Clueless

Directed By: Amy Heckerling
Other Notable Films From Heckerling: Fast Times at Ridgemont High, Look Who’s Talking, A Night at the Roxbury
Starring: Alicia Silverstone, Paul Rudd, Brittany Murphy, Stacey Dash, Donald Faison
Screenplay By: Amy Heckerling
Movie Synopsis: A high school student in Beverly Hills navigates the pitfalls—and delights—of teenage life with panache.
Signature Line: “Ugh, as if.”

THE INTRODUCTION
An accounting of time, and people, and context

Clueless, 1995’s culture-shaping coming-of-age comedy about an affluent high school girl, opens with a montage: First, we see the movie’s protagonist—15-year-old Cher Horowitz, played to effervescent perfection by Alicia Silverstone—driving a beautiful open-air Jeep down a perfectly manicured Beverly Hills street with several of her stylish friends in tow. Then we see a smiling Cher walking down Rodeo Drive, the luxury shopping bags in her hands serving as proof of an afternoon well spent. Then a series of smash cuts show Cher and everyone in her orbit in the other settings they inhabit as socialites—Cher and her best friend chat at their posh, well-funded school; a collection of kids swim in someone’s extremely well-appointed private pool; a handful of girls lord over the food court of a high-end mall.

For the viewer, the message is immediately clear: You’re looking at a group of kids who live a life better than you do.

Here’s the thing, though: Whereas most movies about rich, popular high school students revolve around characters who weaponize cruelty and exclusivity to maintain their place in the hierarchy,1 Clueless, a loose adaptation of Emma, Jane Austen’s beloved 19th century comedy of manners, leans the other direction. As a movie, it’s considerate, and it’s warm, and it’s thoughtful. It invites you in—not to be a detached spectator, but to be a participant. And it’s able to be so convincing in its inclusivity because its central character—the abovementioned Cher Horowitz—is so convincing in hers.

We never see Cher chase popularity in the movie; we only ever see her pursue fulfillment. She wants to have a meaningful relationship with her father, and a meaningful relationship with her friends, and, most importantly, a meaningful relationship with herself. Her journey, bubbly and carefree as it may seem, is a surprisingly deep fount of life lessons.

As such, this week’s essay is structured a little differently.

Rather than the usual timestamped rewatch with notes, it’s a collection of all the lessons Clueless offers its audience—even those of us without an infinite credit line.

THE LESSONS
As relayed by Clueless

I know everyone who opened this essay did so hoping to find a conversation about Josh and Cher’s relationship somewhere in it, so let’s go ahead and have it right now: