30+ Movies That Bring Back Those High School Vibes Like Clueless

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As If! Stop stressing and check out these legendary teen films similar to ‘Clueless’ for your watchlist.

I vividly recall the year 1995 when my parents decided to hit the movies for their anniversary. To our astonishment, they picked Clueless, which had just debuted. My sister and I were stunned since it felt more geared towards us than them. But here’s the kicker: Clueless became a classic because it struck a chord with everyone. Sure, my parents were no longer teenagers, but they had once been. So, they found Clueless just as hilarious as we did. Themes of friendship, dating, and high school are nearly universal, which is why this cult favorite remains popular nearly three decades later, prompting us to seek out other unforgettable teen comedies.

While no film can fully replicate the ’90s charm of Cher Horowitz, it’s clear that movies like Clueless are hard to come by, especially since few comedies from the ’90s still resonate today. As Cher would say, they’re Monets: “From far away, it’s OK, but up close, it’s a big old mess.” Nonetheless, there are other films worth revisiting that will keep you and any teens at home entertained on movie night.

Movies Like Clueless to Add to Your Queue:

10 Things I Hate About You (1999)
Starring Julia Stiles and Heath Ledger, this film mirrors Clueless as it draws inspiration from classic literature. While Clueless is based on Jane Austen’s Emma, this one takes its cues from Shakespeare’s The Taming of the Shrew, all while delivering plenty of laughter.
Never Been Kissed (1999)
This charming comedy features a lovable protagonist and is set in high school, making it a great match for Clueless fans.
Emma (1996)
The original inspiration for Clueless, this film stars Gwyneth Paltrow and serves as a reminder of the classic tale’s charm. A modern adaptation was released in 2020 if you’d like to compare.
She’s All That (1999)
If you enjoy the makeover theme in Clueless, you’ll appreciate She’s All That. Rachael Leigh Cook’s character faces her fair share of criticism – “She used to be a farmer in those clothes,” anyone?
Easy A (2010)
Emma Stone shines in this film, which, like Clueless, is based on classic literature — in this case, Nathaniel Hawthorne’s The Scarlet Letter. It explores high school reputation and the rapid spread of rumors. Very relatable!
Fast Times At Ridgemont High (1982)
Jeff Spicoli’s laid-back attitude brings to mind Travis from Clueless, and since both films were directed by Amy Heckerling, the connection is evident. This film depicts a group of teens navigating love and part-time jobs.
Dazed and Confused (1993)
Featuring stoner characters like Slater, this film boasts a devoted following and pairs well with Clueless. To quote Wooderson, “It’d be a lot cooler if you did.”
Mean Girls (2004)
It’s impossible to discuss high school comedies without mentioning Mean Girls. Written by Tina Fey, this film remains a timeless classic, overflowing with quotable moments. If you have a teen who enjoyed Clueless, this is a must-see.
The Breakfast Club (1985)
While The Breakfast Club stands on its own, it deserves a spot on this list. The characters come from different cliques yet form a unique bond during detention, much like Tai and Travis finding love despite their social differences.
Can’t Hardly Wait (1998)
This underrated gem follows Preston Meyer’s (Ethan Embry) quest for love during a post-graduation party, reminiscent of what the Clueless crew might experience.
Romy and Michele’s High School Reunion (1997)
With a strong friendship at its core, this film echoes the bond between Cher and Dionne. Plus, the vibrant fashion at the end is just as delightful.
But I’m A Cheerleader (1999)
While it tackles themes of teen sexuality, this film humorously exaggerates stereotypes and features talents like Natasha Lyonne, Michelle Williams, and RuPaul.
Booksmart (2019)
Olivia Wilde’s directorial debut features two leading ladies, Kaitlyn Dever and Beanie Feldstein, who shine just like Alicia Silverstone and Stacey Dash did in Clueless.
Bring It On (2000)
Similar to Clueless, this film is packed with witty one-liners and memorable characters. “Spirit fingers” anyone?
Get Over It (2001)
An underrated film featuring a young Colin Hanks, this high school tale revolves around breakups, perfect for theater enthusiasts.
Heathers (1989)
A dark teen comedy, Heathers offers a chilling glimpse into high school cliques, where one girl takes extreme measures against her popular friends.

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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In summary, if you loved Clueless, there’s a treasure trove of films that capture the spirit of high school life, friendship, and self-discovery. From classic comedies to modern takes, these movies are sure to evoke nostalgia while entertaining a new generation.

Keyphrase: Movies like Clueless

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