David Letterman Getty Images Entertainment/Dimitrios Kambouris
By Chris Vespoli

AWKWARD NEW YORK is a weekly column about the uncomfortable experiences of Chris Vespoli in and around NYC. Every Tuesday is another cringe-worthy account, from being fat shamed by a Dunkin’ Donuts employee to crashing Fashion Week.

David Letterman steps down as host of the Late Show tomorrow night, ending a 22-year run on CBS, and capping a media career that has spanned five decades. But long before he set up shop in the Ed Sullivan Theater, before he was infamously passed over for The Tonight Show in favor of his fellow Comedy Store alum Jay Leno, before he trail blazed Late Night on NBC, and even before he hosted a morning show on the same network, Dave was already breaking ground far away from New York City, in his hometown of Indianapolis, Indiana.

In what’s become the stuff of legend, Letterman, while working as a weatherman at a local television station, congratulated a tropical storm on being upgraded to a hurricane, live on the air. That one quip would serve as both blueprint and microcosm for Letterman’s brand of off-kilter comedy: subversive, sarcasm-spiked irreverence that goes against the grain of tradition, social norms, and sometimes, good taste.

It was the beginning of awkwardness as a television commodity — a commodity Letterman would develop, and perfect, here in New York.

I was born in 1984, two years after Letterman’s Late Night debuted on NBC in the 12:30 slot following The Tonight Show Starring Johnny Carson, where Letterman had cut his (gapped) teeth as a guest host. Though I have no real memories of Late Night during that time, I still have a deep appreciation and understanding of how truly groundbreaking it was, in much the same way I do The Beatles or the moon landing. (Yes, I just sort of compared Letterman’s tenure on Late Night to two of the most culturally significant milestones of the 20th century. That’s because there’s no overstating Letterman’s impact on television. Plus, let’s be honest — the moon landing was probably faked.)

Much like imagining what pop music was like before The Beatles, so too is it difficult to imagine what late-night comedy was like in the era before Letterman, if one hadn’t lived through it. When Letterman took the reins at Late Night, the talk show format was already 30 years old and cemented into a tried-and-true foundation of monologues, guest banter, and character bits. Extending the path he forged on his short-lived morning program, Letterman eschewed ancient talk show tropes (and dress shoes; he wore sneakers with his suits), often denying his viewers the comfort they’d come to expect in a late-night show, while his feet enjoyed plenty.

Some of the show’s more memorable awkward moments included:

A staged incident in which pro-wrestler Jerry Lawler very believably assaulted comedian and fellow guest Andy Kaufman, eliciting gasps from the audience and a stream of bleeped expletives from a browbeaten Kaufman.

A tense interview with Cher, during which she called Dave an asshole to his face.

An entire episode in which the screen slowly rotated throughout the hour — turning the picture upside down and then all the way around again.

Dadaist remote camera pieces that saw Dave interrupting the Today show with a bullhorn, throwing stuff off roofs of buildings, and surprising his new corporate bosses at General Electric with a fruit basket, which building security met with a cold, cringe-worthy reception.

And let’s not forget the Top Ten List, Stupid Pet Tricks, Bud Melman, the Velcro suit, and dozens of other classic segments that have become synonymous with Letterman.

Whereas Carson’s Tonight Show was providing chuckles to middle-agers while softly lulling them to sleep, Letterman was shotgunning spaced-out fever dreams down the throats of bleary-eyed college kids to the brink of 1:30 in the morning.

After NBC gave The Tonight Show to Leno, Letterman shifted to the 11:30 slot on CBS without missing a beat in 1993. On the Late Show, Dave upped the ante with his taped pieces. He messed with customers while working a shift in a McDonald’s drive-thru, and in another, filmed in LA, ordered 1,200 tacos from a Taco Bell and handed them out to strangers from the back of a convertible. And things inside the studio got weirder, too, with nonsensical, gamified bits like “Will It Float?” “Know Your Cuts of Meat,” “Psychic Sandwich,” and “Is This Anything?” It wasn’t clear what was funnier: when the absurd premises would hit with the audience, or Dave and bandleader Paul Shaffer’s indignant commitment to them when they didn’t. It was during this time in the ’90s when I fell in love with Dave, and also his worthy successor back over at Late Night, Conan O’Brien.

As the Late Show moved into the mid-2000s, Letterman’s interviews achieved peak uneasiness. His dry, cutting, “who the fuck are you?” attitude crashed through the flimsy facades of Internet-age celebs, channeling his own audience’s disdain for them — from mercilessly grilling Paris Hilton on her time in jail, to his masterful takedown of an aloof, bearded, dark-shaded, seemingly drugged-out Joaquin Phoenix, remarking at the end of the interview, “Joaquin, I’m sorry you couldn’t be here tonight.”

But the best part about Letterman has been his willingness to turn the awkwardness in on himself. The night he admitted to engaging in sexual affairs with women who worked at the show, and acknowledged the resulting extortion plot of which he became a target, Dave bore his shame to the world and reaffirmed himself as perhaps the most vulnerable, flawed, and therefore relatable television personality ever. Not since Jack Paar quit on the air had a talk show host exposed so much of his humanity in front of the camera.

And even amidst that awkwardness, Dave was able to glean humor. It’s what he does. It’s what he’s always done. And I feel lucky to have been able to watch him do it, even if what I saw was just a fraction of his legendary career.

There’s nothing awkward about saying this: Thank you, Dave. I’ll miss you.

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