His show included stars, but they were never the point—the charge came from the bits. Illustration by Stanley Chow

On May 7th, two weeks before the end of “Late Show with David Letterman,” on CBS, the host delivered one of his final lists, “Top Ten Surprising Facts About Sesame Street.” The entries, every one a harsh gem, riffed on a documentary about the actor who played Big Bird, but they also satirized the way that the media had recently been strip-mining Letterman’s decades on television, seeking revealing nuggets. No. 9: “The earliest Muppets were made from hollowed-out animal carcasses.” No. 2 got a huge, rolling, in-on-it laugh from the audience: “Oscar the Grouch slightly nicer since announcing May 20th retirement.” The No. 1 fact about “Sesame Street”? “There’s also a guy working the puppeteer.”

For more than thirty years, David Letterman has been the guy working the talk-show host. But he’s never hidden how tricky it is to move those levers, which has been his appeal to fans: in a job made for smoothies, he’s kept showing us his flaws, those spikes of anger and anxiety, almost despite himself. Now that Letterman’s a flinty codger, an establishment figure, it’s become difficult to recall just how revolutionary his style of meta-comedy once felt. But back when I was sixteen, trapped in the snoozy early eighties and desperate for something rude and wild, Letterman seemed like an anarchist. His manner suggested that TV could puncture the culture, rather than prop it up. My friends, particularly the guys, became his acolytes, quoting his catchphrases (“They pelted us with rocks and garbage”) and copying his deadpan affect. All of us imprinted like ducklings on his persona, the nice guy with the mean streak, making the world safe for smart comedy.

The truth is, the show that Letterman oversaw in those early years was a far lighter, freer, more strange and cerebral and surreal project than it eventually became. It began as the brainchild of Dave and his girlfriend at the time, the comedy writer Merrill Markoe, who was the show’s first head writer. She invented one-offs, like Dog Poetry, and perennial segments, like Stupid Pet Tricks. (They considered doing Stupid Baby Tricks, but worried about the legal implications.) The pair, who were together for a decade, met at the Comedy Store, in Los Angeles. Their aesthetics were different—Markoe was a Berkeley art-school graduate, while Letterman was an Indiana frat boy who had majored in television and radio—but they shared an ironic mind-set, a suspicion of show-biz sycophancy, and a desire to break formulas, during a period when the medium had hardened, and taken on a Vegas-y, old-Hollywood heaviness. In 1980, pulling from earlier experimentalists, like Ernie Kovacs and Steve Allen, they built a daytime talk show on NBC, full of oddball pranks, which bored housewives but won over college kids. When it flopped, the network was nevertheless eager to keep Dave on the schedule, so it bumped Tom Snyder and gave him Snyder’s slot, at 12:30 a.m.—this was before TiVo and Hulu, when you had to stay up late to catch the funky stuff. Within two years, he was a hero to wiseacres everywhere.

On the surface, the early Letterman resembled his mentor, the icy superstar Johnny Carson: he was apolitical, he was Midwestern, he had a repressive manner and lanky college-boy looks. (Don’t let the gap-toothed grin fool you. Squint, and Letterman is Harrison Ford.) But he vibrated with a contradictory charisma: he had a discomfort with back-patting and schmoozing, an odd characteristic for a man whose longtime dream job was TV host.

In a sense, Letterman was a bridge between two eras of male superstars. Like the white-guy comedians of the seventies, Bill Murray and Chevy Chase and Steve Martin, he was a smart-ass, a trickster. And yet, even in 1982, when “Late Night with David Letterman” premièred, he presaged something else, an obsession with what was authentic, the kind of preoccupation that would dominate the nineties, inflecting figures like David Foster Wallace and Kurt Cobain, famous men who were desperate for rock-star fame and then flamboyantly and publicly hated the stuff once they got it. Like Holden Caulfield, Letterman was on the defense against looking like (or being) a phony, looking like (or being) a sellout, and curdling into a Hollywood jerk. In 1984, in a Playboy interview, Letterman talked about what a drag it was to meet Andy Rooney and realize that his act wasn’t an act: Rooney “doesn’t just appear to be a nasty curmudgeon, he is a nasty curmudgeon.” Already, Letterman had a melancholy vision of what fame could turn you into, if you let your guard down: “I hate the notion that celebrities deserve to be treated with some kind of deference.”

The early “Late Night” included stars, but they were never the point. The charge came from the bits, the “remotes,” the pranks—a circus of eccentricity, from the monkey-cam to Chris Elliott climbing out from beneath the bleachers. Regulars included Larry (Bud) Melman, an elderly character actor who was both mocked and adored. One episode was filmed, for no reason, with a camera that rotated three hundred and sixty degrees. The goal was surprise, which often involved Letterman doing slapstick with a proto-“Jackass” bent. My primal memory of the show is of Dave, in a Velcro suit, getting tossed up onto a wall from a catapult—although, when I looked at a clip recently, I saw that my fond memories had exaggerated a mere mini-trampoline. The suit wasn’t the joke, though. The joke was Letterman, who isn’t zany but polite, asking the Velcro representative questions about this revolutionary substance. On the wall, immobilized, he quietly deadpans, “There’s very little I can do from this position.”

It was a prescient zinger. Once Letterman became truly famous, the captain of a giant machine that demanded ratings, it was harder to stay nimble. Over the decades—through the bruising “late-night wars” with Jay Leno, past a sex scandal (handled with refreshing bluntness) and a heart attack, and into his late-curmudgeon era on CBS—Letterman has occasionally seemed at risk of dissolving, Cheshire Cat style, into his grin, glasses, and cigar. His influence spread so wide that his innovations became clichés. Once the Internet arrived, he never mastered the viral clip. Pop culture often seemed to bore him. He stayed inside more. Fame made it harder to play games with strangers, the way that a niche cable host, like the latter-day Lettermans Billy Eichner and Eric Andre, might. But, even as his teen acolytes grew up to become his cable competition, Letterman retained an itchy, mercurial self-consciousness, and an inability to fake it with strangers—in a genre devoted to snake-oil synergy, he remained a lousy salesman.

Long before Letterman labelled himself Oscar the Grouch, Cher famously called him an “asshole,” sensing, not incorrectly, his bias against her kind of glitz. But when you watch the whole interview, which aired in 1986, Cher is the one who comes off like a jerk, jabbing the host before he’s done anything wrong. Then Letterman reacts beautifully. He shifts his jaw, he grins, he runs his hand over his forehead. He rattles his page of questions, saying, “No, we’ve got a lot of great stuff here”—rattle, rattle—“really good stuff here. A lot of really interesting, provocative kind of things.” He continues, “What do you mean, ‘Is this as good as it gets?’? Like, what would have been a better thing to say to you?” Cher doubles down: if Letterman doesn’t like a guest, it shows, she says. What flares up between them feels like chemistry, something amazing—and this was the quality he had with many of his more eccentric guests, from Andy Kaufman and Pee-wee Herman to the funny women whom he clearly appreciated, like Amy Sedaris. Even with Cher, Letterman doesn’t get ruder; instead, his voice softens, as he tries to bond over their age (both were around forty). Somewhere in there, he proves her wrong: there’s value, and there’s dynamism, in a host who can’t quite hide what he hates and what he loves.