It was the summer of Bad Boys and Batman Forever when we first locked eyes on Cher Horowitz and her gang, and Clueless became the iconic film of a generation. 

That makes Cher’s exploits – and the first time I remember setting eyes on Paul Rudd – 25 years old. Like, as if!

Often called “the ultimate teen movie” – something writer/director Amy Heckerling knew a lot about, given her work on Fast Times at Ridgemont High – and a “pop culture masterpiece”, Clueless was Heckerling’s take on 90s teen culture, inspired by Jane Austen’s Emma and Gentlemen Prefer Blondes. 

And it was/still is glorious. With one of the best soundtracks ever made and a host of young talent that went on to bigger things (Alicia Silverstone, Paul Rudd, Brittany Murphy, Breckin Myer), Clueless is just a joyous bounce around Beverley Hills before the Real Housewives took over.

“This is Heckerling’s movie, through and through,” writes Allie Gemmill for Collider. “It’s the result of great timing, a distinct voice, a collection of generation-defining actors, music cues so perfect it hurts, and outfits so good it hurts even more — all of it was possible because it began with Heckerling.”

The studios didn’t get it – way harsh

Clueless originally struggled to find a home, with many dismissing it as a teen romp, all gloss and no meaning. Seemingly every studio passed on Heckerling’s masterpiece, often citing they ‘didn’t get the humour’. Like the labels that passed on the Beatles, they lived to regret the decision; the humour is one of the defining and enduring elements of Clueless. 

And endure it does. Endlessly.

“Clueless […] starts a more ironic, knowing trend that lovingly pokes fun at both its characters and the genre conventions itself – much like Austen did,” write Phoebe Macrossan and Jessica Ford for The Conversation. 

“This irony and knowingness are perhaps what makes Clueless so enduring. There is a depth to the writing that allows the viewer to laugh both with and at the characters. This can be attributed to Heckerling’s respect for them and their problems. As Paul Rudd said: ‘One of the things that I think is very clear in her work […] is just how much she loves young people and doesn’t talk down to them.’”

“Clueless continues to resonate because there’s so much happening beneath its trim, 97-minute surface for anyone to admire,” writes Keaton Bell for Vogue. “It’s a glossy teen comedy, biting high school satire, deeply satisfying rom-com, and subversive literary adaptation all at once.”

Silverstone told Vogue: “I’m always amazed at the longevity of Clueless. It’s incredible that so many people love this film and not only continue to love it but continue to rediscover it… So many moms who were my age when it came out are so excited to show it to their sons and daughters now. I don’t know how to explain why or what made Clueless what it was, but I know it happened and I know that people continue to love it. And it never gets old, so that’s the good news. People always say Oh you must be so sick of it. But what’s there to be sick of? People liking the movie you’re in? It truly doesn’t get better.”

Clueless’s grip on pop culture has only tightened in the last 25 years; think of Iggy Azalea’s Fancy video, or the still-prominent calls of “As if!”. It may have stood on the shoulders of John Hughes, but there are also many movies from the last quarter-century that follow firmly in the footsteps of Clueless: where would Legally Blonde, Mean Girls, Easy A or even Booksmart be without Heckling’s trailblazing?

“Searching for a boy in high school is as useless as searching for meaning in a Pauly Shore movie.”

Clueless was my introduction to the concept of the Valley Girl, and my conversation was soon peppered with Cher-isms. “As if”, of course, became part of my vernacular. I never quite brought myself to refer to Baldwins, Monets, nor admit I was totally buggin. And I definitely had a total, 100% crush on Cher’s ex-step-brother Josh – what a dreamboat.

It was also the first time I “worked” a film premiere. I’d seen it two or three times before it was even released, thanks to my role as a reporter on a newspaper written for high school students by high school students. We ran a competition to win tickets to a special screening, and it was so exciting. It made me realise I could actually write professionally about what I loved most: pop culture.

So yes, Clueless means a lot to me. I’ve lost count of the amount of times I’ve watched the thing. I can quote it. My CD copy of the soundtrack got scratched to buggery because I played it so much – incidentally, also my entry into “cool” music after being a proper teenage girl loving pretty boy bands.

To think of this celluloid icon as being 25 does make me feel a little old, but never wistful for my teen years: Clueless was the making of me, setting me on the trajectory to where I am now. And for that, I shall be forever grateful.

Reminisce with me and listen to the Clueless soundtrack now on Spotify.