Marking 25 years of Clueless, the teen comedy that keeps on giving 

Twenty-five years on, why does a low-budget teen comedy, based on a 200-year-old novel, continue to resonate with audiences? 
Marking 25 years of Clueless, the teen comedy that keeps on giving 
Alicia Silverstone in Clueless

Imagine a world without Jane Austen. It’s a frightening prospect, isn’t it? No Austen means no Mr Darcy, no Dashwood sisters and no Emma Woodhouse. We’d have been deprived of some of the greatest works of literature ever produced. Worse still, there would be no Clueless.

Back in the early nineties, writer and director, Amy Heckerling – chief in command of such divisive, mainstream comedy features as Fast Times at Ridgemont High and Look Who’s Talking – took a meeting with the suits at Fox. Indeed, the money men had wanted Ms Heckerling to develop a teen-orientated television show. They’d wanted something fresh, something exciting – something about “the ‘in’ crowd”.

Heckerling, though initially reluctant, agreed under one condition. She’d give Fox their show about teenagers, so long as she could “make fun of them”. A deal was set, and Heckerling went to work, devising a pilot about a girl “that was completely happy, no matter what happened.” It was only months later, after Fox had passed on her script, that Heckerling realised what she’d done.

She had created a fictional character whose ideals and idiosyncrasies were almost identical to that of one of literature’s most beloved protagonists. She had inadvertently taken inspiration from one of her favourite novels. Basically, Heckerling had written her own Emma, and she hadn’t developed a television pilot - she’d plotted a big-screen feature.

Better still, Heckerling kept on going, swapping the salubrious, period postcard setting of Austen’s 19th century novel, alongside its upper-class ensemble of corset-wearing caricatures, for a gang of self-obsessed, teenage brats in 20th century Beverly Hills. The scene was set for a contemporary remix like no other.

The script (initially titled No Worries, and later, I Was a Teenage Teenager) was eventually picked up by Paramount, after the fools at Fox had unsuccessfully demanded that Heckerling write more male characters. A date for production was finalised. On July 19 1995, Clueless was released in cinemas to critical and commercial acclaim. The rest is history.

Twenty-five years on, how is it that a low-budget teen comedy, based on a 200-year-old novel, continues to resonate with audiences? What is it about this remarkable picture that sets it apart from the rest?

You know the gist. Alicia Silverstone stars as Cher Horowitz, the 16-year-old Emma of the piece and the most popular, most well-off girl at Bronson Alcott High School. Her widower father is a lawyer.

They live in a mansion. Her annoying, ex-stepbrother, Josh (the brilliant Paul Rudd), is a constant thorn in her side.

Cher, bless her heart, lives for fashion, partying and romance, and she and her best friend, Dionne (Stacey Dash), love nothing more than toying with other people’s love lives. Throw in a sensational array of outfits (there are a lot of plaid skirts in here) and a splattering of sublime one-liners (“She’s my friend because we both know what it’s like for people to be jealous of us”), and you’ve got yourself something special.

Heckerling’s delightful joint – one-part ingenious satire, two-parts heart-on-sleeve rom-com - exists entirely in a world of its own creation. Running riot in a fabulous, fairy tale depiction of Los Angeles County’s most famous city, Clueless is almost as enthralled as we are by its inhabitants. It embraces its absurdities. It isn’t afraid to poke fun at itself. But there is a warmth and sweetness to its delivery.

At its core, Clueless is really a story about self-expression, and that’s what makes it so relatable. Cher and her comrades may be filthy rich, but they’re just like you and me. Their actions have consequences. Cher eventually learns that the heart doesn’t always get what it wants. She and her friends are bound by trends and by inane social codes and constructs. Everyone, at some point in their life, realises that Paul Rudd is, in fact, the perfect man for them.

Casting was key. Indeed, Ms Heckerling and her team had been the first to realise that there was more to Ms Silverstone than trashy MTV thrillers and Aerosmith videos. There were other candidates for the part of Cher, including Reese Witherspoon and Sarah Michelle Gellar, but Silverstone stood out. Heckerling saw a touch of Marilyn Monroe in her leading actress - a “pretty, sweet blonde who, in spite of being the American ideal, people still really like".

Indeed, Silverstone dug deep, crafting a smart, funny and sympathetic character out of Cher - someone who’d eventually learn from her mistakes, and someone we could root for, even at her worst. And, really, isn’t that the point of Emma? She was in good company. Stacey Dash steals scenes with a single look. 

The poster for the 1990s teen hit.
The poster for the 1990s teen hit.

Brittany Murphy goes above and beyond as giddy newcomer, Tai. They would all go on to have successful careers on the stage and screen. Silverstone would sign a multi-million-dollar deal with Columbia Pictures (she’d later play Batgirl in Joel Schumacher’s Batman & Robin). Murphy, meanwhile, enjoyed a series of well-received supporting roles in Girl, Interrupted, 8 Mile and Sin City. She died of pneumonia in December 2009, aged 32.

Incidentally, Clueless also had an unintentional effect on the cinematic landscape, with major studios optioning a series of flashy, contemporary high-school flicks based on classic texts. 

Think 1999’s 10 Things I Hate About You, a slick and inventive take on William Shakespeare’s The Taming of the Shrew, with Julia Stiles and Heath Ledger. Think She’s All That (1999), a Gen Y remix of George Bernard Shaw’s Pygmalion, with Freddie Prinze Jr and Rachael Leigh Cook. 

Even Cruel Intentions (another ’99 hit), got in on the act, taking its cue from Pierre Choderlos de Laclos’s 1782 novel, Les Liaisons Dangereuses.

There have been other cinematic Emmas, too. Gwyneth Paltrow, Kate Beckinsale and Anya Taylor- Joy are just some of the actresses that have walked in her shoes. Are any of them as good as Clueless? As if.

Truth be told, Heckerling’s film may be the only one that successfully managed to convey a complete understanding of both the text and tone of Austen’s masterpiece. It is a note- perfect cover version. 

It still makes us laugh. It has aged almost as well as Paul Rudd. Clueless is, like, totally the best Emma movie, and that’s a fact.

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