10 Things I Hate About You, the 1999 teen romantic comedy, is a bonafide classic. People love watching Heath Ledger and Julia Stiles go from being enemies to lovers. If you love this movie, you should check out the 12 best movies like 10 Things I Hate About You.
1. Get Over It (2011)
English 1h 27m IMDb
Director: Tommy O’Haver
Stars: Kirsten Dunst, Ben Foster, Melissa Sagemiller
10 Things I Hate About You and Get Over It are both Shakespeare adaptations starring 2000s teens. But while 10 Things is based on Taming of the Shrew, Get Over It takes its inspiration from A Midsummer Night’s Dream. Although the movies have a lot in common, Get Over It is definitely the zanier of the two.
The movie follows Berke, a popular basketball player who recently got dumped. He turns to Kelly, his best friend’s little sister, to help him win his ex back. After joining his ex in the school’s spring musical, he realizes that Kelly might actually be the one he wants.
Get Over It isn’t quite as charming as 10 Things, but it’s a fun teen rom-com with lots of great Y2K fashion. In fact, the movie feels like a time capsule. It even features pop stars from the time, like Vitamin C, Sisqo, and Shane West.
2. The Prince and Me (2004)
English 1h 27m IMDb
Director: Tommy O’Haver
Stars: Kirsten Dunst, Ben Foster, Melissa Sagemiller
In The Prince & Me, Julia Stiles is relentlessly pursued by a foreign boy who’s hiding a secret. While that might sound exactly like the plot of 10 Things, we promise that these two movies aren’t telling the exact same story.
Instead, the movie follows Eddie, a rebellious prince who wants to live a normal life. He travels to an American college where he meets Paige, a hard-working pre-med student. Eddie falls hard for Paige right away, but she’s worried that a relationship could get in the way of her studies, especially when she discovers who Eddie really is.
This movie is more of a romance than a comedy, but it still has some very funny moments. If you fall in love with Paige and Eddie, there are even three sequels for you to enjoy, though they unfortunately don’t feature Julia Stiles.
3. She’s All That (1999)
English 1h 35m IMDb
Director: Robert Iscove
Stars: Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard
She’s All That might be the most iconic teen romantic comedy of all time. Loosely based on Pygmalion, it follows Zach, a popular guy who makes a big bet after a breakup. He claims that he can make any girl at school the next prom queen, even the unpopular Laney Boggs.
While the plot of the movie is fun, the real thing that makes She’s All That shine is its lead. Rachael Leigh Cook and Freddie Prinze Jr. both give fantastic performances here, and the two have fantastic chemistry. The rest of the cast, which includes Paul Walker, Kieran Culkin, and Matthew Lillard, is also terrific.
If you love movies that prove that opposites attract, you’ll fall hard for She’s All That. Not only is this a wonderful movie, but it also has a catchy soundtrack and amazing outfits, like the red dress Laney wears on her date.
4. She’s the Man (2006)
English 1h 45m IMDb
Director: Andy Fickman
Stars: Amanda BynesLaura RamseyChanning Tatum
She’s the Man is an updated version of yet another Shakespeare play, Twelfth Night. It stars Amanda Bynes as Viola, a talented soccer player who masquerades as her brother, Sebastian, to play on an all-boys team. Things get complicated when she falls for Duke, another player on the team.
Channing Tatum wasn’t the first choice for the role of Duke, but Amanda Bynes fought hard to make sure he was cast. It’s clear that she knew what she was doing. The chemistry between the two actors is one of the best parts of the film.
The romance at the center of the movie will make you swoon, and you’ll love the comedy here too. Amanda Bynes rose to fame on the sketch comedy show All That, and she puts her comedy skills to good use here. The movie features other comedy superstars as well, like David Cross.
5. A Knight’s Tale (2001)
English French Latin 2h 12m IMDb
Director: Brian Helgeland
Stars: Heath Ledger, Mark Addy, Rufus Sewell
If you love Heath Ledger’s lovable performance in 10 Things, you’ll want to check him out in A Knight’s Tale. This romantic comedy film follows William, a peasant squire who poses as a noble to enter jousting tournaments. William falls for a noblewoman named Jocelyn, but will she still love him when she finds out who he really is?
A Knight’s Tale takes its name from the Chaucer story of the same name. However, this movie isn’t a modern-day adaptation of the story. Although the film features modern music, the story is set in medieval times.
Even though this movie has a lot of romance and comedy, it’s also a great adventure story. People who don’t normally like romantic comedies might find themselves invested in this film. It’s another example of how great Heath Ledger was as a romantic lead.
6. Never Been Kissed
English 1h 47m IMDb
Director: Raja Gosnell
Stars: Drew Barrymore, David Arquette, Michael Vartan
Josie was a complete outcast in high school. When she’s asked to pose as a high school student to get an undercover story, she welcomes the opportunity to get a second chance at high school life. However, she doesn’t expect to fall hard for her handsome high school teacher.
If you love romantic comedies about high school and secrets, you’ll immediately get sucked into the story of Never Been Kissed. Drew Barrymore is fantastic in the role of Josie, and she has amazing chemistry with her love interest, who’s played by Michael Vartan.
You’ll swoon over all the romantic scenes, and you’ll also love the outfits. The movie is known for its amazing fashion moments, and it even kicked off some fashion trends when it was released in 1999. It’s an amazing movie to watch if you’re looking for some fashion inspiration.
7. Clueless (1995)
English Spanish 1h 39m IMDb
Director: Amy Heckerling
Stars: Alicia Silverstone, Stacey Dash, Brittany Murphy
Inspired by Jane Austen’s Emma, Clueless is a true classic. It stars Alicia Silverstone as Cher, a popular girl who decides she wants to become a romantic matchmaker. However, after an attempt at matchmaking goes wrong, she starts to think she might be totally clueless when it comes to love.
If you love watching enemies realize that they’re head-over-heels for each other, you’ll love the romantic relationship at the center of Clueless. Alicia Silverstone and Paul Rudd have a ton of chemistry, and you’ll realize that they’re in love with each other long before the characters do.
The movie also has an iconic performance from the late Brittany Murphy. Even though this was her first speaking role in a feature film, she’s a natural in front of the camera. From “as if” to “whatever,” this is a movie you’ll find yourself quoting all the time.
8. Easy A (2011)
English 1h 32m IMDb
Director: Will Gluck
Stars: Emma Stone, Amanda Bynes, Penn Badgley
When Olive lies to her best friend about losing her virginity, she doesn’t think it will be a big deal. Before long, however, her little lie spirals out of control. Inspired by The Scarlet Letter, Olive decides to embrace her bad reputation and starts wearing a bright red “A.”
This was Emma Stone’s breakout role, and it’s easy to see why the movie made her a star. She’s a natural comedian with a strong screen presence. It’s impossible not to root for her throughout the movie, especially when she starts to get closer to her crush Todd.
Some of the best teen comedies of all time are based on classic works of literature, and Easy A is no exception. It’s a blast to watch a good girl pretend to be bad, and it’s even more fun to watch her figure out how to get her good reputation back.
9. Can’t Hardly Wait (1998)
English 1h 40m IMDb
Directors: Harry Elfont, Deborah Kaplan
Stars: Jennifer Love Hewitt, Ethan Embry, Charlie Korsmo
If you love the party scenes in 10 Things, then you’ll adore Can’t Hardly Wait, a teen hangout movie about a blowout party on the last day of high school. Preston knows that the party is his last chance to tell his crush, Amanda, how he really feels. The movie also follows several of Preston’s classmates as they try to end their high school career with a bang.
While this is a Y2K-era teen rom-com, it also feels inspired by teen movies of the 80s! During the credits, you’ll see character epilogues that feel just like the ones in Fast Time at Ridgemont High!
If you watch a lot of teen comedies, you’ll see familiar faces throughout the film. Ethan Embry and Jennifer Love Hewitt appear in the lead roles, but the movie also features actors like Seth Green, Selma Blair, Jaime Pressley, Melissa Joan Hart, and Jerry O’Connell.
10. Whatever It Takes (2000)
English 1h 34m IMDb
Director: David Raynr
Stars: Shane West, Marla Sokoloff, Jodi Lyn O’Keefe
In Whatever It Takes, two teenage boys join forces to help each other win the girls of their dreams. Nerdy Ryan has a huge crush on popular girl Ashley, while jock Chris is crazy about the brainy Maggie. As the boys get closer to winning over their crushes, they start to think they might be going for the wrong girls.
This is a fun romantic comedy that has quite a few similarities to 10 Things. The relationship between Ryan and Chris feels a lot like the relationship between Cameron and Patrick. There are also some fun musical scenes!
Like many teen comedies, everything builds up to prom. The prom scene in this movie doesn’t disappoint, especially when you see James Franco in his formal wear. If you love teen rom-com from this era, this is a fun movie that’s worth a watch!
11. Bring It On (2000)
English 1h 38m IMDb
Director: Peyton Reed
Stars: Kirsten Dunst, Eliza Dushku, Jesse Bradford
While Bring It On is all about cheerleading, it’s a movie that any fan of teen films will love! It follows newly-crowned cheerleading captain Torrence, who discovers that her high school’s championship cheerleading team has been stealing its routines. As she tries to help the team recover, she meets Misty, a talented gymnast, and her punk rock brother, Cliff.
There’s a lot to love about the relationship between Torrence and Cliff, but at its heart, this movie is all about its leading ladies. It features amazing performances from Kirsten Dunst, Eliza Dushku, and Gabriel Union. The story is involving, even if you don’t care about cheerleading, and there are plenty of hilarious scenes.
Bring It On also spawned several sequels, though none of them were as popular as the original film. If you watch this movie, make sure you check out the end credits, which feature the 80s hit “Mickey.”
12. Drive Me Crazy (1999)
English 1h 31m IMDb
Director: John Schultz
Stars: Melissa Joan Hart, Adrian Grenier, Stephen Collins
When Nicole’s crush Brad asks out another girl, Dulcie, she decides to make him jealous. She enlists Chase, her childhood friend and Dulcie’s ex, to pretend to be her boyfriend. While the two don’t get along at first, they soon find themselves falling for each other.
The movie takes its name from the hit Britney Spears song “Drive Me Crazy,” which also appears on the movie’s soundtrack. Spears featured the stars of the movie, Melissa Joan Hart and Adrian Grenier, in the music video for the song. The soundtrack also includes artists like The Backstreet Boys and Barenaked Ladies.
While the ending of the movie might be a bit predictable, it’s still fun to watch the lead characters fall in love, especially when they’re bickering with each other. If you’ve already watched the most popular teen comedies, you should set aside some time to watch this frequently overlooked film.
Instead of watching 10 Things over and over again, why not try something new? The 12 best movies like 10 Things I Hate About You are all fun movies that are worth a watch or two. You might even wind up discovering your new favorite film!