15 Movies To Watch If You Loved Clueless (2024)

DidCluelessreally turn 25 in 2020? As if! Believe it or not, Amy Heckerling's classic teen film was released all the way back in 1995. A modern-day take on Jane Austen'sEmma,Cluelessfinds hyper-privileged yetgood-intentioned teen Cher Horowitz playing matchmaker and makeover artist to her friends and teachers, only to realize the person she needs to work on is herself.

RELATED: 10 "Clueless" Storylines That Were Way Ahead Of Its Time

Everyone may have beensocial-distancingonClueless' proper anniversary, July 19, and totally buggin' about it. So, here are 10 fun and frothy movies to escape in if you miss Cher and the gang.

Updated on September 30, 2020, by Richard Keller:Cluelesswas part of a genre that changed over the decades. Where coming-of-age movies of the 1980s profiled the gross and the sensual, ones made in the 1990s were more gentile. Such is the case with the movies on this list. Here are a few more for viewers to enjoy.

Never Been Kissed (1999)

This teen movie is not really a teen movie. It stars Drew Barrymore as 20-something journalist Josie Geller. She goes undercover at a high school for investigative research. In doing so, she undergoes a transformation.

Never Been Kissedis a coming-of-age story that happens later in life. Never popular at her own high school, Josiebecomes the "It" girl in her undercover role. To the point that the coolest guy in the school asks her to the dance. Little doeshe know thatJosie hasher eyes on one of her teachers.

Pretty in Pink (1986)

One of the quintessential John Hughes movies of the 1980s wasPretty in Pink.Like Clueless, it's about high school love and social cliques.This time around, the main character isn't involved in either of them.

Molly Ringwald stars as Andie. She and her best friend Duckie, played by Jon Cryer, are constantly bullied by the "rich" cliques. However, one of their members, Blaine (Andrew McCarthy), decides to ask her out and falls in love with her. Though there's a good deal of tension inPretty in Pink, everything turns out okay in the end.

Easy A (2010)

LikeClueless, this teen movie from the 21st century takes its theme from another literary classic --The Scarlet Letter.Emma Stone plays Olive, a 17-year-old who lies to her best friend to avoid going camping. The fib starts as simply a date. However, it eventually turns into something where she loses her innocence.

RELATED:Emma Stone's 10 Most Memorable Roles: Ranked From Most Quirky to Most Serious

When the high school's church club hears this, they decide to make Olive their "project." In turn, she begins to dress more provocatively and even sews an "A" onto her clothes. Eventually, things get too big for Olive, so she needs to find a way to correct everything.

Heathers (1989)

Heatherstakes the teen movie to another level.Over the years, it has become somewhat of a classic dark comedy. Winona Ryder plays Veronica, a high school student who belongs to an elite clique whereshe is the only one not named Heather. However, she has tired of their harshness and wants to go back to her nerdy roots.

Enter Christian Slater as J.D. -- a new studentready to shake things up. He certainly does when he and Veronica connect and start to eliminate the Heathers through dubious means. Though they are killed or injured, it seems viewers root more for Veronica and J.D. than the Heathers.

The Breakfast Club (1985)

The movie that established the Brat Pack as well as John Hughes' chops as a director of coming-of-age films. It is similar toCluelessin that all of the students in Saturday morning detention want to forcibly suggest changes to each other. However, what they need to do is repair themselves.

The 1985 film has an all-star cast that includes Ally Sheedy,Emilio Estevez,Anthony Michael Hall,Judd Nelson, and Molly Ringwald. Though they seem like teenage stereotypes at the beginning ofThe Breakfast Club -- Estevez as the jock, Sheedy as the emo, etc. -- they emerge from their cocoons as the movie draws to an end.

She's All That (1999)

Imagine aCluelesswhere Cher is a vapid teenage boy whoobjectifies women and the film's takeaway is that Tai is better off looking like a stereotypical hottie. That's what you get withShe's All That. The premise: Freddie Prinze, Jr.'s Zack Siler takes a bet with an even jerkier friend (Paul Walker) that he can't make resident "ugly girl" nerd Laney (Rachael Leigh Cook) into a total smoke show. Her iconic, slow-mo walk down the stairs set to "Kiss Me" provesthat he can.

Yes, She's All Thatis still a recommendation. Those looking to round-out their '90s teen movie viewing experience can't say the job is complete without checking this film off their list.

Love, Simon (2018)

For any viewer whose heart wasall kinds of toasty warm after the sweet teen romances ofClueless,Love, Simondelivers the goods in that regard.

RELATED: 10 All-Time Best Endings In Teen Films

Simon is a well-off kid— not as rich as Cher, but he's got a pretty comfortable home life— who's popular and happy, except he's too afraid to come out as gay. When he romantically connects online to a mystery fellow male student at his school, Simon is on a quest to find him, but still wants to keep his identity a secret.

While it wasn't nearly as successful asClueless,Love, Simonhas the sweetness and levity of the classic teen films of the '80s and '90s.

Uptown Girls (2003)

Cluelessfans' hearts were broken at Brittany Murphy's untimely passing. While the film was largely seen as a breakout for Alicia Silverstone, many pointed to Murphy as the true scene-stealer.

Uptown Girlsis hardly the best film in the world, but it's packed with Murphy's charm. She plays a party girl who loses her trust fund money and is forced to take a job as a nanny. In other words, picture Cher with all her pampered privilege stripped away, and you haveUptown Girls.

Booksmart (2019)

While Tai had Cher to give her a makeover, the girls inBooksmarthad to do it themselves.

RELATED: Booksmart: 10 Reasons It's Way Better Than The Average High School Movie

Hyper-studious besties Molly (Beanie Feldstein) and Amy (Kaitlyn Dever) are shocked to discover they wasted their high school years hitting the books when their hard-partying classmates got into Ivy League schools as well. The girls decide to throw their rule book out the window for a night of wild fun.

Like Cher, Molly and Amy think they know it all, only to discover they've been clueless. Also, like theCluelessprotagonist, theBooksmartgirls win the audience over with their adorable personalities.

The Crush (1993)

It's one of Hollywood's greatest mysteries why Alicia Silverstone's career never really took off afterClueless. She's got the acting chops and comedic timing to be a leading lady of the silver screen.

But that's not to sayCluelesswas her only great role. Before the hit film, Silverstone starred inThe Crush, an erotic thriller about a young teenage girl (Silverstone) who develops an unhealthy obsession with a handsome writer (Cary Elwes) who rents a room from the girl's parents.

Critics were not kind toThe Crush, but it's the perfect movie to throw on on a rainy day. Plus, it'll be a huge treat for anyCluelessfan to contrast Silverstone's very different performances.

Fast Times At Ridgemont High (1982)

Back in the '80s and '90s, it looked like budding filmmaker Amy Heckerling was poised to be the next John Hughes. Prior to Clueless, Heckerling burst onto the Hollywood scene with her directorial debut,Fast Times at Ridgemont High.

The film is a year in the life of students at the titular high school. Though most remember Sean Penn as stoner-slacker Jeff Spicoli, the movie belongs to Jennifer Jason Leigh's Stacy. One only wishes Stacy had Cher by her side to help her find a boy she deserved. Almost 40 years later,Fast Timesviewers will never forgive Damone.

Like with Silverstone, it is shocking that Heckerling isn't a bigger name in Hollywood today. The director truly captures the teen voice in an entertaining way.

Legally Blonde (2001)

What would a movie look like with Cher in the Tai spot as the fish out of water? It would look a lot like Elle Woods' (Reese Witherspoon) experience inLegally Blonde.

The comedy finds the sweetheart sorority girl heartbroken when her boyfriend Warner (Matthew Davis) breaks up with her to find someone more "serious." To prove she's marriage material, Elle follows him to law school at Harvard, only to find herself the butt of jokes from classmates and professors alike. This galvanizes Elle to become a force to be reckoned with, learning a lot about her capabilities along the way.

Legally Blondemade a total A-list celebrity out of Witherspoon, giving her the career many thought was coming Silverstone's way afterClueless. Both films are feel-good stories about sweet yet sassy California girls that are worth checking out.

10 Things I Hate About You (1999)

WhileCluelessis the '90s teen version of a Jane Austen novel,10 Things I Hate About Youtackles Shakespeare'sThe Taming of the Shrew.

RELATED:10 Teen Dramas To Watch If You Liked The Half Of It

This movie is a veritable whos-who of young talent, with star-making performances from Julia Stiles, Heath Ledger, and Joseph Gordon Levitt, among others. The mainplot finds Cameron (Levitt) hatching an elaborate scheme to match bad boy Patrick (Ledger) with the icy Kat (Stiles) to be able to date Kat's sister (Larisa Olyenik).

Classic literature roots, ill-advised matchmaking— what more could aCluelessfan want?

Emma (2020)

Cluelesswas praised for being such a fresh interpretation of the overly-saturated sub-genre of Jane Austen adaptations.

WhenEmmahit the big screen earlier this year, many people were thinking, "Do we really needanotherone?" Turns out the answer is a resounding yes. The film follows the titular heroine (Anya Taylor-Joy) whosometimes adorably, sometimes obnoxiously meddles in the love lives of her friends, with amusing yet failing results.

A large part of what makes this recent addition to the Austen oeuvre such a success isTaylor-Joy's performance. Much like Cher, in the wrong hands, Emma could come across as a spoiled brat. Though Taylor-Joy isn't afraid to lean into Emma's unlikability, she's still a delight to watch.

Mean Girls (2004)

If you envisionCluelessthrough Tai's perspective and make Cher a million times more evil, the result isMean Girls.

After being home-schooled for most of her life, Cady Heron (Lindsay Lohan) gets her first taste of American high school. Cady is recruited by two outcasts (Lizzy Caplan and Daniel Franzese) to take down the wicked queen bee, Regina George (Rachel McAdams). But things take a turn when Cady becomes a mean girl herself

Cluelesswas a smash-hit among Gen-X teens, and is still quotable to this day.Mean Girlsdid the same for the millennial generation. That is so fetch!

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