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Movies Like Clueless You Need To Watch Next

Who doesn't love Clueless? The 1995 teen comedy, written and directed by Amy Heckerling (Fast Times at Ridgemont High), stars a charming Alicia Silverstone in her breakthrough role as the equally charismatic Cher Horowitz, a popular teen with a penchant for matchmaking. 

The film is an updated take on the 1815 novel, Emma, by Jane Austen and was among the first '90s teen films to pull from classic literature for their premises. The setting of a Beverly Hills high school turned out to be perfect for the themes of Emma and Clueless pulled off the adaptation with near flawlessness — with help from a stellar cast which included early career performances from the likes of Brittany Murphy, Paul Rudd and Donald Faison, alongside Heckerling's sharp writing and direction. The Ringer has gone so far as to call it "the best Jane Austen adaptation" — and yes, that includes 2005's Pride and Prejudice starring Keira Knightley and 1995's Sense & Sensibility starring Emma Thompson and Kate Winslet. High praise, indeed.

If you haven't seen Clueless, well, first and foremost, you need to check out the beloved teen film. But, if Clueless has captured your heart and you'd love to watch something similar, here's a breakdown of where you can start.

10 Things I Hate About You (1999)

The formula of adapting a classic literary work for teen audiences worked so well with Clueless that the trend continued for years after the film's box office dominance. In 1999, Shakespeare's comedy play Taming of the Shrew (from the 1590s!) was adapted into the modern teen romantic comedy 10 Things I Hate About You by writers Karen McCullah and Kirsten Smith and directed by TV veteran Gil Junger (Ellen, Dharma & Greg).

The film's plot follows the Stratford sisters, feminist outsider Kat (Julia Stiles) and popular girl Bianca (Larisa Oleynik), whose strict father has a rule set in place that Bianca can't date unless Kat also does. When new student Cameron, instantly smitten with Bianca, finds out about the rule, he comes up with a plan to pay the school bad boy Patrick (Heath Ledger) to pursue Kat so that Cameron can date her sister. When Patrick develops real feelings for Kat, the whole predicament gets even messier than it was to begin with.

Much like Clueless, using a classic for the foundation of a contemporary story works here, with the general themes and characters used to give nuance to a high school-set story. On the concept of pulling from the famous tale, AV Club writes, "Quirky, inventive, and brimming over with clever visual gags and colorful supporting characters, 10 Things uses Shakespeare as a jumping-off point to playfully send up a society that doesn't know what to do with a strong woman." This clever endeavor is only heightened by the stellar cast, with Stiles and Ledger leading the pack and fully cementing the film's timelessness.

She's the Man (2006)

The Bard's work proved a compelling scaffolding yet again with 2006's She's the Man, which is based on his early 17th century work, Twelfth Night — it was even written by the 10 Things screenwriting team of McCullah and Smith. 

Directed by Andy Fickman, She's the Man stars Amanda Bynes as Viola Hastings, a soccer-loving teen who starts at a new boarding school disguised as her brother Sebastian (James Kirk), in order to play for their soccer team after her own school cuts the girls' team. Viola ends up rooming with fellow soccer player Duke Orsino (Channing Tatum), whom she quickly develops a crush on. But, Duke has a thing for Olivia (Laura Ramsey) and wants "Sebastian" to help him ask her out — but Olivia has her sights set on dating "Sebastian."

The entanglement of who wants who, with the classic woman-in-disguise trope borrowed from Shakespeare, makes for a film full of hilarious mishaps. While She's the Man is definitely more beloved by audiences than critics (on Rotten Tomatoes, the Tomatometer score is just 43%, while the audience score is significantly higher at 79%) it makes for a fun watch, if not a perfect one. 

The critics who did like it upon the film's 2006 release, however, all pointed to Bynes as the driving force. TV Guide wrote that Bynes was "charming enough to carry the whole film on her shoulders," while BBC.com declared that Bynes played the part with "gusto." Supported by the rest of the talented cast, and the wit in the writing, Bynes's command of the leading woman — and man — role is worth the watch.

Easy A (2010)

If anything, Easy A gave us Emma Stone's first leading role — although it has plenty of strengths beyond that. Directed by Will Gluck (Fired Up!) and written by Bert V. Royal, Easy A isn't so much based on a classic work as it is inspired by and pays homage to Nathaniel Hawthorne's The Scarlet Letter. 

It all starts when Olive Penderghast (Stone) lies to her best friend Rhiannon (Aly Michalka) to get out of a camping trip with Rhiannon and her family; she says she has a date when really she's just planning on staying home. After the weekend, while lying about how the date went, Olive ends up insinuating to Rhiannon that she lost her virginity. This conversation is overheard, and spreads throughout the whole school. 

Soon after, Olive helps her gay friend Brandon (Dan Byrd) by pretending to have sex with him so that his sexuality doesn't become gossip. From there, Olive ends up getting paid by various boys at the school to pretend that they've had sex — and her reputation quickly becomes an infamous one.

The Guardian praised the film's ties to a classic work, writing, "The script shrewdly boosts its IQ by working in parallels to Nathaniel Hawthorne's The Scarlet Letter and piling on 80s teen movie references." Naturally, Stone was on the receiving end of much of the film's praise, as this early film in her career showed hints at the future Oscar winner developing the charms that would make her a star.

Fittingly, Empire Magazine wrote of Easy A: "Arguably the best teen comedy since Clueless, it's easy to give this one an A."

Fast Times at Ridgemont High (1982)

Heckerling's first foray into the realm of cliquey high schools was this coming-of-age-hit that introduced much of the world to still-household names like Sean Penn, Nicolas Cage and Jennifer Jason Leigh. In many ways, there never would have been a Clueless if not for the writer-director's success on Fast Times, written by Cameron Crowe (Almost Famous) who actually went undercover at a real high school for research.

The film follows a group of high schoolers at the titular high school as they navigate relationships and other school problems over the course of the year. Characters within the ensemble include Stacy Hamilton (Leigh), an inexperienced sophomore looking to rapidly gain dating experience, and Jeff Spicoli (Penn), a stoner who constantly butts heads with his history teacher Mr. Hand (Ray Walston).

While some of the jokes or scenes haven't aged particularly well — the sex scenes, for example, portray consent that is murky at best — it also presents a thoughtfulness to some sensitive topics, such as abortion. In fact, its sincere handling of the topic is what Crowe has said he's "happiest" about regarding the film, looking back on it several years later (via Variety). Furthermore, Crowe attributes the success of addressing abortion directly to Heckerling. 

With all this in mind, Fast Times is worth a watch to see these topics and themes within the realm of their time period — and to see the many ways in which the film does hold up.

Legally Blonde (2001)

Cher, the protagonist of Clueless, is often underestimated as a seemingly ditzy blonde with a passion for cute clothes and shopping. But she proves smarter than she appears to be, full of depth and insight that only grows throughout the film. 

Something similar can be said about the protagonist of 2001's Legally Blonde, Elle Woods (Reese Witherspoon): she's also blonde, cares immensely about her appearance and is just as underestimated by those around her. Further, the character of Elle and the Legally Blonde script was also written by the dream team behind 10 Things and She's the Man, Karen McCullah and Kirsten Smith (based on the book of the same name by Amanda Brown), fully cementing the film's place on this list.

At the start of Legally Blonde, directed by Robert Luketic (Monster-in-Law), fashion major Elle thinks that her boyfriend Warner (Matthew Davis) is about to propose to her. Instead, Warner dumps Elle, saying that he needs to find a serious — and smart — girlfriend while he's at Harvard Law School and that Elle just doesn't fit the bill. Elle decides to win Warner back by getting into Harvard law and becoming the serious woman he says he wants. While there, she discovers she has a knack for the law — and is too good for Warner, after all.

Delivering a message that women can be anything they want to be, but that she doesn't have to downplay her femininity or who she is to do so, there's a reason Elle has been declared a "feminist hero" on more than one occasion — for example, both Harper's Bazaar and Den of Geek have extensive pieces written about Elle's high feminist worth.

Vamps (2012)

In 2012, Heckerling re-teamed with Silverstone for the comedy horror Vamps. Pairing Silverstone with future Jessica Jones star Krysten Ritter, the two play best friends who also happen to be vampires. Their blood-sucking worlds are turned upside down when Goody (Silverstone) runs into her long lost love, Danny (Richard Lewis), while Stacy (Ritter) falls for the son of a vampire hunter, Joey (Dan Stevens).

Vamps would definitely be considered far inferior to what is Heckerling's magnum opus Clueless — the former has just a 56% Tomatometer with a 33% audience score — but is an entertaining watch nonetheless, if anything to see two charismatic leads having fun with these zany parts. Plus, Time Out said it had "much of the wit" of Heckerling's Clueless script.

All in all, the film may be "a bit of a mess," Movie Talk wrote upon its release, but it's still "worth sinking your teeth into." IndieWire summed it up thusly: "Vamps teeters on the brink of not quite working, and yet still routinely lands its laughs."

Pretty in Pink (1986)

A major part of Cher's journey in Clueless is overcoming her preconceived notions about high school cliques. At first averse to her new friend Tai (Brittany Murphy) dating outside of their popular group, she eventually realizes that if it's what makes Tai happy, the invisible boundary lines of cliques don't actually matter much. The hesitance to intertwine cliques also makes up the foundation of Pretty in Pink, the 1986 teen classic from beloved writer-director John Hughes.

In Pretty in Pink, Molly Ringwald stars as Andie, an outsider at her school whose only friends consist of fellow outcast Duckie (Jon Cryer) and her older boss Iona (Andie Boss) at the music store where Andie works. When popular kid Blane (Andrew McCarthy) asks Andie out, she's ecstatic. However, their different social circles — and varying class statuses — causes their relationship to be more of a challenge than anticipated.

Like many of the films on this list, the biggest strength of Pretty in Pink lies in its lead female character, played with iconic precision by Ringwald. Time Out declared upon the film's release that its success was due to "Hughes' skill with narrative, and to Ringwald's magnetism as a performer." Overall the film may have its flaws — in line with what decades' worth of new perspective will do to a film — but Box Office Prophets, in a retrospective examination piece from 2021, claims that the "fond memories of Pretty in Pink were genuinely earned."

Mean Girls (2004)

Speaking of cliques, 2004's Mean Girls may have a thing or two to say on the subject. Written by Tina Fey and directed by Mark Waters (The House of Yes), Mean Girls gives us Cady Heron (Lindsay Lohan), a teenager who moves with her parents from Africa, where her parents were doing scientific research, to the suburbs of Illinois. 

Completely unaware of the inner workings of an American high school, Cady finds herself thrown into the world of cliques and the popularity hierarchy, observing and navigating it like a zoologist in the wild. After befriending school outcasts Janis (Lizzy Caplan) and Damian (Daniel Franzese), Cady is also welcomed into the ranks of the school's mean girls, known as "The Plastics." What begins as a fake friendship on Cady's part to spy on the mean girls quickly turns into a genuine desire to become one of the Plastics.

A movie filled with just as many quotable lines as Clueless, the writing is sharp, clever and hilarious. The strength of the script is only heightened by the talented cast, including early career performances for now-familiar faces such as Amanda Seyfriend and Caplan and hilarious supporting roles from the likes of Amy Poehler and Fey herself. Plus, Rachel McAdams as the lead Plastic Regina George is unforgettable.

At the time of its release, The Film File wrote in its review that Mean Girls could become "a new classic of the teen genre" — and there's really no argument that it has.

Confessions of a Shopaholic (2009)

The protagonist of Confessions of a Shopaholic, Becky Bloomwood (Isla Fisher), also has a lot in common with Cher: both are typically dressed in colorful outfits, probably wearing heels, and frequently with a shopping bag in hand. The entire film of Confessions seems like it could be a look into Cher's future, in fact, one in which she's a bit older and living life on her own.

Fisher is charming as Becky, a shopping addict who finds herself drowning in debt from her expensive habit and in need of changing her overall lifestyle to become more responsible. Simultaneously, she has an interview for her dream job, writing for a fashion magazine. At the interview, she's told the position has been filled, but is offered one at another magazine owned by the same company, which could eventually lead to a job at the fashion publication. The secondary job, which Becky takes, is ironically for a magazine called Successful Saving. Keeping the truth about her massive debt from her new employer, Becky finds success with her new column, but is being weighed down by her secret.

The teetering-on-frivolous premise makes for a fun and engaging watch with (much like many of the others on this list) more depth than you may initially expect. Behind the Lens writes that the film "will make you laugh. It will make you cry. It will make you glad those credit card bills are Becky Bloomwood's and not yours."

The Edge of Seventeen (2016)

Nadine Franklin (Hailee Steinfeld), the central character of The Edge of Seventeen, may not have much in common with Cher on the surface, but both have a similar plight in that they must navigate the complicated emotions of being a teen girl — from embarrassment to jealousy, and so much more. 

Written and directed by "Post Grad" scribe Kelly Fremon Craig, The Edge of Seventeen introduces awkward high school junior Nadine, who finds herself feeling even more like an outsider when her best — and only — friend Krista (Haley Lu Richardson) begins dating her popular jock older brother Darian (Blake Jenner). Forced to deal with her own dating woes alone — ranging from the unexpected attention of a sweet classmate to accidentally sending a blunt text to her longtime crush — Nadine confides in one of her teachers, the sarcastic and cynical Mr. Bruner (Woody Harrelson).

The film has been praised up and down the board, even gaining comparisons to John Hughes, which Cultress declared is because it was "destined to be a classic teens will look to for solace." Further, considering Nadine feels so alone for most of the film, a strong performance from its star was beyond necessary — and Steinfeld delivered. The Sydney Morning Herald wrote upon the film's release: "Steinfeld begins her performance at [a] fever pitch, then cranks it up. It's an astonishing high-wire act, one of the most sustained and perceptive and complete performances I've seen in years." 

Her performance, along with the film as a whole, are bound to stick with you long after watching — much like Clueless, which we're all still talking about several decades later.

Emma (1996) and Emma. (2020)

Of course, we have to recommend a few straightforward adaptations of Jane Austen's Emma, the source material for Clueless

Those typically watching the Alicia Silverstone classic don't have comparisons to Austen on the mind, so it's worthwhile to watch either the Emma adaptation from 1996 (with Gwyneth Paltrow) or the one from 2020 (with Anya Taylor-Joy) afterwards to see the similar strings being dangled. Of course, they're also worth watching because they're really good movies.

In the 1996 version, directed and adapted by Douglas McGrath (Infamous), Paltrow takes on the titular role in a performance that the New York Times said was filled with "elegance and patrician wit that bring the young Katharine Hepburn to mind." In 2020, the same title was given a period, and the role was taken on by Queen's Gambit star Anya Taylor-Joy, who received ample praise for her performance. The Guardian wrote that "Taylor-Joy creates an admirably spiky character who is less likable than some of her screen predecessors, and all the better for it."

in the end, Austen's wonderfully keen satire — present and active in Clueless — never goes out of fashion.