Clueless returns to theaters this weekend to mark its 30th anniversary. Just typing that out makes me feel like the Cryptkeeper. Has it really been a quarter-century since we first visited the halls of Bronson Alcott High School? In the years since, much has changed about teenage life, but Clueless – like Jane Austen’s 1815 novel, Emma, on which it’s based – remains smart, funny, relatable, and endlessly quotable.

Cher (Alicia Silverstone) is a very pretty and very rich teenager attending high school in Beverly Hills. She’s a bit selfish and naive, but has a good heart and only wants to help those around her. Cher’s favorite pastimes are makeovers and playing matchmaker, and with the help of her best friend Dee (Stacy Dash), they transform newcomer Tai (Brittany Murphy) into the school’s latest “it” girl. But in doing so, Cher actually learns some hard truths about herself, forcing her to examine who she is and what she wants.

Clueless Is The Perfect Adaptation

Amy Heckerling Masterfully Updates Jane Austen’s 19th Century Rom-Com For 1990s Beverly Hills

As adaptations go, it’s tough to find a better one than Clueless. Written and directed by Amy Heckerling, she keeps all the wit and charm of Austen’s novel and infuses it with more modern sensibilities. She takes Emma’s comedy of manners and seamlessly blends it with coming-of-age teen comedies, flawlessly transplanting characters and story beats. And her script is just dripping with some of the most unforgettable lines that, while clearly not pulled from the source material, still evoke the clever repartee of Austen’s heroines.

But Clueless’ success as an adaptation isn’t simply due to Cher being a pitch-perfect update of Emma, or because matchmaking is as much a part of high school social life as it was in Regency-era England. No, Clueless works so well as an adaptation because Heckerling respects the point of view of her young woman protagonist just as much as Austen did.

While there are certainly laughs to be pulled from Cher’s obsession with fashion or naivety about the world outside her high school, the movie doesn’t belittle her for it. Cher can act foolish, but she isn’t a fool. Her struggles might seem trivial to some, but they aren’t to her, and the film gives real consideration to her thoughts and feelings. It was rare to center young women when Austen was writing in the 1800s, and it still was in 1995 (and still today, sadly), but in doing so, Heckerling stays completely true to the spirit of Austen’s work.

Alicia Silverstone Gives A Career-Defining Performance

The Rest Of The Cast Is Stacked & Equally Iconic

Cher is among Alicia Silverstone’s first roles and it remains her very best. Cher is a character who could have been so unlikable, but Heckerling balances her selfish and airheaded behavior with an inner goodness that makes her easy to root for. But even then, the character wouldn’t have worked without Silverstone playing her with a bubbly energy and a knowing smirk, a small acknowledgment that she’s in on the joke and enjoying it just as much as you are.

What’s even better, though, is how Silverstone plays the moments of real emotion. The hurt when Tai is rude to her or the joy when she learns Josh (Paul Rudd) feels the same – it all feels so authentic. Without a doubt, Cher remains Silverstone’s best and most iconic role. It can be difficult for an actor to always live in the shadow of such a performance, but Cher is a character who will no doubt stand the test of time thanks to Silverstone.

Alongside her is a wildly impressive cast that only gets better with each watch: Paul Rudd, Brittany Murphy, Stacy Dash, Donald Faison, Breckin Meyer, Wallace Shawn! The whole ensemble is simply spectacular, without a single role miscast. Clueless’ many, many iconic lines would just not have become the quotable quotes they are without these performances.

On my most recent rewatch, I was particularly struck by how great Dan Hedaya is as Cher’s father, Mel. The character could have been really condescending, but true to the novel, Cher and her father share a very sweet relationship. This doesn’t stop Mel from being a bad-tempered character, it’s just rarely directed at Cher, and even then it’s always with a father’s love. “I got a .45 and a shovel, I doubt anyone would miss you,” is among the movie’s best lines, and I lose it every time I hear Hedaya deliver it.

Clueless Is An Early ’90s Time Capsule

But It Wasn’t Just The Fashion, Pagers, Or Cᴀssette Tapes That Really Had Me Nostalgic

A big reason why Clueless is such a blast to rewatch today is our nostalgia for the 1990s. Whether you lived through that decade or are only familiar with it through movies like this, it’s a trip to see the clothes, listen to the slang, and hear the music. It has an authentic ’90s vibe, too, given it’s of the time rather than a period piece made years later. But on my rewatch, what surprised me most was the funny ways Clueless had me feeling nostalgic.

On the way to the party in the valley, Dee and Murray are arguing over how Dee is reading the map. A paper map. It nearly took my breath away. But there was no GPS and no Google Maps, so what else could they do? That was a moment that really took me back, but another is when Cher orders a Starbucks coffee at Travis’ skate tournament. It was just a small, H๏τ coffee, not iced or a venti mocha frappe whatever. Just a cup of coffee. Can you even imagine getting something so simple from Starbucks today?

As someone who is now closer in age to Miss Geist than Cher (a realization I am reeling from), it’s still a lot of fun to revisit Clueless. Not just because it’s a throwback to the ’90s, but for the same reason any adult enjoys a teen comedy – it’s a trip back in time. Clueless is a deftly handled adaptation, an excellent coming-of-age tale, and a reminder of those days we spent “rolling with my homies”.

Clueless returns to theaters June 29-30.