20+ Teen Movies Like Clueless To Relive The High School Nostalgia

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Sarthak Koul
Sarthak brings a technical perspective to the everyday aspects of life through his blogs. Breaking down the storyline of movies and shows is something he enjoys thoroughly. He firmly believes in contributing to this flawed and beautiful world in his own way. His mantra is to take things one day at a time.

If you enjoyed watching the Amy-Heckerling-directed teen comedy flick, Clueless, you’ll love what we’ve in store for you ahead. Counted as a classic coming-of-age flick from the 90s and one of the best teen films of all time, here in this article, we’ll provide you with a list of similar movies like Clueless. 

As a cause-and-effect dynamic of amassing a cult following, the movie continued its legacy with a series of books and even a spin-off television sitcom sharing the same title. Produced by the duo of Scott Rudin and Robert Lawrence, the 1995-released teen flick is a loose adaptation of Jane Austen’s novel titled Emma.

With an iconic cast of Alicia Silverstone, Stacey Dash, Brittany Murphy, and Paul Rudd, the storyline takes on the modern-day setting of Beverly Hills. To recap, the plot of Clueless revolves around a popular high school teenager who despite her wit and intelligence in relationships finds herself clueless in matters of her own heart.

If you had fun through the screenplay of the soft satire of teen films that is Clueless, read on along as we are about to share over a dozen other movies that capture the essence of the magic of Cher Horowitz in our edition of teen movies like Clueless.

Top 7 Movies Like Clueless

Movies Like Clueless
Source: Screen Rant

#1 Mean Girls (2004)

Kicking off the list with the female-frontend humor flick of the early 2000s – Mean Girls. Starring the exceptional cast of Lindsay Lohan and Rachel McAdams among others, the Mark-Waters-directed film ranks among the greatest teen comedies of all time.

Based on Rosalind Wiseman’s self-help book, Queen Bees and Wannabes, the plot of Mean Girls follows the story of a teenage girl, Cady Heron finding her way in the modern American high school. However, things take a surprising twist when she falls for the ex-boyfriend of the queen bee, Regina George.

Runtime: 1h 37min 

IMDB: 7.0/10

Director: Mark Waters

Cast: Lindsay Lohan, Rachel McAdams, Tim Meadows, Ana Gasteyer, Amy Poehler, Tina Fey

#2 10 Things I Hate About You (1999)

If you’ve yet to see 10 Things I Hate About You, you’re missing out on one of the most iconic romantic comedy flicks of the ’90s. The Gil-Junger-directed movie finds its similarity to Clueless as both are based on prior fictional works with the former being a loose adaptation of William Shakespeare’s The Taming of the Shrew

Starring Julia Stiles, Joseph Gordon-Levitt, and the exceptional Heath Ledger in the star cast, the movie follows the American high school setting. The plot of the rom-com drama takes on the story of a popular and beautiful Bianca Stratford who can’t go out on a date until and unless her shrewd older sister does.

Runtime: 1h 37min 

IMDB: 7.3/10

Director: Gil Junger

Cast: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, Larisa Oleynik, Larry Miller, David Krumholtz, Andrew Keegan, Susan May Pratt

#3 Emma (1996)

Up next, we have the movie adaptation of the book by Jane Austen that served as the creative basis for  Amy Heckerling’s Clueless. Apart from Gwyneth-Paltrow-starrer Emma, there’s also a 2020 version of the period comedy film.

Released at the 1996 Seattle International Film Festival, Emma’s plot takes on the story of a naïve young 19th century Englishwoman. While considering herself as a matchmaker within her community of friends and neighbors, Emma nearly misses out on her own chance of finding true love.

Runtime: 2h 

IMDB: 6.7/10

Director: Douglas McGrath

Cast: Gwyneth Paltrow, Toni Collette, Alan Cumming, Ewan McGregor, Jeremy Northam, Greta Scacchi, Juliet Stevenson, Polly Walker

#4 She’s All That (1999)

Talking about high school movies like Clueless, we can’t just forget to mention one of the most popular teen flicks of the late 1990s, She’s All That. Directed by Robert Iscove, the romantic comedy features the likes of Rachael Leigh Cook, Freddie Prinze Jr., and Paul Walker.

The storyline follows a high school jock Zack Siler who after being publicly dumped by his prom-queen girlfriend ends up making a bet to transform a geeky, unattractive girl into the school’s new prom queen. What follows is a series of not-so-typical fairy tale events filled with outstanding performances of the lead actors. 

Runtime: 1h 35min 

IMDB: 5.9/10

Director: Robert Iscove

Cast: Rachael Leigh Cook, Freddie Prinze Jr., Matthew Lillard, Paul Walker, Kevin Pollak, Jodi Lyn O’Keefe, Kieran Culkin, Elden Henson, Kimberly Jones, Usher Raymond, Anna Paquin

#5 Legally Blonde (2001)

Coming up next, we’ve got Reese Witherspoon in Robert Luketic’s feature-length directorial debut with the 2001 comedy film, Legally Blonde. Alongside Witherspoon, the star cast features the likes of Luke Wilson, Selma Blair, and Matthew Davis.

Based on Amanda Brown’s comedy novel of the same name, the plot of Legally Blonde follows a sorority girl, Elle Woods, who in a series of interesting twists attempts to win back her ex-boyfriend. Join Elle on her journey as she overcomes stereotypes against blondes while aiming for a Juris Doctor degree at Harvard Law School.

Runtime: 1h 36min 

IMDB: 6.4/10

Director: Robert Luketic

Cast: Reese Witherspoon, Luke Wilson, Selma Blair, Matthew Davis, Victor Garber, Jennifer Coolidge

#6 Never Been Kissed (1999)

Based on the similar high school premise as Clueless, the Raja-Gosnell-directed rom-com flick features an all-star cast of Drew Barrymore, Jessica Alba, David Arquette, along with many others including even James Franco in his film debut. 

The plot of Never Been Kissed takes on the story of Josie Gellar, a copy editor at the Chicago Sun-Times. As a part of an undercover research assignment, Josie enrolls at a high school giving her the chance to recreate her experience.

Runtime: 1h 47min 

IMDB: 6.1/10

Director: Raja Gosnell

Cast: Drew Barrymore, Jeremy Jordan, David Arquette, Leelee Sobieski, Michael Vartan, Molly Shannon, John C. Reilly, Garry Marshall

#7 Easy A (2010)

Up next, we’ve got the 2010 teen romantic comedy flick written by Bert V. Royal. Drawing some inspiration from Nathaniel Hawthorne’s novel The Scarlet Letter, the high school teen movie directed by Will Gluck features Emma Stone in the lead role.

Having first premiered at the Toronto International Film Festival, Easy A went on to make nearly 10x its initial production budget of $8 million at the box office. The plot of the movie follows the story of a 17-year-old high school girl Olive who uses a rumored lie about herself for her own benefit.

Runtime: 1h 32min 

IMDB: 7.0/10

Director: Will Gluck

Cast: Emma Stone, Amanda Bynes, Thomas Haden Church, Penn Badgley, Patricia Clarkson, Lisa Kudrow, Cam Gigandet, Malcolm McDowell, Aly Michalka, Stanley Tucci

Other Movies Like Clueless That Are Worth Watching

  • Dazed and Confused (1993)
  • Fast Times At Ridgemont High (1982)
  • Can’t Hardly Wait (1998)
  • Bring It On (2000)
  • The Crush (1993)
  • Heathers (1989)
  • Booksmart (2019)
  • The Breakfast Club (1985)
  • Uptown Girls (2003)
  • Pretty in Pink (1986)
  • Love, Simon (2018)
  • Romy and Michele’s High School Reunion (1997)
  • But I’m A Cheerleader (1999)
  • Get Over It (2001)

Wrapping Up

This brings us to the conclusion of our article on similar movies like Clueless. From some of the best ‘90s teen flicks to the more modern take on high school rom-com, we’ve covered about twenty-something movies like Clueless that ooze a similar high school storyline.

Make sure to share the article with your friends if you liked the content. We’d love to hear from you! So, comment down below with your favorite teen flicks from the list. And for more such interesting lists and content related to the Entertainment, keep visiting Path of EX. 

Feature Image Credit: The Cinemaholic

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