Clueless Is a Great Teen Movie. It’s Also a Satire About the White and Wealthy.

We go back to this movie over and over because it’s fun. But we don’t talk enough about how it cleverly critiques Cher’s obliviousness. Photo: Paramount

Every week for the foreseeable future, Vulture will be selecting one film to watch as part of our Friday Night Movie Club. This week’s selection comes from TV critic Jen Chaney, who will begin her screening of Clueless on July 10 at 7 p.m. ET. Head to Vulture’s Twitter to catch her live commentary, and look ahead at next week’s movie here.

Jane Austen is widely considered an author of romantic comedies. But she was also a satirist who highlighted societal and economic inequities in a tone so wickedly wry that it could render most would-be boasters mute. In her novel Emma, she did both of these things: Spun a swoony story with multiple love triangles while also calling out her protagonist for her sheltered and blinkered view of the world.

When writer-director Amy Heckerling adapted Emma, taking Austen’s material and giving it a makeover that resulted in the sunny, sharp, and stylish Clueless, she did her own version of the same thing. She created a fun, escapist rom-com that, 25 years after its release on July 19, 1995, remains one of the most beloved teen movies of all time. But she also crafted a clever piece of satire. While the movie continues to generate conversation — about its ’90s aesthetic, its impeccable high-meets-low fashion, how it serves as exhibit A in the ongoing investigation into why Paul Rudd doesn’t age — it is less commonly discussed in this context.

For those who have always admired Clueless for its surface pleasures without considering what lies beneath them, this particular moment may seem like a strange time to revisit it. After all, we are currently living through what Hank Stuever at the Washington Post characterized as the summer of Karen, a season that has produced video after video of entitled white women losing their shit over such calamities as having to wear a mask at Trader Joe’s or put their damn dog on a leash. There are some who probably think of Clueless as a Karen movie, the story of a privileged Beverly Hills teenager who would probably have grown up to be the sort of privileged suburban woman in 2020 demanding that salons reopen so she can finally get her roots done. I will admit that if you approached a white woman of a certain age mid-tantrum over some perceived injustice and said, “Hey, have you seen the movie Clueless?� there is a strong chance she would pause, mid-meltdown, and go, “Oh my God, I love that movie!�

Clueless has always existed in a tricky space. There was and still is a giddy feeling that one derives from looking at all its eye-popping, girlish luxuries, the endless fashion ensembles, the nice cars, the pens with fuzzy poofs on the ends. As played by Alicia Silverstone with ebullience and charm exuding from her pores, Cher can seem aspirational.

Heckerling has fun with all those shiny trappings, but she also, just as Austen did, uses irony to show us what it looks like when a self-involved person with every advantage realizes she needs to stop thinking she’s right about everything and entitled to tell other people how to live. Yes, Clueless is a love story and a coming-of-age story. But above all other things, it’s a story about trying to be a better person, and specifically about a privileged young white woman trying to be a better person.

When we first meet Cher she is … not exactly trying to do that. In the opening sequence, she insists she lives a “way normal life for a teenage girl� but she says this while using a computer to pick out her school clothes, which are housed in a closet large enough to serve as a residence for four. From the very first moments of Clueless, it is obvious that Cher’s view of the word is completely at odds with what the world actually is. Much of the humor in the movie springs from that disconnect.

When Cher stands up to deliver a speech in Mr. Hall’s class, she is supremely confident in her understanding of world affairs even though she pronounces Haitians, “Hate-ee-uns.� While learning to drive, she questions why she should learn to park since “everywhere you go, there’s valet.� In one of her most heinous offenses, she tells her housekeeper, Lucy, that she “doesn’t speak Mexican.� Josh (Rudd), her stepbrother (kind of?), has to remind her that Lucy’s from El Salvador and that it’s extremely disrespectful to say what Cher just said.

Cher thinks she knows what’s best for everyone and tends to treat other people as projects instead of human beings with their own agency. She plays secret matchmaker for Mr. Hall (Wallace Shawn) and Ms. Geist (Twink Caplan). She performs a makeover on Tai (Brittany Murphy, RIP), even though she absolutely hasn’t asked for one. She tries to turn Christian (Justin Walker) into her boyfriend by force of will, until she realizes he’s gay and wouldn’t be interested. All of these are modernized echoes of events and relationships in Emma.

It’s easy to watch these scenes and conclude that the movie is laughing at Cher for being a dumb blonde and a busybody, but that’s an overly simplistic read. First of all, she’s not an idiot and she’s not completely devoid of compassion. In one scene, she proves that she remembers Hamlet better than a self-righteous college student does, albeit because Cher watched the Mel Gibson version. Because her single father is constantly working, she basically runs the household. When she realizes Christian wasn’t up-front about his sexual orientation, she doesn’t act like a brat about it. She accepts him for who he is and remains friends with him. (Clueless is not an aggressively progressive movie, but it did take some steps in the right direction for its time by focusing on teens that are gay as well as straight and Black as well as white, something that was astonishingly rare at the time.)

What’s both problematic and amusing about Cher is her ingrained belief that whatever she thinks, says, or does is correct, which is the very definition of white privilege. She has never really been challenged. She can sideswipe a car and the odds that she’ll ever face any real consequences for it are pretty much zero, because she’s well-off and has a litigious lawyer for a father.

The difference maker for her is Josh, who offers a perspective that’s contrary to what Cher’s inner monologue (which acts as the movie’s narration) has traditionally told her. At every turn, he calls her out on her rich white girl nonsense and lack of curiosity about what’s going on beyond the boundaries of Beverly Hills. Her growing respect and love for him is what ultimately makes her take a harder look at herself in the mirror, and not just to make sure her lip gloss has been properly applied.

The big altruistic acts that signify a change in Cher are, again, ironically comical in scale. She apologizes to Tai for meddling in her life and encourages her to go for Travis (Breckin Meyer), a member of the stoner clique that Cher admits she misjudged. She also takes the initiative to help with the Pismo Beach Disaster Relief Fund, which is a sly joke: Her big altruistic act is to help a bunch of Californians a few miles away by giving them stuff she no longer needs. It’s even slyer when you realize that the Pismo Beach disaster isn’t even a real thing.

By the end of the movie, there’s no reason to believe that Cher has been altered so significantly that she’s going to stop shopping at the mall and start donating all her white collarless shirts from Fred Segal to charity. But she has taken some positive steps. And even a positive step in a teen comedy can leave an important impression on its audience, especially those who saw it at a young age.

With its blasts of California sunshine and Supergrass, Clueless took a tale first told in 1815 and made it relevant to 1995. Because Heckerling was so good at critiquing the lack of perspective that often goes hand in hand with being white and wealthy, it’s still relevant now. But it’s also so enduringly watchable because it honors its protagonist’s humanity even when it’s castigating her for how out of touch she is. Heckerling really likes Cher, as she told me when I was writing my book about Clueless, As If, five years ago. She talked about her at times as if she were her own child, which, in a way, is how the movie treats her, too. In its satirical moments, Clueless shakes its head at Cher’s obliviousness. But it also forces her to quit complaining and start figuring out how to hold herself to a higher standard.

Clueless is available to stream with a subscription to Netflix and available to rent on Amazon Prime, YouTube, iTunes, Vudu, and Google Play.