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?

    Top 10 Late Night/Show Performances

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    The format is simple: opening monologue, sketches and recurring bits, guests on the couch, and finally, a musical performance. But nothing was simple with David Letterman. The bands he brought on stage each night were a reflection of his passion to take risks and never settle for the easy out. From legacy acts delivering extended jams to unknown commodities making their nervous debuts, David Letterman has overseen some incredible musical moments. To pick only 10 is almost criminal, but if Dave can do it, so can we. Ladies and gentlemen, please welcome…

    10. Le1f – “Wut”


    Openly gay rapper Le1f’s hit single “Wut” shows off immaculate slang and speed, certifiable proof of unsung talent far more brazen in production tactics than some of his contemporaries. Amid a fraction of social networking controversy, Le1f eventually decided to one-up his Twitter rants on inequality for LGBT artists by performing on David Letterman’s titanic Late Show stage, one fateful evening. Say what you will, but this is significant, and we hope more independent and open-minded creators can follow suit come time for Colbert’s entry. –David Buchanan

    9. Sonny & Cher – “I Got You Babe”


    Does anyone remember Cher in bondagewear on a Navy vessel? Does anyone remember the skiing jokes by Eminem at Sonny’s expense? How about this song’s intentionally irritating co-star role opposite Bill Murray in Groundhog Day? Most people my age recall only these memories, but our folks reminisce far differently — to an age of disco music and dangerous divorcees, a time when the 1970s Sonny & Cher were variety TV stars with duets aplenty. By the 1980s, that turned into a very, very complicated relationship, yet somehow Letterman’s charm gives way to a surprise final take on the famous couple’s most infamously addictive hit single ever. It’s quirky, it’s awkward, but it’s important. So important. –David Buchanan

    8. Future Islands – “Seasons (Waiting on You)”



    It wasn’t supposed to be a big deal. The Baltimore-based synthpop band Future Islands made their network television debut on The Late Show, performing “Seasons (Waiting on You).”. They had four albums to their name, but were relatively obscure for a group gracing the Ed Sullivan Theater stage. What happened next was Samuel T. Herring dropping some serious dance moves, and the Internet taking notice. Even Letterman seemed awestruck by the dissonant radiance emanating from Herring’s body as he tore across the stage. There were memes and gifs and Tumblr posts galore, but more importantly, there was a band with a new found audience that included at least one very famous fan. –Zack Ruskin

    lovering pixies letterman e1432094269525 Goodnight, David Letterman: A Celebration

    7. Foo Fighters – “White Limo”


    Dave Grohl and co. had a long-standing demand toward Metallica to get heavy again, which inevitably led to Death Magnetic and lots of long, thrashy solos. Foo Fighters themselves, however, were two albums in for pop rock and needed a bit of reinvigorating also, culminating in the extraordinary victory that is Wasting Light. While simultaneously honoring the Beatles on Letterman, the Foos presented their single, “White Limo”, to a rabid fan base, and proved they could put their rubles where their rock was and shred out grunge like it was the 90s all over again. Thank you, 2011, and thank you, Letterman –David Buchanan

    6. Elvis Costello – “(What’s So Funny) ‘Bout Peace, Love, and Understanding”


    Elvis Costello is the Elvis we want, and the Elvis we deserve. He’s the geeky, bespectacled British analog of They Might Be Giants if two members became one and hired a backing band. And if we’re arguing for clout on a sense of humor, Costello’s opening monologue is a lighthearted introduction to himself with enough false bravado and self-effacing that one almost wishes he had his own late night hat in the primetime ring. Elvis Costello would never do that, though. Elvis Costello would just be Elvis Costello, and that’s what’s so funny about it. –David Buchanan

    5. The Beastie Boys – “Ch-Check It Out”



    No matter how varied the performance on the stage may be, every late night performance still follows the basic structure of a musical artist or group on stage playing a song. Leave it to The Beastie Boys to think outside the box and celebrate their beloved New York City by starting their song on the streets outside of the Ed Sullivan Theater, mugging for the camera as it pulls backwards. Their song of choice, “Ch-Check It Out,” won’t be remembered as one of the group’s best, but the energy behind this particular performance—MCA, Ad-Rock, and Mike D spitting bars as they barge through the maze of hallways backstage before bursting onto the Late Night stage—will live forever. –Zack Ruskin

    brian bell weezer e1432095155482 Goodnight, David Letterman: A Celebration

    4. Adele – “To Make You Feel My Love”


    Sometimes subtle is the most explosive choice. In 2011, Adele was skyrocketing to the kind of fame few can hope to ever achieve, let alone as a 23 year-old with two albums to her name, when she delivered a startlingly poignant rendition of her single, “To Make You Feel My Love”. Backed with only a piano and the hushed silence of a reverent crowd, the English singer-songwriter belted the bittersweet ballad while seated on a stool, the antithesis of a diva aside from a once-in-a-generation voice. It was pop. It was jazz. It was something sultry and sad and altogether wonderful. –Zack Ruskin

    3. James Brown – “Get Up (I Feel Like Being a) Sex Machine /There was a Time/I’ve Got the Feelin’”


    Let’s go back, all the way back to 1982, year one of Dave’s late night career. James Brown is the musical guest. Does he play one song? Of course not. Two? Close, but not quite. Three? Yes, that’s the ticket. Brown dominated the episode with blistering versions of “Get Up (I Feel Like Being a) Sex Machine”, “There Was a Time”, and “I’ve Got the Feelin’”. Aside from a bravado performance from the Godfather of Soul, Brown’s set was special for the way Paul Schaffer and the World’s Most Dangerous Band joined in. They were a more than adequate backing band, and Schaffer was feeling it. At one point, Brown starts in on the piano during “Sex Machine” and Paul simply stops and stares, enchanted with the moment. That’s music magic. –Zack Ruskin

    2. Bruce Springsteen – “Glory Days”



    When the flames from the Late Night War subsided, Jay Leno was the new host of the Tonight Show, and David Letterman was finished with NBC. Before he moved to The Late Show, he closed out Late Night with guest Tom Hanks and surprise musical guest Bruce Springsteen. The Boss had yet to appear on Late Night, and by way of introduction, Dave said simply, “So, better late than never: Bruce Springsteen.” The New Jersey rocker then launched into “Glory Days”, a cathartic moment that seemed to touch the usually stalwart Letterman and close a chapter in his already storied career. As the band built momentum, Springsteen leapt onto Paul Schaffer’s keyboard, a perfect visual representation of the chaos that had clouded Late Night in its final months and a worthy first send-off for Dave. –Zack Ruskin


    1. Warren Zevon – “Roland the Headless Thompson Gunner”


    Letterman is a notoriously diehard Warren Zevon fan. So much so that he very well may rival David Duchovny’s own Hank Moody. In 2002, Zevon was diagnosed with terminal mesothelioma, which signaled the end of an illustrious 12-album career, not accounting for live recordings. With death reaching his doorstep, Letterman urged the psychedelic bluesman to play for his audience of millions one last time, to which Zevon obliged, appearing as his only guest for the show’s hour-long airing. What followed was a revisit to Zevon’s most successful LP, Excitable Boy, and a folksy fictional biographical tune about a Norwegian gunman. David Letterman could never have gotten any luckier, and Warren Zevon — who died in 2003 — could not be more deserving of awe. We all will miss you both dearly. –David Buchanan

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