20 Hilarious Movies like 10 Things I Hate About You

10 Things I Hate About You is a classic 90s romantic comedy that’s one of the most rewatchable movies around.

But if you love the teen movie genre and have watched it over and over again, you probably fancy a change. This article will show you twenty movies similar to 10 Things I Hate About You.

Read through the list below and start working your way through each movie.

There are some golden nuggets in this one, so make sure you check them all out.

She’s All That

Release Date: 1999

This movie is a 1999 romantic comedy film that tells the story of a school student named Zack who makes a bet with his friends that he can turn a plain, unpopular girl named Laney into the school’s prom queen.

Zack initially sees the bet as a way to win back his cheerleader girlfriend, but as he gets to know Laney better, he begins to develop feelings for her.

Will this budding prom queen get a happy ending? Or will it end in tears?

The movie is similar to “10 Things I Hate About You” as it’s a romantic comedy set in a high school, and it explores themes of social hierarchy.

Both movies also feature characters who initially seem to be very different from each other but eventually fall in love.

She’s All That was a box office success and has become a classic teen movie within the romantic comedy genre.

Starring in the movie is Freddie Prinze Jr., Rachael Leigh Cook, Paul Walker, and Matthew Lillard.

The Duff

Release Date: 2015

The Duff is a 2015 teen comedy film that follows high school student Bianca Piper, who is nicknamed the “Designated Ugly Fat Friend” (DUFF) by other students.

After realising that she’s seen as the DUFF in her group of friends, Bianca sets out to prove to herself and others that she is more than just a DUFF.

The movie deals with themes of self-esteem, acceptance, and finding one’s place in the world, similar to 10 Things I Hate About You.

The Duff is a funny and heartwarming movie that tells a high school coming-of-age tale in a relatable and entertaining way.

The movie stars Mae Whitman, Robbie Amell, and Bella Thorne.

Never Been Kissed

Release Date: 1999

Never Been Kissed is a romantic comedy film released in 1999 and directed by Raja Gosnell.

The film stars Drew Barrymore as Josie Geller, a 25-year-old advice columnist who poses as a high school student to infiltrate the school’s inner circle and research a story for the Chicago Sun-Times.

However, while she tries to navigate her way around high school, Josie finds herself falling for her favorite teacher, Sam Coulson (played by Michael Vartan). But, as her publication deadline approaches, problems arise, and it’s only a matter of time before she has to make a difficult choice.

Meanwhile, she takes the opportunity to reconnect with her former best friend, Aldys (played by Leelee Sobieski).

As with many movies like 10 Things I Hate About You, Never Been Kissed is a “coming of age” movie set in high school. They may have different characters and storylines, but both films have the same feel to them.

Easy A

Release Date: 2010

Easy A is a 2010 comedy film that tells the story of a high school student named Olive (played by Emma Stone) who pretends to lose her virginity to gain popularity at school.

However, things become complicated when her lies start to spiral out of control, leaving Olive in a spot of bother with her parents, school teachers, and friends. Will Olive’s journey of self-discovery have a happy ending?

The film is similar to 10 Things I Hate About You in that both movies revolve around high school students and the challenges they face in their social lives.

Both movies also feature a protagonist who finds themselves in a situation where they need to pretend to be someone they’re not in order to fit in with their peers.

Easy A is one of the best movies in the teen comedy genre.

Starring alongside Emma Stone is Penn Badgley, Amanda Bynes, and Thomas Haden Church.

Mean Girls

Release Date: 2004

Mean Girls is a 2004 comedy film written by Tina Fey.

The movie follows Cady Heron, a teenage girl who moves to a new school in the USA after being home-schooled in Africa.

Cady is introduced to the school’s social hierarchy (which she’s never experienced before) and becomes friends with a group of popular students known as the “Plastics”.

At first, things are great; she’s popular, having fun, and has all the boys after her.

However, as she becomes more involved with the Plastics, Cady realises that they’re manipulative & cruel and starts to plot against them. But, she loses herself along the way, becoming like the girls she despises. High school life is pretty tough, isn’t it?

As far as teen movies go, this one has all the teen movie tropes you love.

In addition to Lindsay Lohan, Mean Girls stars Rachel McAdams, Amanda Seyfried, Lacey Chabert, and Tina Fey; each delivers great performances.

Watch this movie and let the high school drama commence.

It might not have five high school students like the classic from John Huges, the Breakfast Club, but it’s still awesome.

The Princess Diaries

Release Date: 2001

The Princess Diaries is a rom-com film about a teenage girl named Mia Thermopolis who discovers she’s actually the princess of a small European country called Genovia.

Mia is reluctant to accept her new royal duties, but with the help of her eccentric grandmother (the Queen of Genovia) and her best friend Lilly, she learns to embrace her new royal identity.

Oh, she does this while in high school and you thought your high school life was tough. Mia even falls for a charming jock, which could be good news or bad… but if you’ve seen similar movies, you’ll know she’ll have some challenges ahead.

The movie stars Anne Hathaway with Julie Andrews and is joined by Hector Elizondo and Mandy Moore.

Clueless

Release Date: 1995

Clueless is a 1995 teen comedy film about a wealthy and popular kid named Cher Horowitz (played by Alicia Silverstone).

She tries to use her social status and fashion sense to help a new student become popular and improve her social life. Meanwhile, she falls in love with a new student named Josh (played by Paul Rudd).

Alicia Silverstone is best known for her roles in Scooby-Doo 2: Monsters Unleashed, Senior Year, From Below, The Crush, Batman & Robin, and Last Survivors.

Paul Rudd is best known for Ant-Man, The Avengers: Endgame, I Love You Man, and Friends.

The pair are joined by Brittany Murphy, Stacey Dash, Donald Faison, and Breckin Meyer.

The movie has a similar light-hearted tone to it and a brilliant set of characters; if you enjoyed 10 Things I Hate About You, you’ll love this.

She’s the Man

Release Date: 2006

She’s The Man is a comedy film about a young woman named Viola who disguises herself as her twin brother so she can play football at his new boarding school (in the men’s team).

However, while her plan starts as a success, she soon falls for her teammate, roommate and high school hunk, Duke.

Meanwhile, her roommate Duke is confused about why he’s attracted to a guy, and the whole situation becomes confusing for them both. Will Viola reveal her hidden identity to Duke so they can date?

The film is similar to 10 Things I Hate About You as both movies involve a young woman disguising who she is while pursuing a romantic interest. It also highlights the expectations society has of young women.

This teen drama is a loosely based modern adaptation of William Shakespeare’s play “Twelfth Night”.

Starring alongside Amanda Bynes is Channing Tatum, James Kirk, Robert Hoffman, Laura Ramsey, and Vinnie Jones.

A Knight’s Tale

Release Date: 2001

A Knight’s Tale is about a young man named William who poses as a knight in medieval England in order to compete in jousting tournaments.

He’s joined by his friends, including his “squires” Roland and Wat, as they travel across England so William can compete in Tournaments to gain fame and fortune.

However, during one tournament, William falls in love with a noblewoman named Jocelyn and must navigate the nobility hierarchy and traditions in order to be with her.

The movie stars Heath Ledger, who’s one of the main characters in both this movie and 10 Things I Hate About You. A Knight’s Tale is by far one of my favourite Heath Ledger movies.

He’s joined by Mark Addy (Love Actually), Shannyn Sossamon (40 Days And 40 Nights), Paul Bettany (The Avengers: Age Of Ultron), and Rufus Sewell (The Holiday).

This movie is one of my favourites and will have you laughing from beginning to end. It also has some great action scenes.

Roger Ebert gave this movie 3 stars and stated “The movie has an innocence and charm that grow on you. It’s a reminder of the days before films got so cynical and unrelentingly violent.”

Emma

Release Date: 2020

Emma is a rom-com love story movie based on Jane Austen’s 1815 novel of the same name. Sure, the book is old, but the movie brings the story to life.

The movie follows Emma Woodhouse, a wealthy young woman living in 19th-century England who takes it upon herself to play matchmaker for her friends and family.

However, her well-intentioned efforts often backfire, leading to misunderstandings and leading her to find love for herself.

Starring in Jane Austen’s Emma is Anya Taylor-Joy as Emma; she’s best known for The Queen’s Gambit, The Witch, Morgan, The New Mutants, The Northman, Peaky Blinders, Last Night In Soho, and The Menu.

She’s joined by Johnny Flynn, Mia Goth, Callum Turner, Bill Nighy, and Josh O’Connor.

How To Lose A Guy In 10 Days

Release Date: 2003

Stepping away from the high school movies, How to Lose a Guy in 10 Days is about a woman named Andie (played by Kate Hudson) who works for a women’s magazine. She’s tasked with writing an article about how to lose a guy in 10 days.

Andie decides to put her theories to the test by purposely trying to drive away a man named Ben (played by Matthew McConaughey).

However, what Andie doesn’t know is Ben is also trying to win a bet with his friends by making a woman fall in love with him in 10 days.

As they both try to achieve their goals, they start developing feelings for each other, leaving both of them wondering what to do next.

As far as movies like 10 Things I Hate About You go, this is one of my favourites. It’s similar to the 90s teen drama as it involves a “bet” that goes wrong.

It’s a fun movie from the mid-2000s and will keep you entertained.

The Proposal

Release Date: 2009

The Proposal is a rom-com film about a high-strung and successful book editor, Margaret, who is facing deportation to Canada.

In order to avoid deportation, she “proposes” to her assistant, Andrew, and the two must pretend to be engaged for 90 days in order for her to get a green card.

But things become complicated when they discover that they might actually have feelings for each other.

The movie stars Sandra Bullock (Bird Box, The Lost City, The Blind Side) and Ryan Reynolds (Deadpool, Van Wilder, Free Guy, Just Friends, The Adam Project).

The Proposal is similar to 10 Things I Hate About You in that both films are romantic comedies that feature a fake relationship leading to genuine feelings.

Bring It On

Release Date: 2000

Bring It On is about a high school cheerleading squad and their journey to the national championships.

The squad is led by Torrance (Kirsten Dunst), who’s inherited the team from another cheerleader who got injured.

However, Torrance struggles to balance her responsibilities as captain with her personal life, relationship with her boyfriend, and the rival squad captain, Isis (Gabrielle Union).

To make matters worse, they discover that their previous captain had stolen all their cheer routines from another school in the inner city, leaving them without any routines they could perform.

As the movie is set in High School, it has the same cliques and friendship groups 10 Things I Hate About You has and has a similar comedy aspect.

We’re The Millers

Release Date: 2013

We’re the Millers is a comedy film about a small-time pot dealer, David, who loses his stash when he’s robbed.

In order to repay the main local drug lord, he’s forced to take his fake family on a drug run to Mexico.

Along the way, they encounter many challenges and hilarious situations. It’s one of the funniest movies out there; it surprised me.

The fake family includes Jennifer Aniston as a stripper, Emma Roberts as a runaway, and Will Poulter as a virgin. Sounds like a mixed bunch, doesn’t it, but it’s comedy gold.

The movie is similar to 10 Things I Hate About You in that both films revolve around a group of misfits, and both movies have a romantic subplot between the main characters. It also shares the “opposites attract” theme.

Palm Springs

Release Date: 2020

Palm Springs is a rom-com film about two people, Nyles and Sarah, who get stuck in a time loop while at a Palm Springs wedding. There could be worse time loops, I guess…

While the pair are stuck in the time loop, they begin to develop feelings for each other as they relive the day over and over and over again.

The movie is similar to 10 Things I Hate About You in that it features characters who initially resist falling in love but eventually succumb to their feelings.

The film stars Andy Samberg, known for Brooklyn Nine-Nine, Hot Rod, That’s My Boy, Storks, Cloudy With A Chance Of Meatballs, and Hotel Transylvania.

He’s joined by Cristin Milioti who’s starred in Made For Love, The Resort, How I Met Your Mother and Black Mirror.

Palm Springs is a fun and entertaining rom-com you’ll enjoy if you love movies like 10 Things I Hate About You.

A Cinderella Story

Release Date: 2004

A Cinderella Story is a rom-com movie about a high school girl named Sam who works as a waitress at her stepmother’s diner, all while trying to graduate.

She meets a popular and wealthy classmate named Austin online, yet the pair of them don’t know each other’s real identities. They agree to meet at the school ball, but when her stepmother and stepsisters discover who she’s been speaking to, they try to prevent her from going.

Luckily, Sam’s Fairy Godmother (played by Jennifer Coolidge) helps her get to the dance and transforms her into a beautiful princess, where she has the perfect date with Austin.

The movie is a mix between the classic Cinderella fairy tale and 10 Things I Hate About You.

The film stars Hilary Duff, Chad Michael Murray, Jennifer Coolidge (aka Stiffler’s Mum), and Dan Byrd.

Crazy, Stupid, Love

Release Date: 2011

Moving on from the high school scene, Crazy, Stupid, Love is a rom-com film about a middle-aged man named Cal whose wife asks for a divorce after 25 years of marriage.

Cal is heartbroken and struggles to move on. He turns to his younger best friend Jacob, who he meets in a bar, for guidance on how to be a “ladies’ man”.

Jacob overhauls Cal’s style, teaches him a few tricks to get the ladies, and turns him into a completely different guy.

Meanwhile, Cal’s teenage son tries to win the affection of his 17-year-old babysitter, who takes a liking to Cal.

The movie is funny, smart, and highly entertaining, much like 10 Things I Hate About You. The New York Times called the movie “remarkably sane and reasonably smart.”

The movie stars Steve Carell, Julianne Moore, Ryan Gosling, Emma Stone, and Kevin Bacon.

Ferris Bueller’s Day Off

Release Date: 1986

Ferris Bueller’s Day Off is a American teen comedy movie written, produced, and directed by John Hughes.

The film stars Matthew Broderick as Ferris Bueller, a high-school student who skips school for a day in Chicago, Illinois, with his girlfriend, Sloane Peterson and his best friend, Cameron Frye.

Along the way, they encounter numerous obstacles, including Ferris’s disapproving older sister Jeanie, principal Ed Rooney, and a suspicious police detective.

Ferris Bueller’s Day Off is a classic coming-of-age film that explores themes of rebellion, friendship, and the joys of youth.

It was a box office success upon its release and is a cult classic. The film is known for its memorable quotes, iconic characters, and a great soundtrack.

Plus it’s nice to see a high school movie move away from the whole “graduation party” setting, which is often done to death.

Deliver Us From Eva

Release Date: 2003

This rom-com film follows Gabrielle Union as Eva, a successful businesswoman who is constantly being set up on blind dates by her overbearing siblings… sounds like a hard life…

To get them off her back, Eva hires a young man named Ray (LL Cool J) to pretend to be her boyfriend. However, things get complicated when they start to develop real feelings for each other.

This movie is like 10 Things I Hate About You as it features a romantic storyline with plenty of comedic moments and has an emotional core.

Gabrielle Union is in both 10 Things I Hate About You and Deliver Us From Eva. She’s also been in Bad Boys II, Cheaper By The Dozen, and Bring It On.

She’s joined by LL Cool J; the American rapper come actor.

Save The Last Dance

Release Date: 2001

Another movie that moves away from the “graduation party” genre, Save the Last Dance is about a young white woman named Sara (played by Julia Stiles) who moves to a mostly black neighbourhood in Chicago after her mother’s death.

Sara enrols in a high school with very few white students, and she sticks out like a sore thumb. But, she meets a talented black dancer named Derek (played by Sean Patrick Thomas), who changes her perspective on life.

Despite their different backgrounds and different dance styles, the pair form a close bond and begin a romantic relationship.

Can this relationship work between the two? Or will their differences get in the way of their newfound romance?

This movie is similar to 10 Things I Hate About You as it’s an example of how opposites attract and addresses the everyday issues you experience during high school life. It also stars Julia Stiles, who was also in the 90s classic.

This love story shares a cast member from the 90s rom-com, Julia Stiles also stars in this movie. This actress has also been in The Prince And Me and Silver Linings Playbook.

Is there a movie you think I’ve missed? I would love to know so drop me a message in the comments section below.