As If! These 22 Movies Are Perfect For Anyone Who Loves Clueless
Clueless may be an iconic film from the '90s, but despite its age, this movie has managed to be a relevant, timeless, and just plain fun ride for any generation. Loosely based on Jane Austen's classic novel Emma, the colorful teen comedy follows the antics of Cher, a rich, self-absorbed but good-hearted Beverly Hills teenager, as she tries to "improve" the lives of everyone around her. Along the way, we're treated to a fabulous parade of exaggerated '90s fashions, throwback pop music choices, and so, so much quotable dialogue.
In some ways, it's funny to look back at Clueless and see how it was clearly meant to be an over-exaggerated satire. Things like teenagers having cell phones on them at all times are treated as over-the-top jokes — and now it's just part of normal life! There's something really fun about Clueless, though, in how it plays with the usual tropes of teen movies.
Typically, the "popular" kids are the villains, and the heroine is "not like other girls." In Clueless, each of the cliques has its own minor problems, but only a couple of people are actually terrible. While Cher is very much "like other girls," she doesn't have to give that up to help further her character development.
That irrepressible joy and big heart are why Clueless has endured as a classic for decades now, and it's definitely had a big influence on teen movies of more recent years, too. While nothing could ever quite capture the exact same vibes as Clueless, there are plenty of movies out there that pair perfectly with it. If you're looking to have a double feature or just want more movies that are like Clueless, we've rounded up some of our best recommendations in the gallery ahead. How many of these are already favorites for you?
Clueless is, of course, based loosely on Jane Austen's classic novel Emma. The book — and its 1996 movie adaptation starring Gwyneth Paltrow — centers on a wealthy young woman who passes her time by trying to neatly arrange the lives of everyone around her, all while being, well, clueless to her own feelings and the effects of her meddling. This late '90s period dramedy stays mostly true to the novel with just a few cuts and condensed storylines here and there. It's a gauzy, dreamy, and (of course) romantic movie that's perfect for Clueless fans looking for more about where it all began.
The "queen bees" of Clueless's Beverly Hills high school are actually pretty nice people, just a little bit self absorbed. Heathers features a similar storyline in which unpopular Veronica (like Clueless's new student Tai) gets sucked into the dramatic dynamics of her high school's most popular, powerful group. Unlike Clueless, however, Veronica's new "friends" are mean spirited and selfish. To add insult to injury, Veronica's love interest is a charismatic rebel with a violent streak. The dark, satirical comedy takes the high school movie genre and flips it on its head, turning the usual social dynamics into deadly, serious business. In the end, it's up to Veronica to set things right.
One of the funniest — and most realistic — parts about Clueless is watching Cher slowly come to the realization that she herself has been totally clueless about how things really are outside of her little bubble. Compared to Cher, Booksmart's Molly and Amy are on the other side of the popularity spectrum, but they also have a similar epiphany. After spending their whole high school careers as studious, nerdy overachievers, the pair make a pact to let themselves go and have one wild night of partying before college. They quickly realize that many of their assumptions were way off base, but they learn a lot about themselves along the way.
Bridget Jones's Diary
Clueless is a modern-day refresh of a classic Jane Austen novel, and so is Bridget Jones's Diary, which transplants Pride and Prejudice into early 2000s London. Bridget is a bit of a mess. She's stuck in a dead-end job and has a massive crush on her unavailable, but charming, playboy boss. She's definitely not at her best when she crosses paths with family friend Mark Darcy, a well-off lawyer who she can't stand. As Bridget starts to take control of her own life and break her bad habits, she also starts to realize that maybe Mark Darcy isn't such a terrible person after all.
Just like Clueless adapts a Jane Austen novel into a contemporary high school setting, Easy A does the same with The Scarlet Letter, although it's definitely more of an allusion than a direct adaptation. Ordinary, slightly geeky Olive accidentally starts a rumor about herself while trying to get out of a trip with her friend's hippie family. When word spreads, Olive initially decides to lean into her newfound — and totally phony — scandalous reputation. After a little while, though, she starts to see the downside of being the school's "marked woman." With the help of her charming friend (and crush), she tries to find a way to set things right.
Clueless makes it very clear that Jane Austen's stories, including Emma, are actually a lot funnier than they sometimes get credit for. Autumn de Wilde's 2020 version of Emma, led by breakout star Anya Taylor-Joy, really leans into the absurd humor of it all. This version of Emma is still a slightly unlikeable, blissfully self-assured, and self-absorbed rich girl with a penchant for meddling. Emma's misguided attempts at arranging a romance for her new friend Harriet go hilariously awry, as do Emma's plans to improve herself as a person. It's the same plot you know and love but with a candy-colored visual palette and keen sense for finding the ridiculous, funny moments.
We can probably all agree that, if they ever met, Cher Horowitz and Elle Woods would definitely be friends! Instead of falling into the all-too-common "not like other girls" trope, both Cher and Elle are unabashedly glamorous, cheerful fashionistas who are also much smarter than they often get credit for. Elle starts out as a frivolous sorority girl, expecting to get engaged to her aspiring-politician boyfriend, Warner. When he dumps her instead, claiming he needs to date someone more "serious," Elle sets out to prove him wrong and get him back by getting into Harvard Law herself. Along the way, she finds both friends and enemies in unlikely places, and she starts to pursue dreams for herself, not for Warner.
While Love, Simon and Clueless don't share the same plot, they do both have that cheery and angsty atmosphere you see typically in high school teen dramas. This film is a heartfelt story that ends happily, even though there are some pretty stressful parts in the middle. Simon, like Cher, is popular and fairly happy in his life, except for one thing — he's gay and closeted. However, he starts to fall for an anonymous online pen pal, who is another gay student at their high school. Simon sets out to try to uncover his mystery guy without revealing more about himself than he's ready to.
For every '90s teen who quoted Clueless, there's a teen from the early 2000s who quoted (and still quotes) Mean Girls. Much like Clueless, it's a sharp-tongued satire of the social hierarchy of high school, although maybe one with a little more drama. This time, the newbie-outsider is Cady, a new student who's attending "real" school for the first time after being homeschooled in Africa by her zoologist parents. At first, she befriends a couple of quirky outsiders, but soon she gets drawn into the machinations of The Plastics: the too-cool, too-mean clique that rules the school. Cady hatches a plan to infiltrate and bring down the Plastics, but along the way, she starts to become a "Plastic" herself.
She's the Man
Where Clueless takes its cues from Jane Austen, the goofy teen comedy She's the Man has even loftier roots: Shakespeare! Loosely inspired by the twin-swapping, gender-twisting comedy Twelfth Night, this comedy centers on Viola, a soccer player who's angry about her team being cut. When her twin brother, Sebastian, secretly ditches his elite boarding school to run off with his band, Viola agrees to pretend to be Sebastian. Viola takes his place and hopes to prove all the naysayers wrong with her soccer skills. Along the way, she befriends Duke, the team captain, and accidentally starts a love quadrangle full of secret identities and mixed-up crushes.
Bring It On
Clueless mostly confines its high school drama to just one high school, but Bring It On takes that social hierarchy business and makes it even bigger. When a popular, elite cheer squad gets a new member, they discover that they've been inadvertently performing plagiarized routines from another cheer team — and that squad is not happy. As the two squads get ready to face off and determine who's the cheer champion once and for all, team members from both squads deal with the usual stresses of high school and worry about letting their peers down. It's a very different look at the "popular kids" than Clueless, but one that's every bit as rewatchable!
Never Been Kissed
One of the great joys of Clueless is that, even though it's about teenagers, it's one of those timeless movies you can connect with at any age. There's a touch of that in Never Been Kissed, a rom-com about adults hiding within the trappings of a teen movie. Josie, a young reporter, goes undercover at a high school to investigate a big story. At first, it's a chance for Josie, who was unpopular in high school, to get a second chance at closure for that stage in her life. Things get complicated when she develops feelings for a teacher who would be a perfect match for her — if he didn't think she was a teenage student.
Pretty in Pink
Clueless is all about the cliques and social strata of high school, plus the question of whether love (or any other kind of relationship) can ever transcend those boundaries. Pretty in Pink tackles these same questions but with a very different perspective. Instead of a wealthy "queen bee" like Cher, Pretty in Pink's heroine Andie is a quirky, artsy outsider who gets picked on by the school's rich jerks for being poor. Andie is excited when her crush on sweet, but rich, Blane is reciprocated, but neither of their respective friend circles thinks that their relationship is a good idea.
She's All That
One of the most fun things about Clueless is watching the grumpy-and-sunshine dynamic develop between perky, carefree Cher and serious, philosophical (though still snarky) Josh. Reverse the genders of that particular pairing and add all the drama of a secret-bet storyline, and you've got She's All That, a twist on My Fair Lady and Pygmalion. Popular jock Zack accepts a bet that he can turn any girl, even artsy, nerdy Laney, into a prom queen. There's plenty of humor from Zack's goofy golden-boy personality butting up against suspicious, deadpan Laney, and it's charming to watch them become friends — and then maybe even more.
10 Things I Hate About You
In case you haven't noticed, the '90s really, really liked their "classic-literature-to-teen-movie" genre. This time, it's The Taming of the Shrew that gets a modern-day update. Independent, fiercely feminist Kat couldn't be more different from her popular, perky sister Bianca. Their overprotective dad uses this to his advantage by imposing a rule: Bianca can't date until Kat does, too. When two very different guys start vying for Bianca's attention, one comes up with a plan: pay Patrick, the school's bad-boy loner, to date Kat. At first, Kat rebuffs Patrick, but in time, they start to warm up to each other. However, there's still the small matter of the true reason he asked her out in the first place.
Confessions of a Shopaholic
If Cher didn't have her character arc in high school, we can imagine she might have ended up like Becky, the shopaholic at the center of this romantic comedy. Becky's love for shopping gets completely out of hand, especially when she aims to land a dream job at a fashion magazine. Ironically enough, she winds up getting a job writing about personal finance. To her surprise (and the surprise of her slightly stuffy but well-meaning editor), her unorthodox tips and writing style make her a viral hit, and her editor is completely charmed. Unfortunately, there's still the small matter of her shopping addiction — and the debt collector doggedly tracking her down.
Clueless and Hairspray both have an enormous heart and a joyous, colorful atmosphere, all within a high school setting. Rather than an arbitrary social hierarchy, Hairspray is based on the very real situation of segregation and racism in the 1960s. Proud curvy girl Tracy auditions to be on her local afternoon dance TV show, but she's sidelined for her size and her open support of racial integration. Instead, she finds friends and allies in the Black students she meets in detention. Tracy teams up with this new group — and one of the dance show's heartthrobs — to make historic changes.
13 Going on 30
While 13 Going on 30 isn't exactly a teen movie, it has the same kind of warmhearted spirit, throwback vibes, and sweet romance that Clueless is known for. Unpopular teen Jenna makes a wish on her 13th birthday to be "thirty and flirty and thriving," then suddenly wakes up to find that her wish has come true. After discovering that her future self is successful but also selfish and shallow, Jenna tries to make things right. With the help of her middle school BFF Matt, with whom her adult self had long ago lost touch, Jenna just might be able to transform her life into something that her teenage self can be proud of, too.
The Breakfast Club
There is no movie more iconically about high school social circles than The Breakfast Club. Five students who have nothing in common ("a brain, an athlete, a basket case, a princess, and a criminal") are all stuck together in an all-day Saturday detention. At first, all five clash, but with nothing else to do, they slowly start talking and opening up to each other. As they get to know more about one another — and the incidents that landed them all in detention in the first place — they also start to question the rigid social rules that have kept them all isolated this whole time.
The Princess Diaries
Cher and Dionne loved giving Tai a makeover, but Tai is probably more receptive to her new look and status than Mia — the heroine of The Princess Diaries — at first. Mia is an "invisible" high school student whose life gets turned upside down when her estranged paternal grandmother shows up and reveals that Mia's late father was a prince, making Mia the princess and heir to the Genovian throne. Mia reluctantly attends "princess lessons" with her royal grandmother and receives a glamorous makeover, all while trying to hide the truth about her identity from everyone. When the press catches wind, Mia is suddenly very visible, but her newfound fame reveals who she can really trust.
A Cinderella Story
If you want even more of a teen romantic comedy than Clueless, try this sweet, fairy-tale-inspired flick from 2004. Sam is unpopular at her high school and forced to work at the diner owned by her image-obsessed stepmother. Her two solaces are her dreams of attending Princeton and her secret chats with an online pen pal. What Sam doesn't know is that her online crush is Austin, the golden boy at her high school. When she gets the chance to meet him in person at a school dance, she seizes the opportunity, unknowingly opening the door to what could be either disaster or freedom at last.
What a Girl Wants
One of the major plot lines in Clueless is Cher's "mentoring" of new student Tai, who is definitely a fish out of water at their elite high school. Like Tai, What A Girl Wants's Daphne finds herself unexpectedly thrown into a glossy world that she has no idea how to navigate. After graduating high school, Daphne runs away to London to try to track down her aristocratic father, who turns out to be a politician hoping to be elected prime minister. Although her father seems to welcome her into his life, others in their snobby, elitist circles aren't quite so happy about her arrival. No matter how hard she tries, she just doesn't seem to fit in, but she's a lot more tenacious than others give her credit for.