For most of the history of television, the barrier to syndication—and to profitability—has been 100 episodes. The shows that have made it to that mark are an unusual group. Many were big hits. Some found small cult audiences. Still others just hung on as best they could and never posted numbers quite low enough to be canceled. In 100 Episodes, we examine the shows that made it to that number, considering both how they advanced and reflected the medium and what contributed to their popularity. This entry covers Late Show With David Letterman, which ran for 22 seasons and more than 4,000 episodes between 1993 and… this Wednesday night.


In the May 1985 issue of Esquire magazine, David Leavitt published “The New Lost Generation,” one of the first pieces of literature associated with what would come to be known as “Generation X.” In it, the then-22-year-old wrote, “The voice of my generation is the voice of David Letterman.” Leavitt was referring to the late-night talk show host’s heightened sense of irony, which took the gushing language of the television business and delivered it with a thin smirk, with two raised eyebrows serving as quotation marks, signaling to the listener that the speaker was hip to his own shtick.

That exact tone made Late Night With David Letterman a cult hit when it launched on NBC in 1982. Yet even though the college kids who grew up with Late Night worked their way into positions of power and influence by the 1990s, Letterman’s reputation for being flip and sarcastic still led many to question whether he could ever succeed at 11:30. Now, 22 years after he launched Late Show With David Letterman on CBS, one of the most important comedians of his era can step down knowing that he’s proved himself—even if it was a rockier trip than he might’ve expected.


Because Letterman is retiring this week from late-night—and not just leaving Late Show—it’s hard to avoid talking about him in terms of his entire career, including that decade at NBC where he revolutionized the medium. The Late Night Letterman was part smartass local DJ, part Ernie Kovacs. He liked to play with the medium itself—gradually flipping the picture 360 degrees during one episode, for example, or doing an entire show from his office—but there was rarely any genuine “aw shucks” enthusiasm to his hosting style, not even when he’d throw objects off a building or run stuff over with a steamroller. He’d chuckle, then flash a knowingly phony smile at the camera, leaving the audience confused as to whether they were actually meant to enjoy what they’d just seen.

It’s hard to describe the 1980s version of David Letterman without making him sound like what Cher once called him on the air: “an asshole.” But Late Night back then was genuinely exciting and innovative because it was so hard to pin down what exactly it was supposed to be. Letterman assembled weirdos and wild ideas that belonged more on public access, and he gave them a national forum almost as though he wanted to prove that nothing on TV was all that important.


The Late Show Letterman was different, and has continued to change between 1993 and today. Even though he carried over a lot of the core elements of his 12:30 NBC show when he moved to 11:30 on CBS—Stupid Pet Tricks, the Top 10 list, his bandleader Paul Shaffer—Letterman also rolled into the new network with the clear intention of proving to his old bosses that they were idiots to let Jay Leno take over for Johnny Carson as the host of The Tonight Show. Letterman started delivering his monologues with more confidence. He cut down on the absurdist gimmicks. He did man-on-the-street segments where he came across more as puckish than aloof.

The tweaks worked—at first. For nearly two years, Letterman handily beat Leno in the ratings. In 1995 he was asked to host the Academy Awards, which was a major statement, given that the Oscar gig once belonged to Carson. The 1995 paperback edition of Bill Carter’s book about the Letterman/Leno rivalry, The Late Shift, ends with an epilogue that notes how The Tonight Show had begun to close the ratings gap a little, but Carter still declares CBS the victor in the mid-1990s late-night wars, ending with a small salute to “the man who continued to rule late-night television—America’s host: David Letterman.”


But by the time the revised edition of The Late Shift hit bookstores, Leno had taken the lead back, permanently. Multiple factors turned the tide: CBS’ programming started floundering just as NBC was riding high with Friends, Seinfeld, and ER; and Leno landed some high-profile guest-bookings, right around the time that he was filling The Tonight Show with dopey, crowd-pleasing jokes about the O.J. Simpson trial. Meanwhile, Letterman was still Letterman, never really wired to become the most popular personality on television. (Even his Oscar-hosting episode didn’t go so well, though to be fair that job has flummoxed almost everyone in the decades since.)

So when we talk about the end of the Letterman era or even the end of the Letterman Late Show, it’s important to remember that the majority of his time on TV was not spent as the clever young upstart that he was on NBC, or even as “America’s host” on CBS. From 1995 to now, he’s evolved into someone at once much crankier and much more exposed. He’s come back from life-threatening heart problems, an embarrassing sex scandal, and multiple efforts by the right-wing media to paint him as a mean-spirited leftist. Gradually, he’s grown into his role as the mildly bitter also-ran who speaks his mind.

Over the last decade in particular, Letterman’s been at his best not standing in the front of the stage reading jokes off cue-cards, or playing master of ceremonies for some goofy stunt, but rather just sitting at his desk, speaking off the cuff in the stretch of the show between the monologue and the introduction of the first guest. Like Jack Paar in his Tonight Show heyday, Letterman has become a spellbinding raconteur, telling long, self-deprecating stories about his everyday pet peeves. When he’s on a roll, sometimes he even ignores his time-cues and keeps going, knowing that whatever he’s saying will be more entertaining than any movie star with a picture to promote.


That ability to just sit and riff, with no apparent plan or endpoint, is something that still sets Letterman apart from the current generation of late-night hosts (although Craig Ferguson could do it well too when he hosted The Late Late Show, and it’s hard to say yet what Stephen Colbert will be like as Letterman’s replacement). Each of today’s hosts has strengths of their own that Letterman can’t match, be it their keen understanding of social media or—in the case of Jimmy Fallon and Seth Meyers—their refreshing niceness. But Letterman could always counter that with a physical presence unlike any of his competition, with his unruly hair, gapped teeth, and larger frame. He’s not significantly taller (or wider) than any other host, but either because of the camera angle, the Late Show set, or the way he carries himself, Letterman just looks bigger. The combination of his ungainly size and his gift of gab gives him a unique kind of charisma.

What this older Letterman has in common with his younger self is a genuine affection for venerable broadcasters: the kind who could always fill an hour or more of airtime a day whether they had any prepared material or not. Some of Letterman’s favorite guests over the years have been the ones who tell great stories (like Norm MacDonald), or can be entertainingly odd (like Bill Murray), or are just off-handedly charming (like Jennifer Lawrence). Letterman has seemed fascinated by these folks, and would keep inviting them back as though he were trying to crack the secret to their ineffable watchability. He was drawn to them in the same way that he gravitated to certain phrases that sounded like they could’ve come out of the mouths of small-market TV announcers circa 1962. Letterman could say “wake the kids” or “please, no wagering,” or even “German potato salad” with a certain practiced pleasure, as though he were humming the words to a favorite song.

Letterman’s sour overtones and his embrace of the antiquated could be unappealing at times. He sometimes treated non-celebrities too much like stooges in his comedy routines—especially if they had foreign accents or strange-sounding names—and as with a lot of comedians of his generation he used to be way too comfortable with lazy gay jokes. He’s also had a hard time disguising his boredom with some guests, or even with some of his own comedy routines. His energy has flagged noticeably in the later years.


Plus, the elusiveness of his 1980s persona has persisted to a large extent, such that when Letterman tried in the CBS era to get Oprah Winfrey on the show, she dodged the booking because, as she later said, “I didn’t know if you were being serious if you were doing your Dave thing.” He scared off some potential guests who worried that they’d give him their most sincere effort and he’d turn it into a running joke. (Which he just might’ve: Just ask Mandy Patinkin, who once sang his heart out for Letterman and then saw his performance excerpted and mocked on the show for weeks.)

But Letterman can be plenty sincere himself. He’s frequently gushed over athletes, and whenever a musical act would give a great performance on Late Show he’d talk them up on the stage immediately afterward and then again when they were inevitably invited back to do another show. Letterman won praise too for the way he handled his first telecast back after 9/11, where he spoke for America and for New York with an eloquence and compassion that he likely wouldn’t have been able muster in his Late Night days.

When Late Show With David Letterman signs off on Wednesday, its host will have done more than 4,000 shows, which is a lot for a person who once seemed to find everything in showbiz inherently dumb. But Letterman has never rolled his eyes at anybody in the entertainment industry more than himself. Whenever he’d tap his head, look into the camera, and say, “There is no off position on the genius switch,” he was making fun of his own license to broadcast just about anything that he wanted into millions of homes, all because he’d duped a major network into giving him his own TV show long, long ago. One thing Letterman learned early is that people on television tend to stay on television, if only because everyone assumes they knows what they’re doing.

If there’s been a consistent “voice of David Letterman”—from NBC to CBS, Late Night to Late Show, 1982 to 2015—it’s the voice of a man who’s a little worried that he’s wasting his audience’s time, but not worried enough to stop himself from spending five minutes on the air trying to find out what will or won’t float in a giant tank of water. That’s the generation Letterman still represents: one that’s cautious but still curious, and smart enough to appreciate the true value of something stupid.