It’s the film that launched a thousand “as if!”s, transformed Alicia Silverstone from Aerosmith video girl to bonafide movie star, and made us fall in love with Paul Rudd (for the first time of many). Clueless, a loose reimagining of Jane Austen’s Emma, was released in 1995 and immediately inspired millions of teenage girls to start wearing tanks over tees. If you haven’t watched Clueless since you last sported a plaid mini with platform heels, here’s a refresher. Cher Horowitz, a wealthy Beverly Hills teen, plays matchmaker and makeover artist to her teachers and friends, learns some valuable lessons, and in the end, finds love for herself as well.

So what say you, B? Did this rewatch of Clueless make you cringe?

B: I’ve actually watched Clueless thrice in 2018, and you know what? It feels like a shining beacon of sweet rom-coms and teen films from days gone by. It has some problematic blips, to be sure, but the real gross characters here (ELTON) are roundly shamed because our girl Jane Austen may have been all about marrying people off, but she was also all about happy endings.

Cher may be the girl who calls Spartacus “Sporatacus” and who credits Shakespeare quotes to Cliff’s Notes, but she’s also the kind-hearted girl who meets Tai and decides to give her a makeover and a solid start at a new school, and who donates expensive caviar to disaster relief, cause who says you can’t enjoy the nicer things in a crisis. Even her attorney father is basically a nice guy who turns out to be an A+ dad when she needs a pep talk about a crush. Likewise, Dionne, Christian, Tai, Murray and Josh are all sweet kids who weather the slings and arrows of teen life with the kind of grace that deserves a cheer or at least a hearty “pip pip!”

But, S, if our efforts so far have taught us anything, it’s that it simply can’t be all roses and woke, popular, straight boys who happily bro down with a “disco dancing, Oscar Wilde reading, Streisand ticket holding, friend of Dorothy.” Can it?

S: The thing about Clueless is that I can’t decide whether or not it’s problematic. In general, I agree with you. This movie is f-ing delightful, and although much of the central plot of this film revolves around the main characters chasing boys, Clueless does, unlike many teen films of its time, pass the Bechdel test. Sure, like you said, there are some problematic moments (among them a creepy “oh wow, you’re filling out there” from Josh, and my very favorite question: “Is it that time of the month again?” from Murray). But it’s also a film written by a woman about female friendships and female perspectives on finding love. Frankly, I loved every moment of my rewatch.

But I did leave the couch with a nagging feeling, and that’s what I want to explore.

Is Clueless too focused on image? And does it propagate an unhealthy message to teen girls that looks matter? I can’t decide if the Tai makeover is a “be your best self” situation or a “you need to bare your midriff if you want to be liked” message. The film also has a few body image blunders in my opinion, including Cher’s declaration that “I feel like a heifer” and Tai’s immediate conclusion jump that “it’s my hips, isn’t it” when Elton rebuffs her.

Like Cher and the gang, I was also in high school in the mid-90s and I remember the pressure to conform to a particular way of looking. At the time, I had also decided to stop shaving my legs in protest of societal expectations of females, and  made the conscious decision not to wear makeup. Even so, I eventually relented on the razor boycott, and was image-obsessed enough that I was devastated when my parents wouldn’t buy me Birkenstocks and Doc Martens (the “cool” footwear du jour). I also remember having conversations with my friends that closely mirrored the image-oriented chats had by Cher’s girl group.

So maybe Clueless was just cluing in on the teenage zeitgeist. Or maybe it was propagating a conversation that to this day, continues to damage teenage girls. I can’t decide.

B, we’ve explored the way the females in Clueless interact. How do the males stack up?


B: The boys of Bronson Alcott high and the adjacent males who aren’t Cher’s classmates are a curious bunch. Happily, they defy generalization to such a degree that I feel we must examine them one-by-one.

  • Elton – This perfect on paper snob is the guy Cher imagines as the perfect match for her new bestie Tai, but he turns out to be a rape-y jerk who couldn’t deign to imagine himself with Tai. And who sends mixed messages like putting Tai’s picture in his locker because Cher took it. And then there’s the awful shirt he wears to the party where he dances with Amber (who may or may not be wearing Cher’s dress). And we’re supposed to ship this guy with anyone? As if! There’s only one thing to say about this guy: he gives Cranberries fans a bad name.
  • Josh – Okay, Josh is both Cher’s (very short term) stepbrother and a college guy who ends up in love with a high school girl, but he’s also relentlessly charming and pure of heart. Smart and up to verbal sparring with Cher, he’s the guy who dances with a friend so she won’t feel left out and who inspires Cher to direct her spirit into positive actions. He’s also the guy you call to rescue you in the valley after you’ve been sexually harassed and robbed, so we’ll forgive him for the failings of his youth.
  • Christian – It’s a real bummer that Christian is so caught up in his own good times that he leaves Cher and Tai perched on a speaker at the party. But, otherwise, he’s a gentleman and a scholar. It could be argued that he leads Cher on to a degree, but I think it’s more a case that he hurts her without realizing he does. What with Murray and the crew immediately understanding that Christian is gay, he probably expects that Cher will pick up on his cues as well, but when he realizes what’s actually going on, he’s incredibly kind to her. Our favorite advice podcaster Anna Faris would probably agree that Christian goes out of his way to protect Cher’s heart along with his own. He also deserves a lot of props for rescuing Tai from the mall dudes who don’t understand flirting.

  • Murray – Sure, Murray and Dionne have a rather tempestuous relationship, but I think these kids are going to make it. When it comes to the harrowing incident on the highway, Murray steps up to keep his love and his friend safe, and that speaks volumes about the man he is already on his way to becoming. He shaves his head on a whim and deals some cutting remarks when in an argument, but ultimately, he’s a gem of a high school boyfriend.
  • Travis – Dear, sweet, Travis. When we first meet him, he’s not making great choices. But he is always, always a sweetheart to Tai, the object of his affection. And when she rather cruelly dismisses him as a slacker, he pays attention. The guy up and joins the 12-step program and goes back to Tai to present the new and improved version of himself. He doesn’t make any sweeping declarations or grand gestures, he lets his actions speak for him, and that makes him possibly the most stand-up guy in Clueless.
  • Mr. Hall – We don’t really see much of Mr. Hall and Miss Geist’s courtship other than a montage and their wedding, but good on this guy for trolling his students with awards for lateness and indulging their musings, no matter how off topic.

Okay, S, I think I’ve pretty much exhausted the top-tier roster of fellas in this picture. While I was unpacking all of those narratives, I came up with a question I’d love to hear your thoughts on. If we assume that Clueless revived the teen movie genre, ultimately setting the stage for the adolescent girl targeted pictures that flooded the late 90s and early 2000s, what does Amy Heckerling get right that so many of those other pictures missed? I have a theory of my own, but tell me yours first.

S: That’s easy. Clueless is one of the few films of its era that is told entirely from a female point of view. Look at other popular 90s teen flicks, and you’ll find an abundance of stories — at least in part — from the male perspective, presenting females as something to be pursued. For example:

  • Can’t Hardly Wait
  • She’s All That
  • American Pie
  • Varsity Blues
  • Cruel Intentions
  • Rushmore
  • Dazed and Confused

Of course, this is also the era that brought us such female-centric indie gems as But I’m a Cheerleader, Welcome to the Dollhouse and Slums of Beverly Hills, but Clueless stood out as one of the few major studio films to storytell from a teenage girl’s point of view.

B, hit me with your theory on this and then let’s get into some stray observations.

B: Point of view wasn’t the first differentiator that jumped out at me, but I couldn’t agree more that it is one of the things that gives Clueless that je ne sais quois that separates it from the pack. My theory hit me when I was browsing through, As If!, a delightful oral history of Clueless, so it’s less a theory and more a realization that Amy Heckerling and her team were even more brilliant than I gave them credit for. There’s quite a large section of the narrative dedicated to how the movie came to life and how this particular cast was assembled. And the names that were considered and dismissed are pretty astonishing. But the key point is that at the time of this picture, Alicia Silverstone was more or less only known for the Aerosmith videos and she was still young in spirit. Twink Caplan (producer/Ms. Geist) and Heckerling recalled meeting Alicia for lunch and marveling at how sweet and truly youthful she was. One of them explained that Alicia was still the girl who leaned over toward her glass to reach her straw instead of moving the entire drink toward her. It’s an observation I never would have made, but when I read that line I understood how they knew from very early on that Alicia was their Cher. Everyone else in the picture was similarly fresh, Brittany Murphy was still young enough that her mom had to join her on set per the SAG rules. Point being, Clueless is a high school movie that actually lets its stars be kids, and it found kids to play them. This isn’t Luke Perry in 90210, it’s a girl who doesn’t know how to pronounce “Haitians” mispronouncing “Haitians” on camera because Heckerling knew authenticity mattered.

TL;DR, Clueless didn’t try to make the kids at its center into adults, it took the time to find the real voice of kids at the moment.

  • Looking back, it’s possible I have to attribute my affection for plaid, Radiohead and shopping as stress relief to this picture.
  • I’m completely obsessed with this behind the scenes snap.
  • Amy Heckerling was behind the camera for Clueless, Fast Times, Loser, National Lampoon’s European Vacation and two Look Who’s Talking pictures, she also wrote about half of those pictures — why isn’t Hollywood knocking down her door for more original work?
  • I wish we could see what Brittany Murphy would be doing with her career today. I like to think she would be leading a prestigious mini-series on a premium cable network.
  • Why isn’t modern slang as clever as Clueless slang?

Okay S, give us the 411 on your stray observations and then let’s do some math.

S: It’s time to get more stray than a Val party with some observations!

  • I desperately want Cher’s touchscreen outfit planner.
  • Even with the 90s fashion and technology, this movie holds up…sans one word. That “R” bomb hit me like a ton of bricks.
  • Fun fact about the song that’s playing on the radio when Josh picks up Cher after she’s dumped by Elton in a parking lot. It’s a Counting Crows cover of “The Ghost in You” by The Psychedelic Furs, which was recorded live at Denver’s local adult alternative radio station (KBCO for you Denverites), and appeared on volumes 6 and 7 of the annual live recordings CD the radio station releases (Studio C for the Coloradans). I had volume 7. I was obsessed with this song – both because I loved the original and because I was enamored of Counting Crows (I had to buy two copies of their album August and Everything After because I played the first copy literally to its demise). Cut to nearly 15 years later, and I was in my car when this song came on the radio. I won tickets to a concert because I was the first caller to correctly identify the song’s original artist. Thanks, Clueless!

Now it’s time to get into our most capable looking outfits and do some math!

  • +2 cringes for the second film in a row to feature menstruation-based gaslighting.
  • -1 cringe because Murray was immediately shamed by the girls surrounding him.
  • +1 cringe each (2 total) for each time a girl blamed her own looks for a guy’s disinterest.
  • -2 cringes because this is an incredibly sex-positive movie. Dionne does not befall a tragedy because she loses her v-card, and Cher takes pride in her own virginity. The movie judges neither of them for their choices about their own sexuality.

That leaves me at one cringe. Because I’m still unsure as to whether the film’s image-focused dialogue is commentary on the teenage girl condition or a contributor to it, I think that’s fair. And at one cringe, I feel zero guilt continuing to love this film to pieces.

What do you think, B? Was I way harsh?

B: I think you’re pretty dead-on. While some of the films we’ve revisited have been total Monets, Clueless looks as good close-up as it does in the rose-tinted distance of nostalgia. There are a scant few moments where dated language jumps out to trip us up, but as we’ve discussed at length betwixt ourselves, this movie is the effervescent, bubbly, gem that only comes along once in a great while. In the hierarchy of teen films, Clueless sits very, very near the top, if not at the pinnacle.

I have only a couple of items to add to our equation:

  • +3 cringes for Elton, his snobbish tendencies and his aims to force Cher into vehicular sex in the parking lot of a liquor store in Sun Valley
  • -1 cringe each (3 total) for our diverse and dynamic leading ladies Cher, Dionne and Tai

Which leaves us at a single cringe for Clueless, a picture that’s come as close as any we’ve yet encountered to a perfect score — plaid skirts and donated caviar for everyone!


Don’t get too attached to this happy, shiny feeling, next time we’re revisiting another 90s film that’s very, very likely to raise our eyebrows: American Psycho.


Main image credit: Touchstone Pictures

About Shannon Fern

Anglophile. Star Wars apologist/prequel denier. Creator of small humans. Thrower of nearby objects upon hearing of pay inequity in popular media.