I remember it well. The year was 1995, and my parents decided to go to the movies to celebrate their anniversary. When they chose Clueless, which had just premiered days before, my sister and I were in disbelief. It seemed like the film was targeted more for us than them, so it was a shocking choice. But here’s the thing: Clueless became so iconic because it resonated with everyone. Sure, my parents weren’t teenagers anymore, but they had been at one point in their lives. So, they still found Clueless to be just as funny as we did. Growing up, friendship, dating, high school — these are nearly universal touchstones. It’s the reason the cult classic’s popularity endures roughly three decades later and the reason we’re all on the hunt for other timeless teen comedy movies like Clueless.
Don’t get me wrong; there aren’t any movies that fully capture the ’90s YA magic of Cher Horowitz. Like, as if, right? Movies like Clueless seem like a bit of a rarity, especially since not many comedies from the ’90s still hold up so beautifully today. In the immortal words of Cher herself, they’re Monets: “From far away, it’s OK, but up close, it’s a big old mess.”
That said, it’s not the only movie worth revisiting. Here are some other great titles that’ll keep you (and any teens in the household) from buggin’ next movie night.
Movies Like Clueless to Add to Your Queue
1. 10 Things I Hate About You (1999)
With Julia Stiles and Heath Ledger in the lead, this one’s a movie like Clueless since it’s also loosely based on a prior work of fiction. Clueless was meant to take the form of Emma by Jane Austen. 10 Things I Hate About You is much like The Taming of the Shrew by William Shakespeare, but with plenty of laughs.
2. Never Been Kissed (1999)
Never Been Kissed is another comedy with a sweet lead character you want to root for. Plus, it’s based around high school, making it even more similar.
3. Emma (1996)
As mentioned, this was the book that served as the creative basis for Clueless. However, Emma was also a movie in 1996 starring Gwyneth Paltrow (so, probably a good call by Clueless‘s filmmakers not to lean wholly into the inspo and have to compete with Gwynnie!). A new version of Emma debuted in 2020, in case you want to watch that for comparison too.
4. She’s All That (1999)
Like the “makeover” element in Clueless? Tai used to “be a farmer in those clothes. Laney Boggs, played by Rachael Leigh Cook, also happened to hear such petty insults in the film She’s All That. This one airs on television a bunch, so it’s easy to catch.
5. Easy A (2010)
Emma Stone knocked it out of the park in this movie! And like Clueless and others on this list, it’s based on a book — The Scarlet Letter by Nathaniel Hawthorne. But, it’s also about reputation in high school and how quickly rumors can pass. Can you say relatable?
6. Fast Times At Ridgemont High (1982)
It’s hard to look at Jeff Spicoli and not think that he may have slightly influenced Travis from Clueless, played by Breckin Meyer. Amy Heckerling actually directed both movies, so it’s not far off to see the connection. Fast Times At Ridgemont High is also about a high school and a group navigating through love and part-time jobs.
7. Dazed and Confused (1993)
Speaking of stoner characters, Slater from Dazed and Confused is yet another that’d likely be friends with Travis from Clueless. This movie has a similar cult following and would be a fun watch. Or, to quote Dazed and Confused‘s Wooderson (aka Matthew McConaughey), “It’d be a lot cooler if you did.”
8. Mean Girls (2004)
It’s impossible to talk about high school comedies and not mention Mean Girls. The film, written by Tina Fey, is one of Lindsay Lohan’s best. It remains funny years after its release, and we’ll never stop busting out Mean Girls quotes in casual conversation. So if you live in a house with a teen who liked Clueless, this one is a solid bet for movie night.
9. The Breakfast Club (1985)
While The Breakfast Club is in a category all its own, it’s hard not to include it on a list of movies like Clueless. Also focused around a high school, the characters all come from different social groups yet manage to create a special relationship, all thanks to detention. Much like Tai and Travis finding love in the end despite being in different popularity circles, The Breakfast Club shows we should all embrace what makes us different.
10. Can’t Hardly Wait (1998)
Can’t Hardly Wait is an underrated comedy that still gets a lot of laughs. It’s hard not to root for Preston Meyer (played by Ethan Embry), who’s hopelessly in love with Amanda Beckett (played by Jennifer Love Hewitt). If we ever got to see the big post-graduation party thrown by the teens from Clueless, it might look a little bit like the epic party thrown in Can’t Hardly Wait.
11. Romy and Michele’s High School Reunion (1997)
Why is this film like Clueless? Well, it makes the list for a few reasons. One, Romy and Michelle have a strong relationship, much like Cher and Dionne. And the fashion — especially at the very end — is equally as bright and fun.
12. But I’m A Cheerleader (1999)
This film, starring Natasha Lyonne, is more about teen sexuality than Clueless. However, it also plays on stereotypes in a pretty exaggerated way. Bonus: It stars Michelle Williams and RuPaul.
13. Booksmart (2019)
You might have heard a lot about this film. For one, it was the directorial debut for Olivia Wilde, who’s still pursuing directing over acting. Secondly, the two leads — much like Alicia Silverstone and Stacey Dash — steal the show. Kaitlyn Dever and Beanie Feldstein play Amy and Molly, and they’re ones to watch in the future.
14. Bring It On (2000)
Much like Clueless, Bring It On has several excellent one-liners that still make their way into conversations today. If you ever hear someone talk about “spirit fingers,” surely that’s a Bring It On reference. The writing is equally sharp, and the characters are equally lovable.
15. Get Over It (2001)
This is yet another underrated title featuring a young Colin Hanks — who, shockingly, has a supporting role. The high school-based film is all about breaking up and perfect for theater kids.
More Movies Like Clueless to Watch
16. Orange County (2002)
17. Heathers (1989)
18. Legally Blonde (2001)
19. Wild Child (2008)
20. The DUFF (2015)
21. Sixteen Candles (1984)
22. Drive Me Crazy (1999)
23. Better Off Dead (
24. Can’t Buy Me Love (1987)
25. Ferris Bueller’s Day Off (
26. Some Kind of Wonderful (1987)
27. Empire Records (1995)
28. Pretty in Pink (1986)
29. Valley Girl (1983, 2020)
30. Loser (2000)
31. The Kissing Booth (2018)
32. A Cinderella Story (2004)
33. Varsity Blues (1999)
34. How to Deal (2003)
35. Girls Just Want to Have Fun (1985)