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Goodnight, David Letterman: A Celebration

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

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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.

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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

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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

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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

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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

33 Years, 33 Essential Memories

late show david letterman colbert Goodnight, David Letterman: A Celebration

For over three decades, David Letterman quilted a new patchwork of cultural touchstones that will extend long beyond his time on the television set. Irreverent bits such as The Top 10 List and Stupid Pet Tricks worked themselves into our water cooler language, while personalities like Paul Shaffer, Andy Kaufman, and even Bill Murray are now inextricably linked with Dave. In an industry where it’s easier to just become a company man, Letterman stood out from his peers. He was undaunted and unflinching. Letterman was comfortable tearing apart pop culture while teasing the rich and powerful, but he also was the first to admit to his own mistakes or share inspirational words in the aftermath of tragic events. No matter what the day had in store, Dave stopped by each night like a loyal friend and mentor to help us make sense of it all. In honor of this incredible life in show business, we’re taking some time to look back on 33 instances where David Letterman did it better than anyone else.

The First Carson Appearance

Here’s the first moment. Here’s where television’s David Letterman was born. On The Tonight Show with Johnny Carson, Letterman came in hysterically, making jokes about dog food, and toothpaste, and cereal, and really not much if you think about it, but it was Letterman all right, all caustic and witty and odd, and it was the beginning of 46 fabulous appearances on The Tonight Show from 1978 to 1993, including gigs as a guest host. Carson loved Dave, loved his style, and sense of humor, and wanted him back again and again over the years. -–Blake Goble

Bill Murray’s Bookends

Bill Murray and David Letterman are kindred spirits. They’ve each made careers by being the smartass kid in the back row who hurls wry comments and jokes at the hapless teacher struggling to maintain authority. Audiences everywhere knew they were in for a treat when these two wiseacres got together.

Murray’s appearances were unpredictable. He conducted interviews dressed as Liberace, a jockey, a padded out footballer, and a dignified gentlemen among others, while also beating up planted hecklers in the crowd, dumpster diving, and spray painting messages across Letterman’s new desk. In fact, we could write another list that’s nothing but Bill Murray highlights and still not capture all of the moments.

Murray was actually Dave’s first ever guest on the premiere episode of Late Night in 1982, and then turned up again as the first guest on The Late Show premiere in 1993. It’s now 33 years later and this comedic odyssey will come to an end with Murray appropriately dropping in as Letterman’s final guest ever. –Dan Pfleegor

The GE Handshake

In 1986, General Electric purchased NBC parent company RCA. Letterman, ever the good neighbor, decided to greet his new corporate overlords by personally delivering a fruit basket to the GE headquarters. A simple enough premise, but things did not go as planned. Instead, Letterman walked into a quagmire of red tape and fortune 500 confusion. Like a modern day Emperor’s New Clothes, he relished the chance to be the smartass kid who pokes fun at the king. He was stubborn, unyielding, and aware that these tense interactions with suits were a comedy goldmine for his working class fans. It was an incredibly bold move that established Letterman as a man of the people who was willing to stand up to anyone or anything that took themselves too seriously. The “GE Handshake” also entered the cultural lexicon as a symbol of the disconnect between big business and humor. Your move, Michael Moore. –Dan Pfleegor

Biff Henderson’s Landmark Remotes

James Jackson “Biff” Henderson, Jr., born October 3, 1946. Stage manager for The Late Show with David Letterman, American comedian, and proud owner of some of Dave’s finest location segments. He bugged New Yorkers on the streets, covered horse racing, Biff even groped a Larry King doll. Among the crew and local vendors that got screen time at Late Show, Biff was the king with the most consistently funny remotes. So cheers to Biff Henderson for keeping that show running all those years while being funny on camera. Fun fact missed until reading Wikipedia? His theme was “Milestones” by Miles Davis. Good taste, Biff my man. –Blake Goble

The Hands and Mind of Paul Shaffer

Paul Shaffer is a musical Renaissance man whose ever present smile, energy, and sunglasses were a reminder to the sometimes cantankerous Letterman that it was all going to work out. Shaffer’s background in show business made him a perfect companion for Dave. He worked on SNL for a number of seasons and even wrote the No. 1 Billboard hit “It’s Raining Men” all before joining Letterman as leader of “The World’s Most Dangerous Band” in 1983. The loyal Schaffer then followed Letterman to his new gig in 1993, establishing “The CBS Orchestra”, whom Schaffer lead to the very end. Thirty-three years together. That’s longer than most marriages.

Schaffer’s role on the show is also significant because his charisma and abilities allowed him to expand on the role of bandleader by growing into the de facto co-host — or at the very least, official hype man — after it was clear that he and Letterman could engage in witty repartee on just about any subject matter. Schaffer was also quick with the cues and seemingly picked the correct entrance song for each guests, which was apparent after watching most of them bow in appreciation to Shaffer before walking over to sit next to Dave.

And whenever a musical act stopped by the show, Shaffer was happy to assist as much or as little as they needed. But we all know the best performances were the ones that brought Shaffer and his full team into the song to help beef up the output with additional vocals, screaming horns, and that rich full orchestra sound. There’s never been a bandleader quite as versatile as Shaffer. And chances are there never will be again. –Dan Pfleegor

The Out-of-Control Animals

“Is that a lemur?! It’s a lemur, isn’t it!?”

The late night talk show host hanging with exotic animals shtick is as old as time, but when Letterman got to square off with peeing monkeys and vicious snakes, it was a hoot. Oh, like an owl landing on Dave’s head! Jack Hanna’s breathy, exhausting appearances as he rolled out what felt like a dozen animals per episode was the zaniest zoo you ever saw, and Letterman took on every animal with equal parts fright and curiosity. And he’d almost always ask if the damn things were lemurs. They weren’t lemurs, but thanks for asking, Dave. –Blake Goble

Rupert Jee’s Hello Deli

The Hello Deli is located right next to the Ed Sullivan Theatre. Its owner and operator, Rupert Jee, first appeared on the Late Show in 1993 during a segment called “Meet the Neighbors”. Letterman took a liking to the little sandwich shop and returned on numerous occasions. Sometimes Jee would help Dave run trivia on customers or read through the Top 10 List, but the highlights were the hidden camera pranks that dropped a bumbling Jee into everyday situations with a sarcastic twist. Letterman would feed lines to a wired-up Jee who basically went undercover to annoy normal people with tricks and awkwardness. Unlike future prank shows, where celebrities punk out their friends, Jee’s moments were funny because of the anonymity of the mild-mannered shopkeeper. It also carried on Letterman’s practice of bringing real life oddball characters onto the show, which is a tactic that inspires both Howard Stern and Jimmy Kimmel to this day. –Dan Pfleegor

The David Letterman Show (NBC)

Welcome to 90 wonderful episodes of The David Letterman Show! Originally aired on NBC daytime for a mostly domestic audience, clearly a target demo for Dave, Letterman’s first big show was a 90-minute laugh fest where he was getting his TV legs. The show premiered in June 1980, and was then cut to 60 minutes before its inevitable cancellation in October that same year. I mean, who wants to watch Andy Kaufman freak out during the day, let alone at night? But considering that The Chevy Chase Show lasted for all of 25 episodes, this was a great start. Still, it’s a fascinating beginning for Dave at hosting his own show, and everybody’s gotta start somewhere. –Blake Goble

The Quintuple Bypass Heart Surgery

In January of 2000, Dave got an angiogram that found arterial clogs. The feisty funny man, 52 at the time, was nervous given that his father had died of a heart attack at 57, and there was a history of heart disease in his family. According to People Magazine, Letterman didn’t want to wait. Walter Cronkite came on to Letterman’s show right before the surgery and assured Dave that his cardiothoracic surgeon was phenomenal. Quintuple bypass is scary. Cronkite’s assurances must have felt nice, that guy was all facts.

Dave was off the air, recovering for weeks. CBS aired reruns introduced by good friends, and special episodes with hosts like Kathie Lee Gifford, Bill Cosby, and there’s no point in going from there … those two? Anyway, when Dave came back on February 21st, it marked the dawn of a new era. A softer, somewhat gentler Dave. A grateful Dave, who even brought his medical team on the show to talk about everything he went through, and to thank. And, of course, Dave re-entering the Ed Sullivan Theatre, triumphantly, gave Dave one of his all time great punchlines: “Wait till you hear happened to me!” –Blake Goble

The Rise of Mitch Hedberg

The legacy Mitch Hedberg lives on to this day across social media status messages, YouTube compilations, and broken escalator signs worldwide. But the secretly troubled comedian may not have broken into the lovable arms of the mainstream had it not been for 10 incredible stand up appearances on Letterman. Starting with his first in 1996, these spots were always accompanied by big laughs from the audience as well as the host himself. Dave’s tearful chuckles and praises elevated the modest Hedberg’s status from zany stoner comic to universal humor factory. His nervous segments also cemented Hedberg’s reputation as an original voice whose observations could make four-year-olds and octogenarians alike laugh out loud. Mitch was one of the greats, and Dave’s kingmaker instincts recognized this fact early. Dave’s reaction after Hedberg’s first set says it all: “Take a bow, sir.” –Dan Pfleegor

Drew Barrymore’s Desktop Flash

Type in “Drew” in a YouTube search, and the first result to pop up is “drew barrymore letterman.” Maybe YouTube is fully aware of my affinity for classic Letterman clips, but still, this is one of Dave’s moments of pure comedy gold. And it’s all in the facial reaction. Drew Barrymore trotted out for Dave’s birthday. She had flowers for him. She had all the hallmarks of an overlong, manic Hollywood cool girl interview. She was fun and totally excited to be on the show. But around halfway through the interview, she offers to do a dance for Dave, and so she scales the desk, and whips her breasts out. Her giddy fist pumps, she’s like a kid learning about her own body (with creepy, sexualizing music from Paul).

But what makes the moment not so cringe-worthy, and really damn funny, is Dave’s almost W.C. Fields-like astonishment. His eyes bugged out, and his face was that of disbelief, complete with a dumb lug smirk, and he kept fidgeting with his jacket. Dave assured that the moment wasn’t about cheap laughs or being perverted, but rather about making it a self-aware, cute joke about a dirty old man getting all gee shucks over a young girl’s wiles. –Blake Goble

The John McCain Takedown

Despite wingnut claims to the contrary, Letterman did a good job of setting his personal politics aside throughout most of his long career. He’s welcomed guests from all over the political spectrum and won’t shy away from making light of any party or persuasion. Maverick Senator and perennial White House hopeful John McCain was one such politician, whom despite being teased, would still make regular friendly Letterman appearances. That all changed one day.

Late in the 2008 presidential race, McCain cancelled his guest spot at the last minute citing an economic crisis in Washington. Letterman was not happy, but understood the urgency, at least until he caught wind that McCain didn’t return to Washington and was still in New York for an interview with CBS’s own Katie Couric, whose studio was right by Letterman’s Ed Sullivan Theatre. Dave did not suffer this slight quietly and instead spent nine minutes going after McCain’s character and honor. He also cut to CBS’s internal camera feed to show an absentminded McCain being made up for his words with Couric. “Need a ride to the airport, John?!” mocked an irate Letterman, before bringing in substitute guest Keith Olbermann, who joined in the mockery over such weak excuses. –Dan Pfleegor

Rena Smaha’s Strange Monkeys

While this isn’t generally considered, like, a classic Dave moment, it’s easily got to be one of Dave’s craziest. It’s the kind of stuff you’d show your buddies while high in the ‘90s bootleg video days. “Have you seen this video, man? Dave’s absolutely afraid of a pair of reckless monkeys and their shady handler!” The whole segment shows Dave, at perhaps, his most unhinged, and unable to control the situation. When he shrieks that a monkey’s going to rip a vein out of his neck, it’s the sounds of a genuinely terrified person, and Dave’s generally the too-cool-for-school type. We’re not cheering for bloodsport, no. It’s a great moment because of how strange it is. –Blake Goble

The 9/11 Monologue

Letterman returned to the air a week after the attacks on Washington D.C. and New York. It was a somber time. On top of all the ideology and confusion, people didn’t know if life would ever return to some semblance of normalcy. Letterman’s role as a late night comedian and satirist helped get folks through a number of crises in the past. There’s just something about watching his show before bed that lets you know it will all be alright. But now was the time that the country needed Dave’s nocturnal reassurance the most.

Letterman’s own brush with death during his medical issues in 2000 prepared Dave to deal with such serious and heavy subject matter on the show. After all, his heart obstruction nearly killed him, but he still found a way to balance the serious with the silly. Taking a cue from Mary Poppins, Letterman delivered both the medicine and the spoonful of sugar. He acknowledged Mayor Giuliani, the firefighters, and the police officers for their sacrifice, while reminding his audience to never take these people for granted. He followed it up by admitting it’s difficult to be funny but ”Thank god Regis is here so we have something to make fun of.” –Dan Pfleegor

Letterman’s Friendship with Regis

It’s hard to put a finger on what’s so special about Dave’s friendship with Regis, but he kind of represents the best of B-team regulars on Dave’s show. On the recent CBS farewell special, there was a showreel for the likes of Stern and Simmons and Roberts and Hanks (everybody’s pal, really), all those celebs that have become synonymous with Letterman’s chairs. But it’s the George Millers, the Don Rickles, and all the other oddballs that just got along with Dave, but weren’t quite known as Dave star staples. But perhaps his best bud in the second slate of guests was Regis Philbin. When Regis was on, you knew the two would just kick it, have a good chat, and make for semi-decent TV. Like old pals. Be sure to find Philbin’s guest stint on the Late Late Show, where he got Letterman to appear for a good old-fashioned talk. You know, like a real talk show! –Blake Goble

The Hypocrisy of Bill O’Reilly

Party line pundits are a dime a dozen these days. But the ringleader of this modern era of blowhards is none other than papa bear Bill O’Reilly, a man who divides his time between leading Two Minutes Hate and writing non-historical fan fiction about Abe Lincoln, JFK, and Jesus Christ. It’s tricky to recall now, but in the post 9/11 era, a waterfall of patriotism made it seem treasonous to do anything short of parroting conservative talking points. But Letterman was unimpressed with O’Reilly’s condescending tone and decided to say what everyone watching was thinking: “You’re putting words in my mouth. Like the way you put artificial facts in your head.”

It was a moment of truth, which a humbled O’Reilly tried to spin as proof that the apolitical Dave was redder than a blushing Lenin. But everyone who saw the interview could gaze through this weak facade. Dave, having proven himself a reliable truthfinder for decades, pointed out this political hackery almost immediately, whereas O’Reilly, possessing the self awareness of a drunk uncle arguing politics the dinner table, could only seethe as his credibility floundered. Fun Fact: Both Letterman and O’Reilly engaged in extramarital affairs, but only admitted to it explicitly on their own show. –Dan Pfleegor

Dave’s Apology

Has a public figure ever been this sincere, or contrite? When a blackmail scandal broke out for Letterman, and a disgruntled ex-employee wanted to out Letterman for extra-marital affairs, Dave knew full well that it could ruin his career. So he did the smart thing by getting ahead of the scandal, but the ingenious thing was Dave taking to the camera himself to explain the situation, and deeply, honestly, asking for forgiveness. Eliot Spitzer didn’t play it like this. No celeb ever does, but Dave took a risk and admitted that he needed to make up for mistakes. Be sure to watch the complete video; it’s Dave’s most humane moment on air. –Blake Goble

The Top 10 Lists

The history of the Top 10 is disputed, unclear at best. It’s been around for roughly 30 years. Did Carnac the Magnificent last that long? It certainly was a little more offensive … “mystic from the East.” Yeesh. But the Top 10 has seemingly outlasted all the late night television gimmicks, and it’s probably had the highest batting average of the bunch. Every show, Letterman gave himself 10 chances to come up with a really great punchline, and more often than not, three of them were great. TAKE THAT FIVE QUESTIONS WITH CRAIG KILBORN! RIP FALLON’S LYP-SYNCHING! … Where were we? Yes, the Top 10 is terrific, and you’d likely get a laugh from them every night. Whether it were reasons for how cold it is in New York, or mocking the Yankees, or capitalizing on current affairs, the Top 10 was there to goof off about it. –Blake Goble

Mary Hicks’ Guest Appearance

Bill Hicks performed 11 times on Late Night but the gifted comic only made one final appearance on The Late Show on October 1, 1993. A dying Hicks, who kept his terminal pancreatic cancer private, wanted a last hurrah on network television before riding off into the sunset. This was not meant to be, however, as CBS’s Standards and Practices and a nervous Dave, trapped in the middle of a ratings war with Leno’s Tonight Show, decided to cut the set from broadcast after Hicks teased pro-life Christians during the routine. This material was tame compared to Hicks’ road work, but the scrapped set devastated the comedian and his legion of fans alike, especially after the young comic passed away just a few short months after. It was a Late Show lowlight for sure.

But then on January 30 2009, Letterman decided to right this wrong and invited the late stand up’s mother, the delightful Mary Hicks, on to the program to discuss what happened. It was a treat to watch the kindly Ms. Hicks speak so well about her boy. Letterman apologized profusely and even aired the entire routine uncut. It was a special moment that demonstrated Letterman’s willingness to humble himself by admitting mistakes, which is a rare quality to spot in most talk show hosts. –Dan Pfleegor

The Stunts, The Vandalism, and The Pranks Galore!

The sound of breaking glass is somehow appealing to the immature part of the mind. And thankfully Letterman is still a little boy chucking bottles in an Indiana parking lot just for the kicks. Over his career, he took this sophomoric energy and blew it up to a much larger scale. Whether he was hurling neon lights, bowling balls, and frozen turkeys off the roof, unleashing a camera mounted monkey into his studio, or nearly suffocating after dunking himself underwater in an Alka Seltzer suit, Letterman’s interest in crazy stunts and mayhem would go on to inspire an army of immature followers, from Tom Green to those wild boys in Jackass. It also motivated future hosts to get creative with their prop budgets and man on the street segments. –Dan Pfleegor

The Passing of the Torch

You always got the a feeling when you could tell if Dave actually liked somebody. We all know that thinly veiled disdain for Leno he’s been carrying for years. When he talks about “The Jimmys” in that New York Times exit interview, you can tell there’s more courtesy than care for the modern duo. But when Conan O’Brien and Dave get together, they’re like peanut butter and jelly. Cheese and crackers, really. They chat it up. They actually make each other laugh. When Dave made a surprise appearance on Conan’s show in the giant Bostonian’s early days at NBC, it was reminiscent of Carson showing up for Letterman at CBS, giving a sort of ceremonious thumbs up. The king of cutting edge comedy seemed to really like the prince of alternative humor. Dave supported Conan during the whole breakdown at NBC. Conan wrote the loveliest letter imaginable to Dave recently in Entertainment Weekly. The two deserve each other, more than any other late night hosts. –Blake Goble

The Late Night Wars

the late shift Goodnight, David Letterman: A Celebration

For years, Letterman was the heir apparent of Johnny Carson’s Tonight Show. Dave earned it, the fans wanted him to have it, even King Carson bestowed his blessing. But as we all know, it didn’t work out that way. NBC chose company man Jay Leno and Dave had to settle for a move to CBS, leaving his former Late Night gig in the hands of a young whippersnapper named Conan O’Brien. Never one to go quietly into the night, though, Dave would pepper his own shows with shots at Leno and NBC alike for years and years.

We thought the rest was history, but like the postscript of World War I, another conflict was sure to arise. And it did, in the form of Leno once again manipulating on-air personalities and executives alike to get Conan taken off a struggling Tonight Show so that he and his chin could rule the day once more. It felt tragic, but it also offered a golden opportunity for Letterman, Norm Macdonald, and Howard Stern to revisit their hard feelings and jokes about the duplicitous Leno all over again, much to the delight of fans who thought Jay should have never landed the hosting job in the first place, let alone twice.

Bill Carter penned two incredible books about these backstage dealings and betrayals. The Late Shift and The War for Late Night are now essential reading for fans of the medium, as well as anyone who might one day cross paths with the wily Jay Leno. –Dan Pfleegor

The Late Show (CBS)

To hell with NBC! Dave didn’t even want Johnny Carson’s stinkin’ show anyway!

… oh who are we kidding, Letterman’s snubbing by NBC stung, and lingered for years, but the history books will look back at The Late Night Wars, a fraught event in modern history, and they’ll declare Letterman the victor the second he turned himself around at CBS. Sure he’s never had Leno’s ratings while at CBS, but he never had to pander either. Letterman didn’t play the favorites, he got to make a TV show his way, in his style. He still got the edgier, hipper, and altogether more entertaining program on the air in the form of The Late Show, and Letterman didn’t take long to find his voice at CBS. Did anyone give Leno an Emmy for his 10:30 p.m. show? –Blake Goble

Andy Kaufman vs. Jerry Lawler

Andy Kaufman’s long streak of defeating women wrestlers in the squared circle came to an end the night a cocky young superstar named Jerry “The King” Lawler put Kaufman in a pile driver, ruining the streak, nearly taking his life. Kaufman, wrapped in a litigious neckbrace, chose Late Night as the forum to confront Lawler about these misdeeds. It almost started civil but soon devolved into a profanity laced tirade after Lawler met Kaufman’s gripes with an open-handed slap that knocked the comedian out of his chair.

You can tell on replays that the audience was never quite sure if what they were witnessing was real or not. There was hate in both men’s eyes, there was strong language, and there was even some coffee throwing. Amid the confusion and hostility, Letterman found his moment, “I think you can use some of those words on TV, but what you can’t do is throw coffee.” It brought the house down.

People continued to speculate for years on what exactly went down that evening. In the end, it turned out to be another elaborate Kaufman prank. Jim Carrey decided to revisit the incident while filming the Andy Kaufman biopic film Man on the Moon. During the Letterman takes, Carey as Kaufman wormed his way under Lawler’s skin. When the time came to deliver the slap, Lawler didn’t hold back and hit Carey with everything he had. Carey responded out of character by threatening to sue Lawler. Kaufman, now in heaven, looked down content that his prank found new legs. Oh, Andy! –Dan Pfleegor

Dave’s Mom

There’s something so innately Midwestern, and homey, about Dave’s sense of humor. Tina Fey once descbribed Dave at his Kennedy Center honoring as a sort of “goon from Indiana.” But that goon has a mother, and he loves her. Dorothy Mengering is her name. He loves her so much that he gets her to show up for all sorts of great bits. The comedy of putting a sweet old lady in silly situations. She asked Hillary about speed limits in Connecticut. Dave’s Mom did correspondence from multiple Olympics. She hung out with Donald Rumsfeld. But best of all, she was a fixture around the holidays, sharing pie recipes and cracking wise about how she’s gonna be drunk on Old Milwaukee’s after recording. Thanks, Mom, er, Mrs. Letterman. –Blake Goble

The Crispin Glover Incident

In 1991, an indie film called Rubin & Ed was released starring Crispin Glover and Howard Hesseman. Glover starred as a plat-formed, long-haired recluse, going on a journey to find the perfect place to bury his cat. Twee indie films, dude. Well, apparently, Glover was in character, he brought his nutty Rubin Farr character from the movie on the David Letterman’s talk show.

Unbeknownst to Dave.

In 1987.

And he stammered his way to nearly high-kicking Dave in the face.

In a stunning bit of glib comedy, shutting down the entire hair-brained, soon to be infamous shtick, Dave stepped, walked out, and said, “I’m going to go check on the top 10.”

It has to be one of the biggest, and best “uhhhhhhhhhhhs” in TV history.

Three years later, when Glover showed up on Letterman, he looked incredibly dapper, lean, he was coherent and excited to be there to talk to Letterman.

But best of all, Glover’s entrance music was “Kung Fu Fighting.” –Blake Goble

The Genius of Chris Elliott: Fancy Lad Writer, Eagle Hearted Performer, Cabin Boy

Chris Elliott joined the writing staff of Late Night in the mid 1980’s and went on to create some of the show’s more kooky sketches and characters. He would emerge from the audience as a crazed fan, invented bizzaro world characters for film parodies, and even ate dog food live in order to make Dave laugh. You could tell the host saw a bit of himself in the supercilious Elliott. Perhaps that’s why Dave turned up for a rare silver screen cameo in Elliott’s cult classic “Cabin Boy”, which was directed by former Late Night writer Adam Resnick. Letterman’s role in the film is tiny but his grin is wide as he shoots off his mouth and emasculates Elliott’s silver spooned protagonist. “Hey, would you like to buy a monkey?” –Dan Pfleegor

Dave’s Taco Bell Visit

Sure, the location stuff is easy enough. Stick Dave into a common location and let his eccentricity flourish. It’s a big win. Conan perfected it, but Dave practically invented it. Dave was great wrecking McDonald’s drive-thrus, both while in his car and manning the store window. He was good running around L.A. with Paul or Zsa Zsa Garbor. But arguably his zaniest, most indelible moment outside the studio was when he took over the drive-thru at a Taco Bell in Jersey in 1996. While the McDonald’s stunt is the legend, the Taco Bell is the secret winner. Dave drags out every conversation, and each line is gold. He invites patrons to suck on the fountain drink machine, offers overly expensive food, confesses to getting over the stomach flu, and, perhaps funniest and most left-field of all, bemoans losing toes in a lawn-mowing accident. Because that’s what you want to hear when getting fast food. –Blake Goble

The Stupid Pet Tricks and Kid Scientists

Despite wise words to the contrary, Letterman thrived in the off-the-cuff awkwardness that came from collaborating with showbiz’s two least popular partners. These bits usually went off the rails early, much to the delight of a wisecracking Letterman, who once debated a kid scientists over the correct pronunciation of the word “the”. Here, the kid chided and corrected Letterman’s use of “thee” instead of “thuh” when introducing the piece. Laughter over the child’s boldness filled the studio and then erupted into pandemonium after Letterman informed said kid there may not be time left to get to the “thee” experiment. –Dan Pfleegor

Uma. Oprah.

Yes, everybody’s always making fun of this moment for Dave. It’s been called one of the worst Oscar hosting gigs in years, but come the hell on. Do you really need more hackey Bruce Vilanch jokes told by a manic Billy Crystal? And the dance numbers, good lord, those are the worst. Or, or, would you rather have a host at least try to do something different and, in essence, jab at the industry he’s working for and in, because, why the hell not?

Actually. No. To prove Dave was strangely great, try this out at home, preferably with other people around. Repeat after me.

Uma.

Oprah.

Uma.

Oprah.

There, wasn’t that fun? –Blake Goble

Sorry You Couldn’t Be Here Tonight, Joaquin

I’m Still Here was an asinine event, a mumbly Joe riff on the sycophantic nature of vanity and celebrity scribbled by Casey Affleck and Joaquin Phoenix. Or rather, it was a stupid, overlong joke that rendered Phoenix incomprehensible to the public. And, oh boy, did Dave have fun with that. You can tell when Dave respects, or doesn’t like a guest. But when they annoy him, well, the two front teeth are bared and Dave sinks right in. His interview with the stubborn, “performance artist”-mode Joaquin Phoenix was Dave at his meanest, but only because Phoenix was so, so very deserving of that. And in Joaquin’s Phoenix’s little spoof experiment, Letterman easily got the last laugh. –Blake Goble

The Bristol Palin Joke

Let’s take a moment to analyze this dumb, really dumb joke Letterman made in 2009.

“Sarah Palin went to a Yankees game yesterday. There was one awkward moment during the seventh-inning stretch: her daughter was knocked up by Alex Rodriguez.”

Sarah Palin, Alaskan nut that almost nabbed a pair of keys to The White House, was pissed about that. She fanned the flames, thought it was a joke about her then 14-year old daughter, not the unwed 18-year old one with a small child. Oh sure, the joke was cheap and a bit mean, but in the public domain, she was more-or-less fair game. What came of it was endless discussions about that modern boondoggle we keep calling the state of comedy. It was a dumb joke, sure. But what the hell is in good taste anymore? It now feels like the first piece in an endless series of debates about humor and context that keep getting testier. We’re not on any side here. It just feels fitting that Dave turned into a latter day Lenny Bruce for a minute there. The guy just wanted to throw crap off buildings! –Blake Goble

The Constant Enigma of Larry Bud Melman

Throughout the 1980’s, Larry Bud Melman was one of the most recurring characters on the Late Night set. He was a squat, white haired old man who wore black glasses and spoke with a mockingly thick lisp. It didn’t hurt either that the TV character was portrayed by real life character Calvert DeForest, whose dramatic flair and oddball personality left Letterman fascinated. Viewers could not quite tell what was real and what was pretend. And that’s exactly how Letterman wanted it.

Unlike other made up personalities, Melman’s didn’t have an official role or even a signature sketch. Instead, he was utilized as the world’s oddest five-tool player, emerging from the audience to shout at Dave mid show, or out on the street conducting amateurish interviews where he famously lacked the skills needed to handle a mic properly, or even just appearing in costume to prattle off in a series of bizarre monologues and sketches.

Melman was Dave’s go-to weirdo, certain to inject any dull segment with a whole lot of offbeat and unconventional charm. DeForest passed away in 2007, but his legacy as one-of-a-kind comedic performer lives on and continues to inspire the late night landscape. Jimmy Kimmel’s parking lot security officer Guillermo Rodriguez would agree. –Dan Pfleegor

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