Lord knows what the gaggle of tenth graders chewing French fries and puffing Marlboro Lights made of the small septuagenarian woman who approached them at Jackson Hole, a burger joint on Ninety-first and Madison, claiming to be a magazine writer. Surely they knew nothing about Lillian Ross, the legend, who had written famous portraits of Ernest Hemingway and John Huston. (Who were they, anyway? Like, old guys?) Ross was fifty years into her career at The New Yorker, where she’d helped perfect the form of the Talk of the Town piece, with its cool, friendly eye and its limber, syncopated rhythms. For whatever reason, the Jackson Hole girls let her in on their chatter, as they planned their weekend and commiserated over a pop quiz in French class. “I was immediately fond of them, in their honesty and in their straightforwardness,” Ross later wrote. “I was deeply touched by the way they accepted me, strangely enough, as one of them.”

The resulting story, “The Shit-Kickers of Madison Avenue,” appeared in the magazine’s seventieth-anniversary issue, in February, 1995. It runs sixteen hundred words—long for a Talk piece, short for an instant classic—and is filled with gabby, anxious, kooky, self-dramatizing teen talk. (“I sweat Henry? Who you sweat? Anybody?”) Ross, a longtime Upper East Sider, had noticed the daily flight path of private-school kids—Nightingale girls, Buckley boys—along the west side of Madison (the “cool” side). She observed them in the wild, like a nature documentarian watching a herd of grazing antelopes, as they kissed hello and showed off their new lace-up boots, or “shit-kickers.” She begins, “The tenth graders heading up Madison Avenue at 7:30 A.M. to the private high schools are freshly liberated from their dental braces, and their teeth look pearly and magnificent. They are fifteen years old.” When I started writing Talk pieces, eleven years later, I read and reread “Shit-Kickers,” trying to absorb its joyful simplicity. Ross always made it look easy.

After her son started school, she heard from a teacher that Jackson Hole was an “in” hangout, so she infiltrates a table of girls there at lunch. Hot with anticipation for a party at a midtown club, the girls fuss over what they’ll wear and where they’ll pregame with vodka and orange juice. (One of them is grounded.) Ross catches them again on the other side of the weekend, disappointed; the party was a bust. Ross didn’t believe in tape recorders—she thought they got in the way of true listening—but her rendering of the girls’ dialogue invites the reader into their buzzing inner world. You can sense her delight in the upspeak, the exuberance, the rituals of fries and ketchup and onion rings. Like her friend J. D. Salinger, Ross loved the openness of young people and wrote about them often. She doesn’t name the girls in “Shit-Kickers,” identifying them as “the entrepreneur” or “the one who got home at three.” Nevertheless, as she recalled in her book “Reporting Back,” the piece “caused a bit of an uproar among some parents and teachers, but very few of them said that it was misrepresentative.”

It’s hard to see how anyone could be scandalized. “Shit-Kickers” has none of the salaciousness of Larry Clark’s film “Kids,” which came out that summer, or later depictions of Upper East Side preppies, such as “Cruel Intentions” and “Gossip Girl.” There’s no finger-wagging at their hedonism or their privilege; they’re just kids, still outgrowing their baby fat, but with the ersatz sophistication of New York City teens. I should know. I grew up on the Upper East Side, attended one of the schools mentioned in the piece, and sometimes went to Jackson Hole for burgers. I was in ninth grade when Ross’s subjects were in tenth. I saw how the oddity of adolescence in the upscale Manhattan of the Giuliani years—the too-lavish bar mitzvahs, shoplifting at Bloomingdale’s—crossed with normal teen-age preoccupations, like crushes and algebra tests. Jackson Hole is on Sixty-fourth now, and teen-agers still pass through there, speaking a different slang. But much else has changed. Six months after “Shit-Kickers” was published, Windows 95 hit retail, and kids started planning their weekends on e-mail, then AOL Instant Messenger, then Facebook, then Snapchat. Ross, in her winsome slice of New York life, had inadvertently captured the last gasp of teendom before it went online forever. ♦