Goodnight, David Letterman: A Celebration

Writers and artists reflect on 33 iconic years of the pencil-tapping comic.


    Artwork by Cap Blackard (Buy Prints + More)

    David Letterman is a once in lifetime entertainer whose worldwide pants straddled the classic days of late night television and the edgier wit of the modern era. He’s the missing link between the stylish Rat Pack bravado of Johnny Carson and the Dadaist outpouring of personalities like Conan O’Brien, Stephen Colbert, and even his own No. 1 fan Jimmy Kimmel. Not bad for a gap-toothed kid from Indianapolis who started as a TV weatherman.

    Today, he’s a 68-year-old veteran. Most of his contemporaries have been replaced, changed formats, or are still secretly plotting their next sinister return from a luxury car garage in Burbank. By comparison, Dave’s the sole survivor. He’s going out on top and on his own terms, which is rare in any field, let alone the entertainment industry. Celebrities, musicians, comedians, artists, politicians, and fans of all ages have made pilgrimages to the Ed Sullivan Theatre to spend one final evening with their late night hero.

    Tonight, it’s all over. Which is why we’re taking a closer look back at how it was even possible for one funny man to shape so much of our world. Ahead, you’ll find a comprehensive editorial spread out over three unique sections, which we’ve broken down into a simple menu for you to peruse below. Think of it as a breezy guide to a complicated icon, or treat it as an online celebration, culled together by a collection of writers who really, really, really wanted to talk about Dave.


    So, pop the champagne, find an old pencil, and start tapping away.

    I. The Humanity of David Letterman

    II. Top 10 Late Night/Show Performances

    III. 33 Years, 33 Essential Memories

    The Humanity of David Letterman

    by Ryan Bray

    david letterman1 Goodnight, David Letterman: A Celebration

    Norm MacDonald is on the verge of tears. Standing before the audience inside the Ed Sullivan Theater, the normally immoveable comic chokes on his words as he recalls his favorite David Letterman joke, one about a friendly family outing spent trailing a garbage truck. It’s a jarring image, especially for a guy best known by many for his merciless takedowns of O.J. Simpson and Michael Jackson on SNL. But a little context goes a long way. His appearance on Letterman’s fourth-to-last taping of the Late Show would be his last. After 20 years of hilariously memorable appearances on the show, MacDonald, knowing he wasn’t just saying good bye to a talk show host but his idol and kindred comic spirit, gave into the moment.

    “I know Mr. Letterman is not for the mawkish, and he has no truck for the sentimental,” he said. “But if it is true it is not sentimental, and I say in truth, I love you.” We’ve seen a lot of that vulnerability played out on the Late Show in recent weeks, from memorable appearances from Julia Roberts and Adam Sandler to heart-wrenching performances from the likes of Elvis Costello, Ryan Adams, Eddie Vedder, and Tom Waits, whose “Take One Last Look” cut right to the heart of Letterman fans the world round. It’s been hard lately to watch the show without realizing what’s being lost. Maybe we should have begun bracing ourselves for the inevitable some time ago, but now less than 24 hours away from his final monologue, Top 10 list, and desk-side chat, many of us still aren’t ready for Dave to leave.

    letterman mcdonald Goodnight, David Letterman: A Celebration

    But why? After all, it’s only television. Who is this formerly gap-toothed madman for whom the whole world has gathered together in praise? Why is he different, and why do we feel his imminent departure the way we do? You have to travel back to 1982 for the answer, but it’s one that availed itself almost immediately once Late Night took NBC’s airwaves. It’s hard to imagine now, but for many years Johnny Carson’s Tonight Show was the only game in late night. The whole country loved Johnny for all the long discussed reasons: he was charming, likable, and hilariously quick witted, the kind of guy you’d happily give up an hour of your day to each night. He invented late night’s monologue-desk piece-guest-band set up that still holds strong to this day, and for his first 20 years at the Tonight Show desk, America didn’t know any other way.


    Then on February 1, 1982, David Letterman, former comic, weatherman, and one-time daytime talk show host on NBC, pulled the tablecloth out from underneath the fine china, making a delirious mess of the Tonight Show’s tidy late night formula in the process. Late Night, from day one, was a subversive exercise in how far you could push the boundaries of television. Bill Murray’s now-legendary debut appearance on the inaugural episode, one rife with erratic comic tension between the wily guest and the somewhat-sheepish new host, would have never flown in Carson’s buttoned-up world of superficial talk with glamorous A-listers. But an hour later at half past midnight, there was room to play. The rules that preceded the show did not apply to Letterman’s anarchic talk show vision.


    Over the next decade, Letterman and his crack staff of writers and producers used Studio 6A as the world’s most fucked up comedy lab, one populated by monkey cams, stupid pet tricks, velcro suits, and bizarre gimmicks. Chris Elliott hung out underneath the seats. Shows were inexplicably taped in the hallway. An unsuspecting NBC page was once given $20 and a ticket to board a boat to the Carribean, provided he could get across town before the boat left in 15 minutes. Some guy named Larry “Bud” Melman handed out hot towels to passengers at the Port Authority Bus Terminal. Dave made gleeful use of weird average Joes like Rupert Jee, who succumbed to his every bizarre comic whim. Every July, watermelons rained from the roof of the GE Building. Every December, meatballs were knocked off atop Christmas trees with footballs.

    Every moment on Late Night smacked of an opportunity for comic reinvention, but bigger than the endless array of gags and stunts was Letterman himself. Just as his show reveled in defiant anti-comedy, Letterman was the quintessential anti-host, a lovable crank that itched at showbiz phoniness like a bad rash. Combative interviews with the likes of Cher, Crispin Glover, Charles Grodin, and others furthered Late Night’s identity as this angsty alternative to safe, cookie cutter chat shows, and word quickly got around that Letterman was not one to hassle.



    A maverick with a hair-trigger wit, Letterman gleefully took to incising his targets (other shows called them “guests”) with just the faintest detection of bullshit. This earned him a reputation as mean and bullish in some circles, and that’s somewhat fair. But a Letterman reaction was always an honest one, and that counts for something. When he laughed, you were funny. When he grunted or grimaced, his annoyance or displeasure was immediately made known. When he took you to task, you were deserving of it. Personable he wasn’t, but the millions of fans, soon-to-be comics, and late night hosts in the making who clung to Late Night like it was Gospel gladly overlooked likability for something much more rewarding: the sense of danger, unpredictability, and forthrightness that permeated through the show’s best moments.

    Letterman’s stock was at its peak when NBC suits were left to tap Carson’s replacement in 1992, and when they opted for Jay Leno to take the Tonight Show reins, the network’s loss was CBS’ gain. Dave grumbled and muttered his way through his final season of Late Night, taking plentiful parting shots at his employer on his way out the door, which he exited on horseback in June 1993. It was the perfect ending that captured the show’s bone-bred insubordinance, America’s late night hero leaving in the kind of grand, ceremonious fashion he’s always outwardly despised. The book had closed on one of the greatest tenures in television history. David Letterman, by any measure, owned the 1980s. But his transformation from late night upstart to the genre’s greatest living icon was only just beginning.

    the late show letterman Goodnight, David Letterman: A Celebration

    When he took the Late Show chair in August 1993, Letterman ditched his classic tennis shoes-khakis combo for stylish suits. But that’s about all that changed in the move to 11:30 p.m. EST. The Late Show was bigger than its predecessor, but hardly broader. Much to fans’ relief, Letterman didn’t tone down his edge for the sake of appeasing broader audiences. The show’s earliest years were peppered with unpredictable moments that echoed Late Night at its zenith, from Madonna’s profanity-laced appearance in 1994 to Drew Barrymore’s famous table dance a year later. The old dynamic was still very much in play, with Leno’s Tonight Show lobbing comic softballs to middle America and Letterman walking much closer to the edge. The fact that the two shows went head to head just fueled the dichotomy even further. Dave made a good run for a while, establishing his ratings-certified reputation as the King of Late Night for his first two seasons. But it wasn’t meant to last. Leno quickly usurped Letterman in the ratings, and the Late Show never retook the number one spot. Leno’s polished, likable everyman quality played better at 11:30 than Letterman’s irascible honesty.


    But ratings don’t tell the whole story. Despite losing the ratings war to the Tonight Show, Letterman aged gracefully, retaining his caustic edge while evolving into something Leno, and even Carson, couldn’t attain. He became one of the single best broadcasters in television history. He could still spar and take people down a peg when the opportunity struck, just ask Paris Hilton or John McCain. But as the 90s bled over into the 2000s, the Late Show’s best moments were marked by Letterman’s humanity, not his razor wit. His return from quadruple bypass surgery in 2000 didn’t pack the surrealist punch of his elevator races on Late Night or his days manning the McDonald’s drive-thru, but it was truly spellbinding television.


    However, Letterman’s ascent to America’s guiding television light was complete in the aftermath of September 11th. Days after the attacks, at a time when many were still too shaken and confused to put their pain into words, Letterman, along with other hosts, spoke for us all and helped guide viewers through the most difficult time in American history. When an emotional Dan Rather broke down during an interview on the Late Show, it was a moment that perfectly captured the fragility of a nation. Letterman took hold of Rather’s hand in an attempt to comfort the shaken news anchor as he cut to commercial. He might just as well have taken ours. Ten years earlier, David Letterman was maybe the last guy you would seek for comfort and guidance. Now here he was, doing his small part to help a scared nation heal itself one step at a time.

    Even Dave’s less than admirable moments, which seemed to catch up to him in his later years, were the stuff of great TV. When an extortion attempt laid his many infidelities out bare for the world to see, Letterman turned it into 10 minutes of riveting confession. It’s hard to imagine another celebrity in a similar circumstance choosing to tackle that shame and humiliation head on, especially in todays world where it’s easier to deny or keep your mouth shut. Instead, Letterman aired his laundry and came clean to a nation of millions, a moment of brazen honesty in a television medium that’s historically shunned it. More recently, a misguided joke about “treating a lady like a whore and a whore like a lady” fell miserably flat. There was no saving it and Letterman could do nothing to back out. And yet watching it you knew you weren’t going to find a moment like that anywhere else on television.

    david letterman classic Goodnight, David Letterman: A Celebration


    Maybe when all is said and done, that’s what we’ll miss. Not the Top 10 lists, great musical performances, or the uncomfortable exchanges between host and guest, but rather the experience of knowing you’re watching something real and significant in a TV world where everything else seems canned and superficial. In a recent feature on Letterman’s retirement that ran in Rolling Stone, Tina Fey lamented the legendary host’s retirement. “There is no one left to be scared of,” she said. “It’s all friendliness now.” Solid point. With all due respect to Jimmy Fallon, Jimmy Kimmel, James Corden, and the rest of late night’s new wave, there’s just too much kissing of the ring. Watching Betty White play flip cup is fun, but it lacks the kind of grandeur, humanity, and raw nerve that so many of Letterman’s best moments afforded us. He knows this late night empire that’s he’s spent 30-plus years crafting is no longer his world, and he’s generous enough to step out of the way. Now feels like the right time for him to bow out. His impulse to exit is real. Who has he ever been to deny that?

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