If you’re a fan of the classic 90s teen comedy Clueless, you’re not alone. This iconic film, loosely based on Jane Austen’s Emma, follows the misadventures of wealthy, popular, and fashionable high school student Cher Horowitz as she plays matchmaker, makes over a new girl at school, and eventually realizes she has some growing up to do herself. With its clever writing, memorable characters, enviable fashions, and endlessly quotable lines (“As if!”), Clueless captured the spirit of the 90s teen experience and has remained a beloved favorite for over 25 years.
But what should you watch when you’ve seen Clueless so many times you can recite it by heart? Never fear – there are plenty of other smart, funny, and heartfelt teen comedies out there to satisfy your craving. Here are 17 movies to add to your watch list if you love Clueless:
1. Mean Girls (2004)
You can’t talk about great teen comedies without mentioning Mean Girls. Written by Tina Fey and starring Lindsay Lohan, Rachel McAdams, Amanda Seyfried, and Lacey Chabert, this movie follows Cady, a formerly homeschooled 16-year-old, as she navigates the treacherous social hierarchy of high school and the infamous clique known as “The Plastics.”
Like Clueless, Mean Girls is endlessly quotable (“On Wednesdays we wear pink!”), wickedly funny in its satirization of high school life, and ultimately carries a positive message about being true to yourself. It’s the perfect choice when you want a movie that will make you laugh out loud.
2. Legally Blonde (2001)
In this comedy, Reese Witherspoon stars as Elle Woods, a bubbly sorority girl who decides to follow her ex-boyfriend to Harvard Law School to win him back. Everyone underestimates the seemingly ditzy blonde, but Elle proves she’s smarter than anyone realized as she not only succeeds in her classes but solves an important legal case.
Like Cher in Clueless, Elle has a passion for fashion and a sunny personality that charms almost everyone she meets. Legally Blonde is a feel-good movie with a feminist message about not judging a book by its cover. If you love watching Cher take on a makeover project, you’ll enjoy seeing Elle transform from a Malibu Barbie to a brilliant legal mind.
3. Easy A (2010)
This clever comedy puts a modern twist on Nathaniel Hawthorne’s The Scarlet Letter. After a little white lie about losing her virginity gets out, clean-cut high school student Olive (Emma Stone) decides to embrace her new “slutty” reputation. She even starts wearing a red “A” on her clothes in reference to Hawthorne’s novel.
Like Clueless, Easy A is full of literary references and witty dialogue. It also deals with themes of gossip, reputation, and female sexuality in a smart and humorous way. Stone shines as the quick-witted Olive, and the supporting cast includes Stanley Tucci, Patricia Clarkson, and Lisa Kudrow. If you like the way Clueless put a satirical, contemporary spin on a classic story, you’ll appreciate Easy A.
4. She’s All That (1999)
One of the most iconic teen romances of the 90s, She’s All That stars Freddie Prinze Jr. as Zack, a popular jock who makes a bet that he can turn any girl into the prom queen. He sets his sights on Laney (Rachael Leigh Cook), a shy, artistic outcast. As he gives her a makeover and draws her out of her shell, Zack starts to fall for the girl he thought was beneath his notice.
Clueless fans will recognize the parallels to Cher giving Tai a makeover and setting her up with Elton. She’s All That follows a lot of classic teen movie tropes, but it does it well, with a charming cast and some sweet moments. Plus, there’s an iconic prom entrance and dance scene set to Sixpence None the Richer’s “Kiss Me” that will give you all the nostalgic feels.
5. 10 Things I Hate About You (1999)
Clueless isn’t the only great 90s teen movie inspired by classic literature. 10 Things I Hate About You reimagines Shakespeare’s The Taming of the Shrew in a 1990s high school setting. Julia Stiles stars as Kat, an intelligent, opinionated senior who doesn’t care what anyone thinks of her. Heath Ledger plays Patrick, the school rebel who is paid to try to win Kat over so that her popular younger sister Bianca (Larisa Oleynik) will be allowed to date.
With its sharp, sarcastic dialogue and use of Shakespearean plot devices, 10 Things I Hate About You should definitely appeal to Clueless fans. Kat is like a more acerbic, rebellious version of Cher, and watching her and Patrick match wits and eventually fall for each other is a delight. The movie also features a young Joseph Gordon-Levitt in a breakout role.
6. Heathers (1989)
Darker and edgier than Clueless, this cult classic stars Winona Ryder as Veronica, part of a popular but cruel clique of girls all named Heather. When Veronica and her new boyfriend, rebellious outsider J.D. (Christian Slater) accidentally poison the leader of the Heathers, they make it look like a suicide, setting off a string of copycat attempts. As the body count rises, Veronica realizes J.D. is more dangerous than she thought.
Heathers is a pitch-black comedy that satirizes the high school social hierarchy and the pressure to conform. Like Clueless, it features over-the-top characters, memorable fashions, and infinitely quotable dialogue (“What’s your damage, Heather?”). But it takes the cutthroat world of high school popularity to much darker extremes. If you like Clueless but wish it had more of an edge, Heathers is the movie for you.
7. Bring It On (2000)
This cheerleading comedy stars Kirsten Dunst as Torrance, the newly elected captain of the Toros cheer squad. When she discovers that their championship-winning routines were stolen from an inner-city squad, the Clovers, Torrance has to come up with all new material and lead her team to victory at Nationals.
Like Clueless, Bring It On has a fluffy, fun exterior, with a lot of memorable cheers and catchy songs. But it also touches on more serious themes of race and class as the wealthy, mostly white Toros have to confront their privilege. The dynamic between Torrance and Isis (Gabrielle Union), the head of the Clovers, brings some welcome depth to the story. If you enjoy the “fish out of water” scenes of Cher in Tai’s grungy world, you’ll appreciate the culture clash in Bring It On.
8. Romy and Michele’s High School Reunion (1997)
While not strictly a teen movie, since it’s about 28-year-old women, this comedy taps into the same nostalgic vein as Clueless. Romy (Mira Sorvino) and Michele (Lisa Kudrow) are two inseparable best friends determined to impress their former classmates at their 10-year high school reunion. The only problem is, they haven’t done much with their lives since graduation. So they decide to fake it, pretending to be successful businesswomen.
Romy and Michele has the same sweet-but-silly tone as Clueless, and the flashback scenes to Romy and Michele as ’80s high schoolers definitely capture the same satirical spirit. The heart of the movie is the friendship between the two women, which will remind you of Cher and Dionne. If you’ve ever felt like you had some growing up to do or wanted to reinvent yourself, you’ll relate to Romy and Michele’s journey.
9. The Edge of Seventeen (2016)
This coming-of-age comedy-drama stars Hailee Steinfeld as Nadine, an awkward 17-year-old outcast whose only friend starts dating her popular older brother. Feeling more alone than ever, Nadine struggles to figure out who she is and where she belongs.
While The Edge of Seventeen has a lot more angst than Clueless, it shares a lot of the same DNA, with a smart, sympathetic teen heroine at its center. Nadine is like the flipside of Cher – just as stubborn and sure of herself, but deeply insecure and often her own worst enemy. Watching her navigate the ups and downs of adolescence and learn to open up to others is poignant and relatable. If you want a teen movie with a little more grit and emotional depth, give this one a try.
10. Jawbreaker (1999)
Another pitch-black comedy in the same vein as Heathers, Jawbreaker follows a popular clique who accidentally kill their leader, then plot to cover it up and make over a nerdy witness, Fern (Judy Greer), to take her place. Things quickly spiral out of control as former outcast Fern, now remade as glamorous Vylette, becomes drunk on her newfound power and popularity.
Like Clueless, Jawbreaker is full of colorful fashions and quotable one-liners (“Learn it. Live it. Love it.”). But this movie cranks up the cruelty and cattiness to deliriously campy levels. It’s not as clever as Clueless, but it’s a wild, stylish ride with a trio of pitch-perfect mean girl performances from Rose McGowan, Julie Benz and Rebecca Gayheart. If you ever wished Clueless took place in a more heightened, amoral universe, Jawbreaker is for you.
11. Never Been Kissed (1999)
Drew Barrymore stars in this rom-com as Josie, a 25-year-old copy editor who goes undercover as a high school student for a story. Having been a nerdy outcast in her real high school days, Josie is determined to have the full teenage experience she never got to enjoy, including her first kiss. But she soon finds herself falling for her English teacher (Michael Vartan).
Never Been Kissed is sweeter and more romantic than Clueless, but it taps into the same nostalgia for the teen experience. Josie may be an adult, but she’s just as clueless as Cher when it comes to navigating high school hierarchies and relationships. Watching her get a second chance at adolescence is wish fulfillment with a lot of heart. If you like the way Clueless finds the humor and heart in teen life, Never Been Kissed delivers that in spades.
12. The Duff (2015)
In this comedy based on the novel by Kody Keplinger, Bianca (Mae Whitman) is a happy, confident high school senior – until she finds out that her classmates secretly know her as the DUFF (Designated Ugly Fat Friend) of her more popular besties. Hurt and angry, she enlists the help of a charming jock (Robbie Amell) to give her a makeover.
The DUFF has a lot in common with She’s All That, but with a more empowering message for its heroine. While there is a makeover, the real transformation is in how Bianca sees herself. The movie does a good job of depicting the very real insecurities and pressures teenage girls face while still being fun and funny. If you like Clueless for how it handles the highs and lows of female friendships, The DUFF is definitely worth a watch.
13. To All the Boys I’ve Loved Before (2018)
Based on the hit YA novel by Jenny Han, this Netflix romcom follows Lara Jean (Lana Condor), a shy 16-year-old who writes secret love letters to her crushes that are never meant to be sent. When the letters accidentally get mailed out, she finds herself in a pretend relationship with one of the recipients, Peter (Noah Centineo), to cover up her true feelings for her sister’s ex-boyfriend.
To All the Boys has the same warm, fuzzy feeling as Clueless, with a lot of heart and humor as Lara Jean comes out of her shell and takes risks in love and life. The fake dating setup also has shades of the matchmaking hijinks in Clueless. But the real strength is the sweet, sparky chemistry between Condor and Centineo. If you’re a sucker for a good teen romance with all the feels, you need to queue this one up ASAP.
14. The Craft (1996)
When new girl Sarah (Robin Tunney) falls in with a trio of outcast teenage girls who practice witchcraft, she’s excited to find friends and a way to get power in her life. But as they start casting spells on their classmates and enemies, things take a dark turn, and Sarah realizes her new coven may be more dangerous than she thought.
The Craft isn’t a comedy like Clueless, but it shares some DNA in its depiction of teen girl power dynamics and the desire to fit in and be accepted. There’s also a strong fashion element, with the four leads sporting some delightfully witchy ’90s goth looks. If you like Clueless but wish it had a more supernatural bent, The Craft delivers some spooky, stylish fun.
15. Booksmart (2019)
On the eve of graduation, two academic overachievers, Amy (Kaitlyn Dever) and Molly (Beanie Feldstein), realize they’ve missed out on a lot of typical high school fun and hijinks. Determined to make up for lost time, they set out to cram four years of partying into one epic night.
Booksmart has a lot in common with Clueless in its witty, pop-culture-savvy dialogue and depiction of female friendship. Amy and Molly’s relationship is the heart of the movie, and their banter and misadventures are a blast to watch. There’s also some interesting commentary on class and privilege, with the girls having to confront their assumptions about their classmates. If you want to see a fresh, funny take on the “one crazy night” teen comedy formula, Booksmart is a must-see.
16. Cruel Intentions (1999)
A deliciously campy modern update of the French novel Les Liaisons dangereuses, Cruel Intentions follows a pair of wealthy, manipulative step-siblings, Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillippe), as they make a wager over whether Sebastian can seduce and ruin the new headmaster’s virginal daughter, Annette (Reese Witherspoon). But the game gets more complicated as Sebastian starts to develop real feelings for Annette.
Cruel Intentions is a lot darker and more sexually charged than Clueless, but it’s got the same sharp, satirical bite in its depiction of bored, privileged teens behaving badly. Gellar is deliciously wicked as Kathryn, and Witherspoon shows some of the same plucky charm that made her so winning in Legally Blonde. If you like Clueless but want something a little more risqué, Cruel Intentions is a wild, sexy ride.
17. Saved! (2004)
This satirical comedy follows Mary (Jena Malone), a devout Christian teenager who gets pregnant after having sex with her gay boyfriend in an attempt to “cure” him. Ostracized by her judgmental classmates and questioning her faith, Mary finds solace in a group of other misfits, including a rebellious Jewish girl (Eva Amurri) and the school’s only openly gay student (Macaulay Culkin).
Like Clueless, Saved! takes on the social hierarchies and hypocrisies of a specific teenage milieu with wit and insight. It’s got a sharper, more biting sense of humor, but there’s also a lot of heart in its depiction of outcasts finding strength in each other. If you appreciate the way Clueless finds the humor in the high school experience while still having something to say, Saved! is definitely worth checking out.
So there you have it – a mix of 90s nostalgia fests, snarky satires, and spirited comedies to satisfy any Clueless fan. Whether you’re in the mood for a fun makeover story, a biting look at popularity, or a fierce, fashionable heroine, these movies deliver. Time to put on your favorite plaid outfit, grab some snacks, and have a movie marathon!
