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As If! Ditch the drama and add these iconic teen films reminiscent of ‘Clueless’ to your watchlist!
By Jamie Carter
Updated: April 30, 2022
Originally Published: June 8, 2021
I can vividly recall the year 1995 when my parents surprised my sister and me by choosing to see Clueless for their anniversary. We thought it was an odd pick, considering it felt more tailored to us than to them! Yet, Clueless proved to be a timeless favorite for audiences of all ages. Even though my parents were long past their teen years, they still found humor in the film, just as we did. The themes of friendship, romance, and high school experiences are universal, which is why this classic remains beloved nearly three decades later. So, if you’re looking for other unforgettable teen comedies akin to Clueless, look no further!
While nothing quite captures the ’90s charm of Cher Horowitz, there are still plenty of gems worth revisiting. Here’s a collection of movies that will ensure your next movie night is anything but boring!
Movies Like Clueless to Add to Your Queue
- 10 Things I Hate About You (1999)
With Julia Stiles and Heath Ledger in leading roles, this film echoes Clueless’s charm as it is also inspired by classic literature—Shakespeare’s The Taming of the Shrew. - Never Been Kissed (1999)
This delightful comedy features a relatable main character navigating high school life, making it a perfect pairing with Clueless. - Emma (1996)
The original inspiration for Clueless, this adaptation starring Gwyneth Paltrow showcases the timeless story of romance and misunderstanding. A new adaptation was released in 2020 if you’re curious for a modern take. - She’s All That (1999)
If you enjoyed the makeover moments in Clueless, you’ll appreciate the transformation of Laney Boggs in this popular film. - Easy A (2010)
Emma Stone shines in this witty film, which is inspired by Nathaniel Hawthorne’s The Scarlet Letter and delves into high school reputation and gossip. - Fast Times at Ridgemont High (1982)
Directed by Amy Heckerling, who also helmed Clueless, this classic follows a group of teens navigating love and life in high school. - Dazed and Confused (1993)
Another cult favorite, this film features stoner characters similar to those in Clueless and captures the essence of high school friendships. - Mean Girls (2004)
A must-watch in the realm of teen comedies, Tina Fey’s script ensures this film remains quotable and relatable for years to come. - The Breakfast Club (1985)
Focusing on the unique connections formed between different social groups, this film mirrors themes of acceptance found in Clueless. - Can’t Hardly Wait (1998)
An underrated classic, this film features a high school party that could easily rival the epic gatherings seen in Clueless. - Romy and Michele’s High School Reunion (1997)
With a strong friendship at its core, this film’s fashion and humor parallel that of Cher and Dionne. - But I’m A Cheerleader (1999)
This satire addresses teen sexuality and stereotypes, featuring standout performances from Natasha Lyonne and RuPaul. - Booksmart (2019)
Olivia Wilde’s directorial debut showcases two high-achieving friends on the verge of graduation, reminiscent of the strong bond shared by Cher and Dionne. - Bring It On (2000)
Packed with memorable quotes and sharp writing, this cheerleading film has a similar comedic flair to Clueless. - Get Over It (2001)
Featuring a young Colin Hanks, this high school comedy is about heartbreak and perfect for theater enthusiasts. - Heathers (1989)
A darkly humorous take on high school cliques, this film explores the extreme lengths one girl goes to in order to break free from the toxic environment.
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:
If you loved Clueless, you’ll enjoy these 30+ movies that capture the spirit of high school life, friendship, and romance. From classic comedies like 10 Things I Hate About You to modern hits like Booksmart, there’s no shortage of films to keep you entertained and nostalgic.