Speak the truth, Alicia Silverstone: “Searching for a boy in high school is as useless as looking for meaning in a Pauly Shore movie.” Happy 30th birthday to Clueless, Amy Heckerling’s coming-of-age comedy starring the dynamic duo of Silverstone and Stacey Dash. Ever since it arrived in July 1995, it’s been prized as a Nineties masterpiece, as anyone will agree unless they’re a virgin who can’t drive. Silverstone stars as teen fashion plate and Wildean wit Cher Horowitz, shopping her way through an L.A. full of Baldwins, Bettys, and Monets. The late great Brittany Murphy shines as the Mentos-loving skater girl. (You’re rolling with the homies in our hearts, Brit.) Did the Nineties have a more classic movie? As if!
Clueless still haunts our cultural imagination, lingering in our minds like a Cranberries CD left on the quad. It sums up everything cool about its era — the ultimate Nineties time capsule, whether you’re into pastels or flannel. I attended the 90s Con a couple of years ago, with a reunion of the cast, the whole place packed with fans dressed in Clueless fashion — so many Chers in yellow plaid, so many Dionnes in fancy hats. On the red carpet, I asked Stacey Dash why this movie is so timeless. She stared me dead in the eye and said, “Because Cher and Dionne were GENIUS.” She wasn’t lying.
Over a decade after directing the Eighties’ peak comedy, teen or otherwise — Fast Times at Ridgemont High, written by Cameron Crowe — Amy Heckerling did the same favor for the grunge decade by writing and directing Clueless. It’s relentlessly quotable, one long warp-speed barrage of one-liners in a totally invented teen-girl speak. In her classroom debate, Cher defends the immigrants of L.A. in a speech that’s timelier than ever these days. “If the government could just get to the kitchen, rearrange some things, we could certainly party with the Haitians,” she says. “In conclusion, may I please remind you that it does NOT say RSVP on the Statue of Liberty!”
Cher and Dionne have one of the coolest movie friendships ever, two Beverly Hills fashionistas named after “great singers of the past who now do infomercials.” (Nobody had any way of knowing the O.G. Cher still had her peak ahead of her, with her 1999 signature hit “Believe.”) What brought these two soulmates together? As Cher explains, “She’s my friend because we both know what it’s like to have people be jealous of us.”
But Clueless was so radical because of Heckerling’s generous affection for her characters — she made a movie about a pair of vain, flippant, narcissistic, fashion-obsessed girls, without judging them for being this way. Their loyalty and love for each other is rewarded just by being cooler and funnier than anyone else around. As in an Oscar Wilde comedy, it satirizes the tiniest, most absurd rituals, rules, and fetishes of social manners without moralizing, with wit as the only virtue that matters.
Seeing Clueless in the mall theater, with a crowd of fellow first-timers — that was one of the truly exquisite things about being alive in the summer of 1995, along with hearing “Waterfalls” on the radio, arguing over Wowee Zowee vs. Alien Lanes, and Kramer’s ASSMAN license plate. The laughter shifted from “group hysteria” to “communal asphyxiation” right at the moment Amber made the whateverrrr fingers. Some movies take time to find their audience, but not Clueless — practically everybody decided this was a classic, and we weren’t wrong about that.
People immediately started saying things like “she’s going postal” or “we’re Audi” or “I’m surfing the crimson wave.” (One of Heckerling’s genius moves was to reject the idea of authentic teen lingo; she made up practically everything.) The summer was full of iconic popcorn flicks, from Babe to Friday to Species, but Clueless was the most loc’d out. Every single character gets to be funny. Dan Hedaya sets the gold-medal standard for gruff dads in Nineties teen movies. (His only competition: Larry Miller as Julia Stiles’ dad in Ten Things I Hate About You.)
Elisa Donovan’s Amber deserved her own spin-off, Daria-style. In her showcase moment, she interrupts a gym class on the tennis court to say, “My plastic surgeon doesn’t want me doing any activity where balls are flying at my nose.” Dionne replies, “Well, there goes your social life.”
It’s based on Jane Austen’s 1815 novel Emma — it arrived the same year as the epochal BBC Pride and Prejudice with Jennifer Ehle and Colin Firth. It was an index of the decade’s Jane Austen obsession, to the point where Clueless was swiftly followed by two other Emma adaptations in 1996, Kate Beckinsale’s BBC version and Gwyneth Paltrow’s Hollywood version.
True, Clueless is slightly too faithful, since it keeps the novel’s dodgiest plot twist: the heroine falls in love with her ex-step-sibling, Paul Rudd’s Josh. Her dad was briefly married to his mom, years ago, but as Mel says, “You divorce wives, not children.” This was already a queasy subplot in 1815, and it didn’t exactly age well over the next 180 years — blame it on Jane. Clueless picks up this plot point for just a few lines, then wisely ignores it for the rest of the movie, but it still gives what Cher would call “an overwhelming sense of ickiness.”
Alicia’s debut was the 1993 camp-trash thriller The Crush, one of those “wait, that really happened?” movies; she stars as the murderous teen equestrienne trying to seduce her sweaty-looking adult neighbor Cary Elwes. But at least one customer enjoyed The Crush: Aerosmith’s video director Marty Callner, who cast her in the band’s classic MTV Alicia Trilogy of “Cryin’,” “Amazing,” and “Crazy.” “He liked what he saw in the movie,” Silverstone told Rolling Stone in her 1995 cover story. “And what he saw was a good actress, not a pretty girl.”
Damn straight. Alicia made a plucky (not sexualized) teen queen in the Aerosmith videos — shoplifting, flipping off exes, hijacking tractors, kickboxing bad guys, etc. One of the many fans totally buggin’ for these videos was Heckerling. “Here’s how I found Alicia,” she said. “I was minding my own business on my treadmill watching MTV when I saw ‘Cryin” and just went cuckoo bananas.”
The ballad of Cher and Dionne has remained a cultural obsession ever since. Clueless became a TV sitcom from 1996 to 1999, with Rachel Blanchard as Cher, with Stacey Dash and Alisa Donovan returning along with Heckerling. It’s an underrated yet worthy part of the Clueless canon, with more screen time for Donovan’s Amber (“Enjoy your riverfront property on De Nile!”) and gags like Dash saying, “In ten years we’ll be 27 — almost old enough to play high-school students on TV!”
Clueless turned into a Broadway musical in 2018, with a jukebox soundtrack of Nineties hits: “No Scrubs,” “Torn,” “You Get What You Give,” like that. As for Cher’s computerized closet organizer, it’s become a Gen Z meme in itself. There’s a glut of self-proclaimed “Clueless closet apps” like Indyx and Whering promising to create the most iconic wardrobe in cinema history.
I saw the Clueless cast reunion at the 90s Con in 2023, with Silverstone, Dash, Donovan, and Breckin Meyer. You could snag a private photo with Alicia for $75 or the whole gang for $225 — a bargain considering that the Beverly Hills 90210 cast was charging $280. (Jawbreaker was also a good deal at $170.) Most of the fan photos had everyone doing the “whatever” fingers. But it was therapeutic to sit in a room full of hardcore Clueless fans, the kind who’ve read Elisa Donovan’s grief memoir Wake Me Before You Leave, or maybe even Stacey Dash’s book about her conservative politics, which at least had the excellent title, There Goes My Social Life.
The reunion panel was so poignant, especially when everyone talked about how much they miss Brittany Murphy. The stars got asked which cassettes they wore out on the set. For Alicia, it was Alanis’ Jagged Little Pill; Stacey picked Nirvana, Elisa picked Public Enemy and Breckin picked Rage Against The Machine. But it was unexpectedly bittersweet when a fan asked their favorite lines from the movie; Alicia put on a Brittany voice to say, “You’re a virgin who can’t drive!” We all felt that.
The soundtrack alone was enough to make it a classic, with Radiohead (“Fake Plastic Trees”), Supergrass (“Alright”), Coolio, Counting Crows, the Beasties, Luscious Jackson, Smoking Popes, even a freaking Velocity Girl indie single. It’s a movie where the Mighty Mighty Bosstones are playing the school dance. Josh’s big flaw to Cher is that “he listens to complaint rock.” When she hears him cranking Radiohead, she asks, “What is it about college and cry-baby music?”
Clueless epitomizes the California-girl aesthetic that has mesmerized the world from Beach Blanket Bingo to the Go-Gos to Olivia Rodrigo, who once visited the Biden White House dressed in total Cher Horowitz drag, a key 2020s high-water mark in the Clueless legacy. (A pink Chanel suit from — of all years — 1995.) Yet Cher is a woman of principle who lives by her code: to thine own self be true, as Hamlet didn’t quite say. (It was that Polonius dude.)
Clueless has gone down in history for its over-the-top couture — the rare movie that makes a celebrity out of the fashion designer, Mona May. She’s celebrating the anniversary with a new book this fall, The Fashion of Clueless As babe-culture historian Abbey Bender has pointed out, May’s signature touch is marabou, “that fluffy, frivolous, unabashedly feminine trim,” but “in May’s hands, marabou is akin to a power suit.” It defines the movie’s hyper-femme aesthetic — Cher and Dionne’s absurdly ornate coordinated ensembles are a visual language they share, their friend code.
Yet Clueless also sums up everything tolerant and humane about its era. It was one of the first high-school flicks where the gay dude is also the cool dude, without ever getting played as a joke or a tragic figure. Travis, the skater boy who provides the stoner humor, later joins a 12-step program and starts providing sobriety humor, yet he’s funny both ways. (“This clarity thing has brought me to like, a whole new level with my skating!”) Dionne and Murray have a warmth that’s miles away from standard teen-movie romance. There’s even cross-generational empathy, like when Cher sets up two middle-aged teachers. When Miss Geist finds romance with Mr. Hall, the girls gush, “Old people can be so sweet!” At one point Travis muses, “Like, the way I feel about the Rolling Stones is the way my kids are going to feel about Nine Inch Nails. So I really shouldn’t torment my mom anymore, huh?” This was a Dalai Lama-level spiritual insight by Nineties standards.
This April brought the 411 that Clueless will get a reboot on Peacock, with Silverstone reprising her role as the now-adult Cher. Heckerling and Silverstone will produce; the writers are Jordan Weiss along with the teen-TV titans, Josh Schwartz and Stephanie Savage, who created Gossip Girl and The OC, two of the finest Clueless tributes. Too soon to know if anyone else from the cast will return—Stacey Dash? Paul Rudd? Dionne and Murray — still together, right? Did Cher patent her wardrobe software? Will Dan Hedaya return as her angrier-than-ever dad Mel? Wallace Shawn as Mr. Hall? Are he and Miss Geist raising Tai’s daughter together? All we know is that Clueless lives on because it represents the most utopian Nineties values — so all are welcome here. Now more than ever, it does not say RSVP on this Statue of Liberty.
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