30 Years Ago, Clueless Gave Us An Icon Of Self-Assurance In Cher

Did you know that Clueless turns 30 this year? As if! But seriously, it does — and if that fact makes this millennial writer feel ancient, well, I'm not bugging over it. When I recently rewatched the classic comedy for the first time in at least a decade, it was clear why it remains legendary. As one of my Gen Z co-workers so kindly reminded me, "You were alive when Clueless came out? Iconic!" And honestly, they're not wrong. With its mix of clever writing, timeless themes of love and friendship, and flawless '90s fashion, it changed pop culture forever.

I was 12 years old when Clueless opened in theaters, and having no idea what high school was actually like, I'll admit it pretty much set me up for disappointment. What do you mean I wouldn't get to wear designer clothes, drive a fancy car, and casually orchestrate my teachers' love lives? Total bummer. (Although I would eventually come to own a couple of plaid skirts and knee-high socks, which, I gotta say, made me feel like a Betty.)

For those who need a refresher, Clueless is loosely based on Jane Austen's Emma, and follows Cher Horowitz (Alicia Silverstone), a stylish, wealthy, and well-intentioned teen who rules her Beverly Hills high school with confidence and optimism, alongside her best friend, Dionne (Stacy Dash). Playing matchmaker for her teachers and giving the clueless new girl, Tai (Brittany Murphy), a makeover, Cher thinks she has life all figured out. But when Tai starts stealing her spotlight (and her crush), she realizes her perfect world might need a makeover of its own... especially when she figures out she's totally in love with her ex-step-brother Josh (Paul Rudd).

Of course, I could wax poetic about the movie's iconic clothing and clever dialogue — not to mention ask why, in 2025, we still don't have Cher's styling app. But we know all that already!

More than anything, what stood out to me now, even more so than as a kid, was that Clueless shows high schoolers as real people with their own problems, hopes, and desires without turning into some heavy-handed after-school special. The movie just lets them be, even as they wear their designer bucket hats and baby tees.

They have dating drama, like Dionne and Murray (Donald Faison). They struggle to fit in, like Tai. They have crushes who reject them, like Travis (Breckin Meyer). They stress over grades, like Cher negotiating her way from a C+ to an A-. On the surface, it all seems light and fluffy, but underneath, it's just real because teenage problems are real.

And what makes it even better? Every character has their own distinct personality. These aren't just stereotypical "mean girls" or "nerds" or "jocks": They are all fully formed and relatable. There's a casualness to their interactions. These kids know each other, and in turn, I know them. I went to high school with a Travis and Dionne. I knew an Amber (Elisa Donovan).

At the center of it all is, of course, Cher, someone who, while still figuring out what she wants in life, is already so confident in who she is. Even if people around her dismiss her as an airhead, she isn't one. There's always a reason behind what she does, and she believes in what she says. Check out her debate in that first scene. She literally believes that the people who showed up at her dad's 50th garden party without an RSVP are the same as Haitians immigrating to the USA. Even when her logic doesn't make sense to anyone else, she owns it.

Something else I never fully appreciated about Cher until now is how endearing her optimism and positivity are and how that reflects her determination. She genuinely believes in what she's doing, whether it's matching her teachers or helping Tai, and wants to help. Sure, her efforts seem a little misguided (like donating old ski equipment to an environmental charity drive isn't exactly groundbreaking), but she does it with the purest of intentions.

She panics at the thought of ruining her Alaia dress when forced to lie down on the ground at gunpoint, but that's the thing: Cher knows who she is, she knows what she likes, and she stands by her convictions, even if it means not damaging couture. What matters to her might seem superficial to others, but she is unapologetically herself.

Cher might have a moment of self-doubt — "Everything I think and everything I do is wrong," she says in a rare moment of insecurity — but the irony is, she's not clueless. She wasn't wrong for believing that Elton (Jeremy Sisto) wanted Tai, thinking Christian was her dream guy, or wanting Josh to like her for who she is. She just wants to believe in people, in love, in the best possible version of things.

As Alicia Silverstone once said, what makes Cher so ridiculous and lovable is how seriously she takes everything. She's so sincere in everything she does, and that's exactly what writer-director Amy Heckerling wanted to explore: a character who is extremely optimistic and free of self-doubt.

In the end, Cher isn't clueless at all. She never strays from who she is, and it's that kind of purity and self-assurance I aspire to. Who wouldn't want to have the confidence to call their own victory before it even happens? As she says to Josh before catching the bouquet at the wedding, "It's in the bag." Because when you know who you are, everything else just falls into place.

Just like the perfect outfit.