‘Clueless’ just turned 25. Has it aged a day? As if!

The #UltimateSummerMovie Showdown is under way, and voters have chosen “Clueless” (1995) as their winner for Week 12, dedicated to movies first released in theaters from July 17-23 (between 1975 and 2019). Times film critic Justin Chang and TV reporter Yvonne Villarreal look back at the legacy of Amy Heckerling’s romantic-comedy classic, its Jane Austen roots and its contributions to the look and language of an entire generation of teenagers.

JUSTIN CHANG: Yvonne, I’m delighted to have you join me for this latest of our Ultimate Summer Movie Showdown conversations — about as delighted, really, as I was to see “Clueless” come out on top this week. The outcome was a bit of a surprise, and it took some doing. With the exception of a few earlier champs like “Bridesmaids,” this is a series whose fan base so far tends to favor action and horror. The closest runner-up this week was James Cameron’s “Aliens,” which of course has legions of fans.

But then, so does “Clueless,” which turned 25 earlier this month and has long since cemented its reputation as an American classic. It may appall you to hear that although I vividly remember seeing it in theaters 25 years ago, in the summer of ’95, I haven’t gone back to it since — until just this past week, when I gladly sat down to rewatch it on Netflix. One of the many reasons I’m glad you’re here to discuss it with me, Yvonne, is your expertise: Based on what you’ve told me, you probably saw this movie more times in a given teenage week than I have in my whole life.

Still, even with a 25-year gap, I was struck by how utterly familiar so many individual beats and moments were. Partly that’s because, as with so many generation-defining hits, “Clueless” is a movie whose cheeky one-liners (“Ugh, as if!”), stars-in-the-making (Paul Rudd!) and brightly hued costumes (where to begin …) have taken on a pop-cultural life of their own. It’s also partly due to Alicia Silverstone’s still-wonderful performance as Cher, the Beverly Hills-born Emma Woodhouse so perfectly and endearingly described by the title.

One big difference? When I first saw this movie, I was only 12 and had no idea that Amy Heckerling had set out to make a goofy 20th century riff on a Jane Austen classic. Twenty-five years later, having read “Emma” and watched several of its more straightforward adaptations, it’s a pleasure to see not only just how well “Clueless” holds up, but how faithfully and intelligently it reproduces the jewel-like construction of Austen’s novel — a story about how wrong we can be in matters of the heart, whether they’re everyone else’s or our own.

YVONNE VILLARREAL: Justin, thanks for having me! If it makes you feel any better, I saw the movie just a few weeks after turning 10 and, without a doubt, was oblivious to its “Emma” influence (surely delighting Gwyneth Paltrow) and the extent of its wonderfully witty and sharp charm. I promise the shortsightedness was rectified with age and countless viewings. Still, while I couldn’t tell you one thing I remember about my birthday party that year, I can easily recall the excitement I felt in the movie theater from hearing the opening notes of “the Muffs’ cover of “Kids in America” (a group and song I had never heard) thumping as the white stars in Paramount’s title card flew into their iconic semicircle position before a montage kicked in of Cher and her friends doing cool-kid things. It was like I was about to hang out with the popular older sister I didn’t have but desperately wanted.

While I wasn’t the target demographic then, I totally consider it my teen movie. I was drawn to the excess and the stylish wardrobe (even Cher’s motorized closet!). But the wonder and awe over all that only worked because of Cher’s ebullient personality. For all her shallowness and privilege and meddling tendencies, she is someone who desires to be better — even while sideswiping a car. The clever way Heckerling critiques the lack of perspective is something I only came to fully admire later.

And, of course, if we’re talking about the enduring appeal of “Clueless,” we must acknowledge the ridiculously quotable dialogue. You know what I’m talking about: referring to someone as “a full-on Monet” or sprinkling “sporadically” into a sentence or saying you’re “surfing the crimson wave” when a girl is on her period. My childish brain didn’t grasp a lot of it then, but it wanted to. It’s that playful and wicked use of language that keeps the film feeling timeless (even with all the pagers and Cher’s dad insisting everywhere in L.A. only takes 20 minutes of drive time). I think it’s why I was determined to memorize the dialogue as a kid. I couldn’t replicate Cher’s wealth or privilege, but I could talk like her and her friends!

CHANG: Wow, Yvonne, that was way existential. Also, do you like Billie Holiday? (I love him.) But seriously, you’re spot-on about how ridiculously quotable “Clueless” is, and in particular how brilliant Heckerling is at using language, at devising a wittily stylized teen vernacular for her characters. As you note, some of the props and drive-by references in “Clueless” may sound a little dated now (“I can’t find my Cranberries CD!” “Is this like a Noxzema commercial or what?”), but the actual way the characters speak, the contours and cadences of the language itself, still feels irresistibly fresh and sharp and buoyant. The reason I think it holds up so well is that Heckerling wasn’t attempting some tired approximation of how kids spoke, the way a lot of forgettable youth comedies might have; she let her characters speak brilliantly for themselves.

In “Clueless,” language is never just a means of getting from point A to point B; it’s an expression of personal style — and few things, of course, matter more to Cher than style. Her verbal strategies are at once dizzyingly circuitous and weirdly intuitive. When she says, “It does not say RSVP on the Statue of Liberty” (and how great and sad is it that a 25-year-old teen comedy has a more humane understanding of immigration policy than some of our elected officials), your first instinct might be to laugh and roll your eyes — but the closer you listen, the more everything she says makes its own pretzel-logic sense. The point being that while Cher may be clueless in some respects, she’s remarkably perceptive, sensitive and savvy in others. (Just like Emma!)

There’s one dialogue exchange in particular that lingers in the memory, and it happens when Cher has an argument with Tai (Brittany Murphy), the eager-to-please newcomer that she and Dionne (Stacey Dash) have adopted as their new best friend/makeover project. It may be just a silly teen spat, but there’s something about the way Cher says “That was way harsh, Tai” that still cuts to the core. Maybe it’s the wounded look in Silverstone’s eyes, or the equal hurt in Murphy’s expression. Or maybe it’s because there’s something unshakably poignant about every scene with Murphy now, in light of her tragic death in 2009, when she was just 32. It’s the kind of real-world tragedy that might make a lesser teen comedy seem trite or trivial by comparison. But for me it actually has the opposite effect of making the bubble-gum fairy-tale world of “Clueless” feel all the more precious, all the more inviting to return to — a world that, even at 25, never gets old.

VILLARREAL: Ah, yes, the “You’re a virgin who can’t drive” scene — one of the great teenager spats with the shadiest insult in cinematic history, IMO. (Makes you wonder what modern burn would be way harsh now? “You’re a TikTok user who hasn’t gone viral”???) But seriously, the way Murphy’s Tai purses her lips with attitude as she shoots the verbal bullet remains exquisite to this day. And it all speaks to Heckerling’s depiction of rich and complicated female friendships that, at the core, ring true to the teenage experience — you get jealous sometimes, you say mean things sometimes, but you wouldn’t dare give up rollin’ with the homies (sorry, had to) for anything.

Early on, we get a sense of the closeness between Cher and Dionne through their love of shopping and the way they scheme together and help each other — and, like, they’re both named after great singers of the past who now do infomercials. When ensembly-challenged Tai is introduced, yes, Cher and Dionne consider her another project to take on — making her over from frumpy teen to total Betty. But while it’s superficial, it’s not mean. They genuinely want to help Tai. And, in the process, the three grow closer, supporting and encouraging each other — however misguided that support and encouragement may be at times.

And while there is a romance between Cher and her sort-of-stepbrother Josh (Paul Rudd), who is kind of a Baldwin, slowly bubbling to the surface, that relationship doesn’t take precedence over her friendships. It’s that spat with Tai that leads Cher to her water-fountain-igniting realization that she is totally butt crazy in love with Josh. But even while Cher is processing those feelings, there is still resolution for the two friends. They exchange a heartfelt apology — at a skateboarding event, no less — and promise to never fight again. For me, the way “Clueless” showed romantic love didn’t have to take the place of friendships has always been something I was grateful to see at a young age.