From ‘as if!’ to cultural icon: Clueless turns 30 and proves it’s more than just a pretty plaid skirt

How can it be that Clueless, a thoroughly modern social comedy, is now a period piece?

When Clueless came out in July 1995, it was fresh and exciting, an update of, at the time, a 180-year-old novel by Jane Austen. Rather than Regency England, it was 1990s Beverly Hills, and the references were Ren & Stimpy, the Bosnian War, Coolio and Cindy Crawford’s Buns of Steel.

Friends, it’s been 30 years.

Clueless and Emma may have been almost two centuries apart, but themes were timeless with their story about personal growth, social structures, and, of course, love. But what made Clueless so beloved is that it centred a character who was, above all, an optimist.

For its lovable hero, Cher Horowitz, things will work out. Why wouldn’t they? Just as she tells her ex-stepbrother Josh, who expresses scepticism that she could get her teachers to change the grades on her report card, that she had “done it every other semester”.

Perhaps that’s the secret to Clueless’ enduring power. Earlier this year, its writer and director Amy Heckerling told the British podcast, Script Apart: “When you’re not so happy about the way things are going in the world, you could escape to this place of sunshine and fantasy and somewhat lovable characters, for the most part.”

Clueless changed the game, it supercharged teen movies which had been quiet after their 1980s peak, heralding the next decade of youth stories, and embedding the film’s snappy, specific lexicon into the wider culture – “As if!”, “Whatever!”, “Way harsh”, “buggin’” and “I was surfing the crimson wave”.

It even created its own sub-genre of teen literary adaptations, which included 10 Things I Hate About You/Taming of the Shrew, Easy A/The Scarlet Letter, Cruel Intentions/Les Liaisons Dangereuses, She’s All That/Pygmalion, She’s the Man/Twelfth Night and O/Othello.

Mona May’s costumes – Cher had 63 outfit changes – had every girl and woman aged between 10 and 49 rushing out to buy plaid skirts and argyle prints. If you couldn’t procure a fluff-topped pen, you made your own with supplies from Lincraft.

It didn’t matter if you couldn’t afford “totally important designer” Azzedine Alaia, you could still be part of the Clueless phenomenon.

But it almost didn’t happen at all.

Heckerling’s second film was the 1982 teen riot Fast Times at Ridgemont High, which featured among its all-star cast of young up-and-comers Sean Penn, Nicolas Cage and Jennifer Jason Leigh. It was the early Reagan era, and Fast Times was loose – it had sex, drinking, an abortion storyline and nudity.

It was also a commercial success, but 40 years ago, there were even fewer opportunities for women directors than there are now, and Heckerling didn’t get the leg-up in her career that should’ve been forthcoming.

She had to write the Look Who’s Talking movies so she could direct something, and by the early 1990s, was scouring for her next project.

At the time, Fox was looking for a teen TV series, and Clueless started life as a show called No Worries. Heckerling wrote the pilot, which had all the main characters that would eventually end up in Clueless, and Fox passed.

Heckerling changed agents, and her new rep, Ken Stovitz, took one look and said, “This is a movie”. But still no one was biting. The feedback was that there weren’t enough boys in the script, and you’re not going to get male audiences to come and see a movie about girls.

Every studio passed. That is, until Scott Rudin, a powerful producer who has since been put in the doghouse over many, many allegations over decades of abusive and bullying behaviour, read the script and liked it. Once Rudin was attached, it became hot property.

Alicia Silverstone was 17 years old during the casting process and had only one notable film to her name, The Crush, but she was known as the girl in the Aerosmith videos.

Heckerling loved her, but the studio insisted she see more actors, which included Tiffani-Amber Thiessen, Keri Russell, Reese Witherspoon, Gwyneth Paltrow, and even Angelina Jolie – the latter was deemed “too knowing” to play the innocent Cher, according to an oral history published by Vanity Fair.

Heckerling recalled that casting the role of Josh was the hardest. Ben Affleck read for it at one point, and so did Zach Braff.

When Paul Rudd came in, he had also read for Christian and Elton, and he eventually booked Josh, after he screen-tested well with Silverstone.

Brittany Murphy was a shoo-in for Tai from the start. Heckerling remembered her as “so bouncy and giggly and just so young, when you saw her, you just smiled”.

In fact, even the actors who didn’t get Clueless reads like a who’s-who – Seth Green and Jeremy Renner for Travis, Terence Howard and Dave Chappelle for Murray, and Lauryn Hill for Dionne. Sarah Michelle Gellar was offered the role of Amber, but the soap she was on at the time, All My Children, wouldn’t release her for the two weeks of filming. Similarly, Jerry Orbach couldn’t get off Law & Order to play Cher’s dad, Mel.

In a moment of life imitating art, during filming in Los Angeles, Rudd was mugged at gunpoint in a car park, just like Cher, and the Clueless script was in the backpack he surrendered to the assailant.

He told GQ in 2009: “I just remember the sounds of it, I remember people in the parking lot being really freaked out. But I just got very calm. Then I had to go to work the next day. It was a scene at a club. I was dancing, and I had just been shot at the night before.”

One of the film’s most iconic line readings – when Cher mispronounces Haitians as Hai-ti-ians – was an accident. Silverstone genuinely didn’t know how to say it, and Heckerling loved it so much, she kept it.

That scene was recreated last year for a Rakuten Super Bowl ad with Silverstone and a version of that famous yellow plaid skirt suit.

Clueless came to define mid-1990s teen culture, and given its enormous success — a $US56 million ($AUD85m) box office from a $US12m budget — everyone wanted a piece of it.

Every studio cried out for teen film scripts, and the next five years saw a saturation, culminating in the avalanche of 1999 during which at least a dozen major films in the genre were released, including Never Been Kissed, 10 Things I Hate About You and Jawbreaker.

In a full circle moment, the year after Clueless’s release, ABC commissioned a TV spin-off, but without Silverstone, Rudd, Murphy or Meyer, who didn’t return. The roles of Cher and Josh were recast with Rachel Blanchard and David Lascher, but Stacey Dash, Donald Faison, Elisa Donovan, Twink Caplan and Wallace Shawn reprised their characters.

It lasted three seasons, but that still wasn’t the end for Clueless. Heckerling adapted her film for a stage musical in 2018, initially as a jukebox musical, but reopened earlier this year with original songs.

And there’s a TV sequel in the works with Silverstone on board.

Even though Clueless was a tectonic film that recharted the course of teen movies and culture, the one person who didn’t do as well out of it as she should have was Heckerling.

“If you’re George Lucas and you create Star Wars, and then suddenly science fiction is acceptable after not being for so long, you’re golden,” Heckerling told Script Apart. “But I was just like, ‘What am I going to do next?’.”

Not that much, it turned out. Heckerling wrote and directed teen movie Loser, starring American Pie’s Jason Biggs and Mena Suvari in 2000, reunited with Rudd for largely forgotten 2007 rom-com I Could Never Be Your Woman and with Silverstone for little-seen 2012 horror comedy Vamps.

But she’ll always have Clueless. We’ll always have Clueless. Thirty years on and still as sharp, bright and winning as ever.

Clueless is streaming on Netflix, Disney and Paramount+