An Ode To David Letterman, Accidental King Of Comedy

Some people learned to love the New York City they met in Audrey Hepburn's morning-after swan through deserted Midtown in Breakfast At Tiffany's. Or Woody Allen's black-and-white Manhattan, peopled with urbane neurotics and pulsing to a Gershwin tune. I learned to love the New York in David Letterman punch lines about Port Authority pervs, traffic light window-washers, and weirdos on the D train.

When David Letterman announced this week that he would be retiring from CBS' The Late Show at the end of 2015, I couldn't decide which it made me feel more: sad or old. Like Johnny Carson had been for him, Letterman was the first person I can remember idolizing, imitating, and being genuinely intrigued by. I adored his wit, his weirdness, the fact that he was equal parts tortured cynicism and goofy Midwestern guilelessness. He was also, it must be said, my first-ever crush, which began when I was five, and by 13 had developed into full-blown obsession, complete with plans to move to New York to intern for the show (and be discovered and become wildly successful and make boys who didn't like me back jealous, of course). I remember staying up at night in middle school, not just watching, but studying The Late Show, taping and watching them over and over again. When I ran out of VHS tapes, I'd transcribe my favorite jokes by hand onto a legal pad for later study, complete with pidgin accent marks attempting to replicate Dave's delivery. I remember one brief, throwaway line, when a guest told Letterman that Aaron Spelling had a bowling alley in his home. "Oh," he said, with a mischievous gleam in his eye, "Now there's a touch of class." A devastatingly economical line that I use to this day, whenever some tacky, rich-guy pretentiousness needs deflating. Even as a kid, I recognized that there was power in that type of wit, and I longed to wield it. It's more than a little sad to admit how many times I practiced delivering that line with Dave's perfect archness — my own Rupert Pupkin moment.

David Letterman landed his first gig on television as host of a daytime talk show, in June of 1980, three weeks before I was born. YouTube clips of that show are scant, but the few I've seen prove that it was truly too offbeat and edgy for daytime, for network TV, and almost certainly for audiences in 1980. In a time before irony took over the world, when the resolutely un-hip hokum of Dallas and Love Boat dominated the airwaves, audiences were, predictably, not ready to sip their morning coffee with a straight-looking, but oddly edgy host in mismatched suits who joked about getting drunk the night prior and shooting out street lights with a .357.

The morning show was cancelled in short order, freeing Letterman to develop Late Night With David Letterman, the show he hosted weeknights at 12:30 a.m. from 1982 through 1993 on NBC. From studio 6A in Rockefeller Center, Letterman played host one of the most inventive and anarchic shows ever aired on television. There, he gleefully lampooned the trite, pandering, showbizzy conventions of the old-guard talk show hosts — the Merv Griffins and Bryant Gumbels of the world — and in doing so, installed irony as the world's default humor mode.

Late Night dispensed with celebrity guests as a primary source of entertainment — partially due to a non-compete embargo imposed by Johnny Carson, Letterman's idol and host of the 11:30 lead-in show. Instead, Late Night assembled its own cadre of cranks, losers, and misfits that appeared in brilliant and bizarre interviews and location segments. Watch Chris Elliott insist he's not channeling Leno when he shows up for an interview in an oversized blazer and prosthetic chin. Or watch Letterman play against Larry "Bud" Melman, as he passes out hot towels to travelers at New York's notoriously grimy Port Authority bus terminal (wearing a red "welcome" sash, of course). This clip is an object lesson in modern comedy. Letterman never chases a joke. He hardly even makes any. He puts real people in a contrived setup and relishes the oddness that ensues. Watching Letterman swing from awkwardness to childlike delight at Melman's glassy-eyed grin and microphone-challenged interview skills is a thing of joy forever.

Letterman also installed one of the comedy world's first female head writers, the brilliant and acerbic Merrill Markoe, who conceived of some of the show's most famous bits, like "Stupid Pet Tricks," "Stupid Human Tricks," "Viewer Mail," and my personal favorite, the pointlessly destructive location segments. In one, Letterman throws things off a five story tower. We get to see a bowling ball, doll house, wedding cake, and balloon full of guacamole reach terminal velocity. In another, Dave visits a machine shop in New Jersey and uses their 50-ton hydraulic press to crush a canned ham, a stack of pancakes, and a Mr. Potato Head doll in a 50-ton hydraulic press to smithereens. Those segments blew my mind when I was a kid. They were the anarchic analog to Mr. Rogers' segments where crayons, graham crackers, and other things beloved of my childhood were made. On Letterman's show nothing was sacred, least of all glasses-wearing, potato-themed toys. I remember the way the studio audience howled with a slightly dangerous excitement when Mr. Potato Head's glasses flew off his face, and his head puffed, then exploded. Learning that grown-ups could be as pointlessly destructive as kids — and that they found these warped, nihilistic things funny — felt like I was seeing behind the curtain, into some secret part of adulthood that was a little dark, certainly more interesting, and usually well-hidden from me.

There were the straight jokes, too, the Top Ten lists that mythologized New York as a crime-ridden hellscape. This was a perspective that Letterman inherited from Carson, who made mugger and flasher jokes with the best of them. The difference being, of course, that Carson had left New York in the '60s, before society crumbled, and now goofed on the bankrupt metropolis in an expensive suit from a studio in Burbank. Letterman reported from live the belly of the beast, Ed Koch's New York, where crack ruled, crime was pocketbook-clutchingly frequent, and the murder rate was a terrifying five times what it is now. A quick survey of Top Ten Lists from 1987 to 1993 reveal punch lines about chalk outlines, trash piles, crummy baseball teams, stray bullets, subway flashers, and the sad, East River fates of mob informants. But, Dave's New York was the funhouse-mirror flipside of Travis Bickle's seamy pimp-and-peep-show New York. I remember laughing for days over Dave's number one "Bernhard Goetz pickup line: Which do you think is funnier — Deathwish II or Deathwish III?" What other show could make comedy out of such a mess? This was absurdity as antidote to urban malaise.

Sure, Dave sometimes veered into staleness. There were the endless Oprah jokes of the '80s, the two-year block of Monica Lewinsky monologues in the late '90s. But even then, Dave had a magical ability to master any situation, to come out on top of an awkward interview or hacky set-up. When a joke died, he could deploy cutting self-deprecation, or a manic, high-hitched laugh ("hee heee!") that perfectly conveyed his "this is what I'm working with, folks" humiliation and always won the audience back. Without ever being overly ingratiating like Leno, endearingly schticky like Conan, or projecting the commanding, urbane charm of Carson, Dave and his bemused regular-guy routine disguised the fact that he was the canniest, smartest guy in the room, and always got the audience on his side. I felt fairly certain I could never be as masterful as Dave at working a room, or being in front of a camera. But, when I found out that, backstage, there was a team of people who wrote for David Letterman, that's the exact moment I decided to be a writer.

I haven't kept up with Dave's show as much in — oh, the last 10 years. In the few clips I've seen, the magic is a little worn off, and I can't tell whether it's the show, or the fact that Dave's sensibility has so thoroughly permeated our culture, that it can't possibly feel as fresh as it used to (I call this The Simpsons Effect). I remember watching his famous response to the Leno-Conan debacle, and being taken aback by his vitriol (even given Leno's duplicity and their, uh, complicated past). It seemed like Dave's angst and antagonism, always visible as a corona around his best jokes, had hardened into straight-up spleen-venting. Carson would never have done that. Hell, the old Letterman would never have done that. He seemed ungracious and, worse, humorless. He seemed like a cranky old man.

But then, Letterman is old now. He turned 67 yesterday, and his stated reasons for retiring include spending more time with his family. I suspect that the retirement of his arch rival, Jay Leno, may have deflated Dave a bit, too. When Letterman hands the Late Show's reins to Stephen Colbert, he leaves behind a completely changed late-night landscape of 40-something hosts who grew up idolizing him, not Carson. He started out the jester in this corny, old-showbiz world, accidentally breathed new life into a flagging format by thoroughly (if lovingly) mocking it, and now, he's the king. That must be weird for a born shit-strirrer.

Letterman leaving TV is a real "end of an era" moment for me, but at the risk of sounding trite, he'll always be with me, mostly because I've been soaking in his sensibilities since I was born. I can count the people who made me who I am on one hand, and Dave is on there (so is George Meyer, which surely says something about me). Dave leaves with me a love of the deep weirdness of normal people. And, he indoctrinated me into the secret knowledge that makes depressives comedy's most ardent fans: That wit and absurdity can transform crappy circumstances into a kind of gleeful nihilism that's probably as close as we'll get to happiness.

I'll also always have an enduring obsession with Dave's type — have I mentioned I've had not one, but two long-term relationships with gap-toothed, whip-smart, sarcastic Aries males, one of whom shared Letterman's birthday, the other born the day before? My coworkers' noses wrinkled when I told them Dave was my first love. It doesn't make sense if you only know the intern-dating, cranky Dave of late, I guess. But, the old Dave showed me and a lot of other born outsiders a new world, where wit was the only weapon you needed against demoralization. Even on a Brooklyn-bound D train.