David Letterman raised me: Growing up with the Late Show host.

David Letterman Raised Me

David Letterman Raised Me

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May 10 2015 9:00 PM

David Letterman Raised Me

His subversive comedy transformed the entertainment landscape—and made me who I am today.

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Letterman was an unlikely hero for an ’80s kid, but a hero nonetheless.

Photo illustration by Slate. Photo of girl by Pressmaster/Shutterstock. Still of David Letterman by Jamie Squire/Allsport.

Strange kids seem stranger for cultivating solitary enthusiasms. And strangeness may be a factor of birth order: If you’re the youngest in your family by a lot—if, say, all your siblings are in or out of college by the time you’re reading chapter books—you may try to narrow the distance between you and them by liking the stuff you think they like: their thick grown-up novels, their enigmatic college-radio bands, their cultish late-night shows.

Jessica Winter Jessica Winter

Jessica Winter is Slate’s features editor and the author of the novel Break in Case of Emergency.

Liking the stuff you think they like does little to make you feel less alone in your house, but it does succeed in widening the distance between you and your actual peers, who like different stuff. In short, you lack adaptive skills. You are not good at figuring out how to be a kid. But you do figure out how to program the silver Quasar VCR your household acquires in 1985 when you are 8 years old, and for the next several years, you will wake up an hour early each morning to watch Late Night With David Letterman before school. And for a short while in the early ’90s, when A&E starts showing reruns of Late Night from before your time, you will spend two hours with Letterman every day—one of those hours with a young and relatively mellow Letterman, a Letterman who was not yet encumbered by mannerisms and who occasionally wore sweater vests.

To my suburban elementary-school self, David Letterman was a window into urban adult life. He was a figure both accessible and aspirational, crackling with frictions of personality: a Midwestern loner-type yet somehow the hippest guy in New York City; a guy beset by self-doubt and self-loathing yet confident enough to build a late-night institution around himself; a guy palpably uncomfortable around people who made a stratospheric living by talking to people; a guy with a pathological aversion to embarrassment who pursued embarrassment of himself and others as a vocation—maybe as a way of cauterizing a primal wound.

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As a gawky and badly socialized child, I, too, had a fear of embarrassment. But fear of something is its own form of fascination, which may be why I was so fascinated by Late Night’s many sublime embarrassments. The infamous (and, it turned out, staged) brawl between Andy Kaufman and wrestler Jerry Lawler—in which shit-talking turned to bitch-slapping turned to screaming and coffee-tossing—was ugly-funny, bizarrely intimate, and humiliating for everyone involved, like if two of your cousins got into a bar fight and for some reason your homeroom teacher was tending the bar. There was the night when the Band’s Levon Helm didn’t show up for his guest spot, and so Letterman interviewed the staffer who booked him instead, a little duet of matter-of-fact mortification. There was, of course, Late Night mascot Larry “Bud” Melman, a phenomenon whose genius lay in the ambiguity about just how far in or out on the joke he was. This joke reached its apotheosis in Larry’s triumphant journey to the Port Authority Bus Terminal, where he attempted to operate a microphone and handed out hot towels.

Even as a kid, I understood intuitively that all of this seemed somehow unsuited for broadcast, that Late Night’s static of awkwardness and banality was exactly the stuff that got edited out of most television programs. This was a show that carved an entire segment out of the fact that producer Barbara Gaines shared a name and a few interests with another person named Barbara Gaines. Marcel Duchamp hung a toilet in a gallery and called it art; David Letterman came up with a list of Top 10 Words That Almost Rhyme with “Peas” and called it—well, actually, he never would have called it comedy, even if others did. (What I’d forgotten until I watched that Top 10 clip is that the lists, which lampooned magazine polls and listicles, began as a form of media criticism, just as the parodic aspects of Late Night scanned as television criticism.) Along with these surreal bits and failed gags and excruciating silences was an unspoken camaraderie with me, the viewer, the lonely weirdo at home who for some unearthly reason was watching this mess. Late Night didn’t seem made to be watched—not quite—which of course made it riveting to watch.

The most enchanting aspect of Late Night, at least to a kid like me, was that it seemed so private. This was true even before Letterman began indulging his own tics and perseverations and verbal fixations as if no one were looking (and sometimes as if the whole world were looking, which it was on Oscar Night 1995, aka the night of “Oprah, Uma”). Late Night was unsolicitous of the viewer, just as Letterman was often unsolicitous of his guests. (But never unsolicitous of his dog guests. No man has ever loved dogs like David Letterman loves dogs.) The cramped and shabby set, where grizzled stagehands and rumpled young producers milled around uneasily at the margins, appeared to be a space created specifically for strange people cultivating solitary enthusiasms. (A 1985 Rolling Stone cover story on Letterman itemized a few of these guests: “a guy who keeps weird congealed old food in his dresser drawer … Another guest keeps snowballs from different years … a woman named Alba Ballard dresses parrots to look like Cyndi Lauper and Dee Snider from Twisted Sister.”) A sloppy spotlight trained shakily on Letterman’s guests as they strode out from the dingy wings, as if for a 3 a.m. set at a fourth-tier comedy club where they’d try out material on people who weren’t really listening and who would never remember what they heard.

I knew what that felt like because I tried to get my peers to share my interest in Letterman for years. I cringe to think of the Ralph Wiggum–like surety with which I attempted to start Letterman-related conversations with a fellow third-grader whose surname happened to be Lettman—an effort that was positively Letterman-esque in its hapless embrace of inane semi-coincidence. I had trouble accepting that my peers were into Alf and Garbage Pail Kids and that blurting out “They pelted us with rocks and garbage!” at the cafeteria table would not be an irresistibly mysterious invitation to my secret Late Night world. These people watched cartoons in the morning. The man in their lives was Kirk Cameron or maybe Jordan from New Kids on the Block. Meanwhile I was gleaning what I could about human sexuality from the wacko frisson between Letterman and Sandra Bernhard, which turned each of her appearances into a kind of televised foreplay, especially on the night that Madonna showed up. When, decades later, I conducted an informal poll of Letterman Babies around my age for reactions to his sextortion scandal, not only did I search in vain for anyone whose perception of him shifted a millimeter; I also searched in vain for anyone from my generation who was even surprised. This, I believe, is due to Sandra Bernhard. (Also Julia Roberts. And also Drew Barrymore. Oh, and Madeleine Smithberg.)

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I started to let Letterman slip away from me at the exact moment of his mainstream pinnacle: When he moved to CBS in 1993, the watered-down 11:35 incarnation of the show proved to be too loud, too bright, too public. (Letterman, in retrospect, seems to agree, recently telling the New York Times’ Dave Itzkoff, “We came out of the chute, going a million miles an hour. And … we just sort of said, ‘Really, can we go a million miles an hour again?’ And we tried, and we couldn’t.”) Late Night’s not-ready-for-prime-time-or-really-anytime intimacy was lost in a bigger theater. The guest list went celebrities-only, and the celebrities, sadly, always showed up. It’s now been over 20 years since I stopped scrambling out of bed in the mornings to watch VHS tapes of his show. And yet I feel bereft whenever I envision the cultural landscape without Letterman, whose last-ever Late Show airs on May 20.

Not that there’s any way ever to erase him from that landscape. Letterman’s influence on the entertainment world is so totalizing as to be invisible—it doesn’t bear explicitly Letterman-like markers so much as it simply ingested his entire sensibility. If you think something is funny, chances are that Letterman is right there, in on the joke with you. His public-access production values and halting parade of misfits anticipated Tim and Eric. His constant low-level hum of discomfort anticipated the advent of cringe comedy. His insider-y tweaking of network brass anticipated the Sheinhardt Wig Company of 30 Rock. His endless waterfall of instant-classic remote segments anticipated Kimmel and Fallon’s reorganization of late-night programming as discrete segments built to go viral. His overall attitude of reflexive irony and cheerful pessimism anticipated the invention of Generation X. “I think if you have any sense,” Letterman once said, “you’ll adopt the view of life that if the bucket of shit can explode, it will explode.”

People who grew up loving Letterman didn’t idolize him, exactly; someone whose personal gestalt involves an exploding bucket of shit naturally resists idolatry. He didn’t become a father figure for me or a first celebrity crush. But in part because of his evident gift for the aphorism and partly by dint of his being a tall man in a suit in my house all the time, Letterman over the years acquired a moral stature. This seemed to be borne out by his genteel comportment over two botched Tonight Show handovers, by his evident decency (he effectively bankrolled the final years of comedian George Miller’s life, and handed an entire Late Show over to Warren Zevon when he was dying), and by his fierce loyalty (repeatedly having Mary Tyler Moore and Jimmie Walker on as non sequitur Late Night guests, apparently because they both gave Letterman jobs when he was a struggling young comic). And then there was his growing willingness to be seen as a vulnerable human being, whether in his return to The Late Show after quintuple bypass surgery in 2000 or a year and a half later in his cold open following the 9/11 attacks, when he spoke simply and memorably to the nation’s collective grief. The edgy, irritable, discomfiting wiseass could comfort America when it mattered.

But he was always comforting to me. He kept me company. He sent me off to school every morning with an absurd little private joke in my head, like a note tucked away in my lunch box. And into my 20s and 30s, when my daily Letterman viewings had long lapsed, he was still milling around in the background, muttering pleasantly to himself, cackling at ephemera. On a few occasions this past winter, pinned to a couch by a newborn around the clock in an hourless blur, I’d find myself flipping him on at 11:35 partly to orient myself in time, but partly just to know he was around—this odd and lonely-seeming person pacing my silent house, laughing gently both at and with my strange solitary enthusiasms, him and me in on the joke together.