keep his good name, popular jock Zack Siler (Freddie Prinze Jr.) has to make outcast artist Laney Boggs (Rachael Leigh Cook) look like a prom queen. Laney looked beautiful with her glasses, just in case it needs to be said again: We don’t really like the makeover trope that’s common in old teen movies, but there are still a lot of good things about this classic. For example, Union from “10 Things I Hate About You” steals every scene she’s in.

2. A Knight’s Tale

If you love Y2K Heath Ledger, put A Knight’s Tale on hold. In this action-comedy set in the Middle Ages, his character William Thatcher could beat Patrick Verona in a battle of the cutest. William leaves his life as a peasant behind when his master dies and pretends to be a knight to win jousting matches and the heart of the woman he loves (Shannyn Sossamon). Ledger has since played worse and more dramatic parts, but this one is still a cute and overlooked gem.

3. Clueless

Like “10 Things I Hate About You,” “Clueless” brings old stories into the present day. Her name is Jane Austen, and the book is “Emma.” You really should see “Clueless” if you haven’t already. It’s about a rich, popular, and seemingly shallow high school student in Beverly Hills named Cher who takes in a new girl named Tai and makes her her friend. After watching it, you’ll use “as if!” all the time. And the desire to wear clothes from the 1990s has never been stronger.

4. Booksmart

As 10 Things About You was for an age, Booksmart is an instant classic that not every teen comedy can be. This movie, directed by Olivia Wilde, has everything a great teen movie should have, from amazing needle drops to a memorable outfit. It also has jokes that will make you laugh out loud, and they come at a fast pace. It all starts when Amy (Kaitlyn Dever) and Molly (Beanie Feldstein), best friends since high school, decide to party like they did in high school all at once because they think they may have gone too far after only going to school for four years.

5. Romeo + Juliet

“Romeo + Juliet,” starring Leonardo DiCaprio as the lovelorn lovers and Claire Danes as the girl who falls in love with him in the 1990s, is another Shakespeare version you don’t need to look any further. The tragedy takes place in modern-day Verona Beach, but the movie sticks to the playwright’s original lines. Baz Luhrmann, who directed “Moulin Rouge!” and “Elvis,” has reimagined a timeless classic in a way that is lively, bright, and full of energy. There are also some great kisses on screen.

6. Can’t Hardly Wait

Some people don’t like Can’t Hardly Wait as much as other teen movies from the 1990s, but it will still take you to “Paradise City.” A lot of messing around and different “will they or won’t they” situations happen at one graduation party. Some stars from the time, like Jennifer Love Hewitt and Ethan Embry, round out the cast. There are also cameos by Selma Blair, Jason Segel, Clea DuVall, and other actors who were just starting to become famous.

7. Save the Last Dance

If you like “10 Things I Hate About You” because you like Stiles, you need to see “Save the Last Dance.” When Sara’s mother dies, she goes to the south side of Chicago with her father. Stiles plays Sara in the movie. She meets Derek (Sean Patrick Thomas), a skilled hip-hop dancer at her new school. He shows her new moves and encourages her to follow her dreams. Once Derek and Sara become close, their relationship goes beyond the dance floor, and love starts to grow between them. A young Kerry Washington also plays a part in the movie.

8. Dazed and Confused

Okay, okay, okay: There are a lot of reasons Fans of popular classics from the 1990s will remember Dazed and Confused. The intense feelings and social stresses of high school are shown in 10 Things I Hate About You. This Richard Linklater comedy about everyday life shows how careless it can feel. It takes place in Austin, Texas, on the last day of school in 1976 and follows a group of characters as they haze the new rookie class. There are a lot of stars in the cast, like Ben Affleck, Milla Jovovich, Matthew McConaughey, and Parker Posey. The music is also one of the best of all time.

9. Deliver Us From Eva

“Deliver Us From Eva” is based on Shakespeare’s “The Taming of the Shrew,” just like “10 Things I Hate About You.” But this time, Union is the star as Eva, a Type A health inspector who fights hard for her sisters. The boyfriends or girlfriends of her sisters can’t get what they want in relationships because Eva is always getting in the way and her sisters listen to her advice. The men then plan to pay player Ray Adams (LL Cool J) to flirt with Eva and take her mind off of the love lives of her sisters. Also in the talented group are Meagan Good and Essence Atkins.

10. Cruel Intentions

Cruel Intentions is also based on a work from the 1400s, though it is darker than 10 Things I Hate About You. It takes place in the high-class world of kids from Manhattan who grew up on the Upper East Side and spend the summers in the Hamptons. The teenage plans are a bit nastier than the Stratford sisters’ plan to find a way to get around not being able to date—as when sneaky queen bee Kathryn (Sarah Michelle Gellar) gets her playboy stepbrother Sebastian (Ryan Phillippe) to date good girl Annette (Reese Witherspoon) as a bet—but it’s still a great teen drama that many people felt a bit rebellious while watching it at sleepovers.

Conclusion:

Whether you’re in the mood for a witty modernized Shakespeare adaptation, a nostalgic ’90s rom-com, or a fresh feminist take on teen romance, these films offer the perfect mix of humor, heart, and high school drama. Movies Like 10 Things I Hate About You remains a beloved classic, and these 10 movies capture a similar charm—whether through their unforgettable characters, iconic romance, or sharp comedic timing. From Clueless’ fashion-forward satire to A Knight’s Tale’s medieval mischief, each of these films delivers a dose of nostalgia and feel-good entertainment.

So grab some popcorn, relive the era of mixtapes and teen angst, and dive into these romantic comedies that will make you laugh, swoon, and maybe even shed a tear. Which one will you watch first?

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