(Credits: Far Out / Paramount Pictures)
Tue 9 September 2025 21:45, UK
Few movies have tapped into the American high-school lexicon of the 1990s quite like Clueless. Over the course of the film, we hear phrases that teens simply don’t utter today (“I’m totally buggin’”) and it makes you wonder exactly when everything changed.
While the movie has endured due to its inherently timeless elements – like school hierarchies and the messiness of coming-of-age, from friend fall-outs to unrequited crushes – it has a pre-social media purity to it that makes you want to go back in time. Sharply-written in its depiction of rich teens whose naivety to the world could easily become tiresome, the film instead endears itself to viewers with its quotable lines, unforgettable outfits, and self-awareness.
Amy Heckerling’s film is easily one of cinema’s greatest teen movies. It’s way more than a popcorn flick to be consumed and forgotten – this is a thorough examination of the modern world through the eyes of teens on the cusp of adulthood, where the pressures of social hierarchy and conforming to a certain archetype are called into question.
Clueless was released during a boom of teen movies inspired by classic novels and plays – a sensation that, as bizarre as it sounds, worked surprisingly well. There was 10 Things I Hate About You, based on Shakespeare’s The Taming of the Shrew, while She’s the Man took the Bard’s Twelfth Night and gave it a modern spin.
The slightly raunchier Cruel Intentions was a retelling of Les Liaisons dangereuses, while Romeo + Juliet, starring Leonardo DiCaprio, transplanted the classic play into a gritty American setting that appealed to younger audiences.
Which classic novel is Clueless based on?
There’s a very strong argument to have that Clueless started this trend, with the 1995 movie taking its narrative from a Jane Austen classic. There was somewhat of an Austen boom during this period, too, with Emma Thompson’s Sense and Sensibility, the BBC’s flawless Pride and Prejudice miniseries, and the television movie Persuasion emerging that same year.
Meanwhile, a movie version of Emma came in 1996, starring Gwyneth Paltrow as the titular heroine, but could that compete with Clueless?
Austen’s comedy of manners was the basis for the picture, and her witty critiques of society made for the perfect source material to explore social hierarchy and class in a ‘90s high-school setting. It’s easy to think of novels written centuries ago as stuffy and boring if you’re not familiar with them, but Austen was hilarious, and Emma is a fine demonstration of her comedic abilities.
Cher is the modern Emma, matchmaking her way through life with a strong sense of confidence in herself, something that sometimes borders on ignorance and vanity. It’s hard not to love Cher though, for while she might be spoiled, she is inherently kindhearted – just wanting the best for her friends and family.
So, let’s compare Austen’s characters and their Clueless counterparts. Cher tries to set new girl Tai up with Elton, and this reflects Emma trying to get Mr Elton to fall for Harriet. Yet, both Elton is much more interested in their respective lead, who ultimately ends up with, in the case of Emma, Mr Knightley, and in Clueless, Josh.
In the former, Emma tries to date Frank, who turns out to be secretly planning on marrying another, while the teen romcom sees Cher pursue Christian, despite him obviously being gay. Then you’ve got Clueless’ Travis, who represents Robert Martin, while Mr Hall appears to be a version of Mr Weston.
Austen’s stories still resonate with readers all these years later because they observe society so astutely and humorously, so it’s no wonder that Emma worked perfectly as the basis for Clueless.
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