1995's Clueless, starring teen idol Alicia Silverstone and a young Paul Rudd, is one of the most iconic movies the 90s produced. To this very day, this cinematic masterpiece in its own right still enchants audiences. The cult following it continues to produce decades after its release date is a testament to its qualities and themes that resonated with the public.
Very loosely based on British author Jane Austen's 19th-century novel "Emma", the movie had its own kind of flavor that many studios struggle to replicate today. If you've watched Clueless more times than you can count and are in dire need of something new, we have 10 movies you'll definitely want to check out.
10 Mean Girls (2004)
Mean Girls is one of those pop culture phenomenons that come by once in a generation. In many ways, this high-school comedy was the Clueless of the 2000s and introduced a series of actors that went on to do amazing things.
Following the ins and outs of the high-school world with witty humor, an outsider perspective, and too many iconic lines to keep track of, fans of Clueless will find Tina Fey's passion project a delight - and it might even hit a little too close to home for some!
9 10 Things I Hate About You (1999)
The 90s truly were the Golde Age of teen movies and coming of age films. The same decade that produced Clueless also produced 10 Things I Hate About You, a comedy slash drama slash romance loosely inspired by one of William Shakespeare's most infamous plays.
Starring Julia Stiles and Heath Ledger, the movie is a heartfelt and hilarious tale of young love, sibling rivalry, and teenagers just trying to find their own identities in a world that constantly pushes them to be someone else.
8 Sixteen Candles (1984)
Although the 90s was the decade that absolutely solidified the popularity of the teen movie genre, the 80s weren't very far behind. And it was movies like Sixteen Candles that served as the predecessors for projects like Mean Girls and Clueless.
There's nothing extremely original about this particular film, but at the time, it was one of the first of its kind. Following the 16th birthday of the main character, as she navigates the complexities and embarrassments of high-school life, any fan of Clueless will find common ground to love in Sixteen Candles.
7 The Breakfast Club (1985)
Sixteen Candles might have helped Molly Ringwald with her climb to fame, but it was 1985's The Breakfast Club that cemented her status as a teen idol at the time. Now known as one of the most iconic movies of the genre ever made, The Breakfast Club is a must-watch for those looking for a more raw portrayal of teenagehood.
The concept of bringing five completely different individuals together as they go through one of the hardest and most confusing phases of life was first seen here, and although it's not as charming as Clueless, it's just as compelling.
6 To All The Boys I've Loved Before (2018)
While something was lost throughout the late 2000s and early 2010s in the realm of teen movies, the late 2010s brought it back and revamped the genre into something more genuine, ditching the notions of perfection in favor of a more realistic depiction of characters.
Netflix's To All The Boys I've Loved Before is a great example of this new age teen movie. The sappy love story is still there, but the elements that surround the narrative are more relatable and charming in their own way.
5 The DUFF (2015)
For those who prefer the escapist aspect of movies as opposed to realistic portrayals of characters and narratives, 2015's The DUFF is the perfect treat. The setting and overall feel of the movie will definitely resonate with hardcore fans of Clueless.
The DUFF is a hilarious tale of a high-school girl who's on a quest to find her own identity away from her friends after finding out the cruel way the world perceives her. Plenty of will-they-won't-they on the romance front as well!
4 She's All That (1999)
The "high-school jock falls for the nerdy girl who was actually beautiful all along behind those glasses" trope has been beaten to a pulp. But when She's All That premiered in 1999, it was the first time in many years that audiences saw it play out on screen.
The premise itself might no longer be original and can be somewhat problematic, but the dimension given to the characters (as much as one can expect from a 90s teen movie) makes it worth a watch, especially for fans of Clueless and its charm.
3 Cruel Intentions (1999)
Cruel Intentions doesn't get as much credit as it deserves. This 1999 movie starring Sarah Michelle Gellar, Ryan Philippe, and Reese Witherspoon is a wonderful take on the machiavellian and cruel aspects of high-school culture.
Sure, it's exaggerated to the highest possible degree, but what good teen movie isn't? Cruel Intentions might not be as fun-loving as Clueless, but it's equally as captivating.
2 Legally Blonde (2001)
On the topic of Reese Witherspoon, let's talk about Legally Blonde. It would be almost immoral to compile a list like this and ignore the 2001 masterpiece that was this movie, which single-handedly served a feminine, loving, blonde woman who was also smart and independent to an audience that revelled in putting down such a notion.
It's almost like Elle could be a grown-up version of Cher, with the outfits, the hair, the life philosophy, and the never-ending wit and knack for putting others in their place with kindness and assertiveness.
1 Emma (2020)
Clueless was, after all, based on the novel by Jane Austen the public knows as "Emma". What a better way to relive Cher's personality and hilarious conundrums other than to go straight to the source?
Many adaptations of the book have been done, in many shapes and sizes. However, the most recent one, Emma, is the one who will most likely resonate with the fans of the 90s masterpiece that was Clueless.
