30+ Movies Similar to Clueless That Will Bring You Back to High School

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Forget about it and queue up these legendary teen flicks just like Clueless!

By Jamie Worth
Updated: April 30, 2022
Originally Published: June 8, 2021

I’ll never forget it. The year was 1995, and my parents chose to celebrate their anniversary with a trip to the movies. When they picked Clueless, which had just been released, my sister and I were stunned. We thought the film was more aimed at our generation than theirs, making it a surprising choice. However, Clueless became a cultural phenomenon because it resonated across generations. Though my parents had long since left their teenage years behind, they could still appreciate the humor and themes of friendship, dating, and high school life. This universality is why Clueless remains beloved almost three decades later, and why we’re eager to find other classic teen comedies that capture that spirit.

Sure, nothing quite matches the ’90s charm of Cher Horowitz. Like, as if! It’s rare to find comedies from that era that still resonate today. As Cher famously quipped, they’re Monets: “From far away, it’s OK, but up close, it’s a big old mess.” Nevertheless, there are plenty of other films worth revisiting that will keep you and any teens in the house entertained during movie night.

Movies Similar to Clueless to Add to Your Queue

1. 10 Things I Hate About You (1999)
   Starring Julia Stiles and Heath Ledger, this film mirrors Clueless as it’s also inspired by classic literature. While Clueless draws from Jane Austen’s Emma, this movie adapts Shakespeare’s The Taming of the Shrew and is packed with humor.
2. Never Been Kissed (1999)
   This sweet comedy centers around a lovable lead character and is also set in high school, making it a fitting companion to Clueless.
3. Emma (1996)
   The original literary inspiration behind Clueless, this adaptation stars Gwyneth Paltrow. A newer version was also released in 2020, perfect for comparison.
4. She’s All That (1999)
   If you enjoyed the makeover aspect of Clueless, you’ll find a similar theme in She’s All That, featuring Rachael Leigh Cook as Laney Boggs who faces her own set of challenges.
5. Easy A (2010)
   Emma Stone shines in this film that takes a modern twist on Nathaniel Hawthorne’s The Scarlet Letter, exploring high school reputation and the rumors that can quickly spiral out of control.
6. Fast Times At Ridgemont High (1982)
   Another classic from director Amy Heckerling, this film follows a group of high schoolers navigating love and life. Jeff Spicoli’s laid-back personality is reminiscent of Travis in Clueless.
7. Dazed and Confused (1993)
   Featuring its own collection of memorable characters, this cult classic is perfect for fans of Clueless. Plus, it shares a similar vibe with its portrayal of high school life.
8. Mean Girls (2004)
   No teen comedy list would be complete without Mean Girls. Written by Tina Fey, it’s a cultural touchstone that remains quotable even years later, making it a must-watch for fans of Clueless.
9. The Breakfast Club (1985)
   This iconic film dives into the lives of five high school students from different social backgrounds who bond during detention. It resonates with the themes of acceptance found in Clueless.
10. Can’t Hardly Wait (1998)
    An underrated gem, this film captures the excitement and angst of high school romance, similar to the dynamics seen in Clueless.
11. Romy and Michele’s High School Reunion (1997)
    Focusing on a strong friendship, Romy and Michele mirror the bond of Cher and Dionne while showcasing vibrant fashion.
12. But I’m A Cheerleader (1999)
    This film takes a satirical look at teen sexuality and stereotypes, featuring stars like Natasha Lyonne and Michelle Williams.
13. Booksmart (2019)
    Olivia Wilde’s directorial debut features two strong female leads that echo the dynamic seen in Clueless.
14. Bring It On (2000)
    With its sharp dialogue and memorable one-liners, this cheerleading comedy has the same infectious energy as Clueless.
15. Get Over It (2001)
    An often-overlooked film featuring Colin Hanks, this high school comedy is perfect for theater enthusiasts.
16. Heathers (1989)
    This dark comedy offers a twisted take on high school cliques and the perils of popularity.

More Movies Like Clueless to Watch:

• Orange County (2002)
• Legally Blonde (2001)
• Wild Child (2008)
• The DUFF (2015)
• Sixteen Candles (1984)
• Drive Me Crazy (1999)
• Better Off Dead (1985)
• Can’t Buy Me Love (1987)
• Ferris Bueller’s Day Off (1986)
• Some Kind of Wonderful (1987)
• Empire Records (1995)
• Pretty in Pink (1986)
• Valley Girl (1983, 2020)
• Loser (2000)
• The Kissing Booth (2018)
• A Cinderella Story (2004)
• Varsity Blues (1999)
• How to Deal (2003)
• Girls Just Want to Have Fun (1985)
• Mean Girls 2 (2011)

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Summary

This collection of films, from 10 Things I Hate About You to Mean Girls, captures the spirit of Clueless while offering a variety of themes related to friendship, love, and the complexities of high school life. Whether you’re revisiting classics or discovering new favorites, these movies promise plenty of laughs and nostalgia.

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