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Letterman’s Last Great Moment

The last of the late-night titans announces his retirement

The old man set it up masterfully. He mentioned that his 67th birthday was coming up and waited for the “APPLAUSE” sign to flicker off. Sixty-seven. He’d been hosting a late-night show for half his life, he realized, so he grabbed an index card and counted up the shows. When he mentioned making more than 4,000 shows for CBS, everyone clapped like trained seals, because that’s what David Letterman’s audiences were trained to do. They thought they were getting an I can’t believe how many shows I’ve done bit. They had no idea what was coming.

Once upon a time, NBC Dave flipped the talk-show format upside down, re-created it and turned it into something else. You never knew what you were getting from night to night. He turned his staffers into running characters, answered letters from viewers, wandered into his audience for bits, brought cameras outside his studio to explore the hallways. For guests, he gravitated toward up-and-coming bands, quirky celebrities and comedians looking for their big break. If he found chemistry with someone — like Teri Garr or Jay Leno — he’d bring them back over and over again. He shined most with his revolutionary pretaped bits, like the time he wandered into the “Just Bulbs” store and harassed them for shades, or when he tortured everyone working for a McDonald’s drive-through, or his fake “after-school” special about a little kid finding out that an awful show called Voyagers had been canceled.

That version of Letterman was something of a tortured artist. You always felt like he felt he was a failure, that his show would never amount to anything, that within a few months, he’d get canceled and everyone would say, “Well, at least he tried some stuff.” At times, he couldn’t hide his disdain for a boring guest or a comedy segment that failed; he was always the funniest whenever it happened. He’d even turn on his audience whenever it applauded something unworthy. You could feel him bristling.

How could you applaud that? Stop it, just stop it.

Once Late Night took off and Letterman’s star ascended, it became harder for him to be self-deprecating. You don’t get celebrated on magazine covers for being a massive success if your show sucks. You don’t have a six-month waiting list for tickets if your show sucks. Eventually, he blossomed into a bigger, broader host, a real broadcaster, the next Carson … only he foolishly assumed that he’d succeed Carson without locking it down contractually. His old buddy Leno swooped in and stole the show away, a strangely seismic moment immortalized in Bill Carter’s excellent book The Late Shift, as well as an equally entertaining HBO movie with the same name. A hardened Letterman limped over to CBS, still devastated over losing The Tonight Show, determined to destroy Leno in the ratings. He broadened his show in subtle ways, guessing that signature bits, a roomier theater, A-list guests and constant applause would make his show more accessible. And for a while, he was right.

To everyone’s delight, Letterman grabbed first place for about 18 months. Leno closed the gap by shamelessly emulating Letterman’s show, even rebranding Letterman gimmicks like “Small-Town News” and “Stupid Human Tricks” as “Headlines” and “Don’t Try This at Home.” And Leno tirelessly networked with local affiliates, something Letterman never bothered to do. Everyone who loved comedy, and by extension, Letterman, was absolutely appalled when Leno finally passed him. What did this mean? What did this say? Was this a reflection on America itself? Were people really that dumb?

For a while, we dismissed Leno’s achievement because he leveraged a better brand and a more popular network. But when CBS started trouncing NBC, Leno kept winning. Letterman would always be second. Maybe that’s when he gave up. These last few years, CBS Dave stayed on autopilot 90 percent of the time. The constant clapping told you everything you needed to know. NBC Dave would have detested it. CBS Dave didn’t care.

But on Thursday night? Retiring Dave was going out his own way. No more gimmicks. He begged the audience to stop clapping. Practically yelled at them.

No more clapping. Please.

Everyone stopped clapping. They listened to him count up every show for 33 years — more than 4,000 for CBS, nearly 2,000 for NBC, and 90 for his ill-fated morning show. Close to 6,000 in all.

Suddenly he was telling a story about his 10-year-old son. They were outdoors one weekend and noticed an incredible bird. Was it an eagle? Was it something else? They couldn’t figure it out. They snapped a picture and searched on the Internet. Nothing. Letterman went to work the following day and asked his staff for help. They finally came up with the answer — or, what they thought the answer was. A bald eagle. He went home and excitedly told his wife. She heard the answer, then asked him blankly, “So who’d you have on the show?”

Everyone laughed. They didn’t catch Letterman joking that the moment made him wonder if it was time to leave, or how he derisively worried about becoming an old man who obsessed over birds instead of running a network show. If you’ve been following Letterman these past few years, you know his son was the greatest thing that ever happened to him. That bird story was really about being a father, about the day-to-day stuff that makes you realize your kids matter more than anything else. You begin your life and it’s exciting, and then it starts to get boring, and then your kids show up and you get to relive everything through them. The point of the story wasn’t the bird. He wouldn’t have cared about the stupid bird 10 years ago; he only cared about his show. Everything had flipped. Even his wife couldn’t see it. That was the point.

Her response triggered … something. It made David Letterman wonder if it was time to step down. When he admitted as much on Thursday night, everyone laughed nervously. They were feeling this might be something bigger now. He mentioned telling his son about wanting to spend more time with his family, followed by his son answering, “Which family?” More laughter. He mentioned calling his boss, Les Moonves, before that night’s show. They always had a great relationship, Letterman said. They’d always discussed the timing of this moment. And now, that moment was here.

“I phoned him just before the program,” Letterman recounted, “and I said, ‘Leslie, it’s been great, you’ve been great, the network has been great, but I’m retiring.’”

Wait …

What?

You could hear Paul Shaffer ask in the background, “This is — you actually did this?”

“Yes I did,” David Letterman said.

And what followed was one of my favorite television moments ever. Just emitting those three words — Yes I did — briefly sapped Letterman’s energy. Like he couldn’t believe they finally came from his mouth. Nobody in the theater made a peep. There was stunned silence. Two solid seconds of quiet felt like two hundred.

Letterman stared into the camera with a classic deer-in-the-headlights gaze, with every conceivable emotion in play: tears, sniffling, laughing, you name it. He settled on an exaggerated smile. Letterman always had that great, goofy, distinctive face — squished nose, gap between his front teeth, perpetually ruffled hair — which he used to enormous advantage over the years. This particular grin disarmed everyone in the theater. It was silly and heartfelt and astonished and sentimental and everything else it needed to be. It was perfect. It made them laugh.

Suddenly, it wasn’t so awkward anymore. Paul overreacted for effect and joked about calling his accountant. Letterman announced that he would leave in 2015, finally allowing him and Paul to get married. (That brought the house down.) He thanked the staff, the band and the audience. Everyone stood and cheered. They went to commercial. The spiritual king of late night was stepping down, and even better, nobody in the room saw it coming. I can’t remember another 10 minutes of television quite like it.

♦♦♦

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Maureen Donaldson/Getty Images

After Johnny Carson retired in 1992, David Letterman became the king and stayed the king, even as his show transitioned from antiestablishment to establishment. Leno drummed him in the ratings without matching Letterman’s relevance; he never mattered as much as Letterman did. We forgave Letterman for losing interest over the years, for never filming bits anymore, for clearly not working as hard as he used to, for chugging along because he couldn’t think of anything else to do (and maybe for the paychecks, too). Even an embarrassing sex scandal couldn’t ruin his legacy; he handled the ensuing fallout so effectively that, five years later, people barely remember it.

As Letterman became older and older, those human moments distinguished him. You wanted to watch him after 9/11. You wanted to grieve with him after Carson passed away. You wanted to hear him admit that heart surgery was scary, that he felt humiliated when private demons seeped into his show, that it pissed him off when John McCain canceled on him at the last minute. Candid Letterman was always better than Candid Anyone Else. When Kimmel and Fallon started thumping him in the crucial 18-to-49 demo, Letterman held one trump card: He’s the only late-night host who elicits the same respect from guests that Carson did. Even Jon Stewart can’t say that. We know celebrities appear on late-night shows to promote themselves; it’s part of the deal. They went on Letterman’s show to impress him, to win him over, and that was always the difference.

Quick tangent: When I was 15 years old, Letterman took his NBC show to Los Angeles for May sweeps. Back then, my four guys were Larry, Eddie, Bruce and Dave. They shaped my personality, my sense of humor, my outlook on life, everything. When I heard Carson was appearing on one of Letterman’s L.A. shows, it became Letterman’s unofficial Game 7. Johnny Carson was the king. He didn’t go on other people’s shows. This was Letterman’s ultimate vindication, and by proxy, losers like me felt vindicated, too. I had been watching since Year 1. That NBC show lifted an imaginary rope and allowed me into a little club, the Funny Club, created for the people who understood comedy better than everyone else. Unknown comedians like Seinfeld and Leno and Keaton and Hanks and Eddie came on and made me laugh. Chris Elliott lived under the stairs. Paul Shaffer did Paul Shaffer things. I loved all of it. Someone created a show specifically for me.

And now, my guy was hitting it big. I spent the week devouring those L.A. shows (they were especially great, just the best he could do) and worrying Letterman might fuck up the Carson interview. Nobody revered Carson more than Letterman did. This was the biggest moment of his career and he knew it. Carson walked out carrying his own desk — just a terrific gag — and they went back and forth, and Letterman held his own, and Carson walked off. You left that show thinking, Letterman has been blessed by the Late-Night Pope. He blew up right after that. After Carson retired, only Letterman intimidated guests with his fame and talent, and later, everything else he came to mean. It’s probably not happening again.

Even after I stopped watching Letterman regularly, like so many others, I always liked knowing he was still there. Conan grabbed his “cool” corner first, then Stewart hijacked it for good (and graciously shared it with his buddy Stephen Colbert). But the multiyear Leno-to-Conan-to-Leno debacle kept Letterman relevant, if only because he seemed classier and more impressive by comparison. In 2014, “Jimmy vs. Jimmy” replaced “Jay vs. Dave” as late night’s ongoing narrative, with Fallon unexpectedly thriving by tapping into a new generation of Internet-savvy viewers. Fallon gushes over guests, plays mindless games with them and basically acts like they’re sleeping over in his bunk bed. He gravitates toward ideas that might catch on virally, like Kevin Bacon becoming the Footloose guy again, or Arnold saying “Get to the choppa.” It’s a relentlessly happy, well-structured, well-produced show built around a talented performer who doesn’t want to have a coherent conversation. With anyone. Nobody will ever fear going on Jimmy Fallon’s show. That’s the way he wants it.

In retrospect, NBC played the chess board brilliantly. After Kimmel started stealing younger viewers from the creaky Jay/Dave corner, NBC moved proactively, sending Leno packing and leveraging February’s Winter Olympics into weeks of mega-attention and mega-promotion for a Leno-to-Fallon transition. When you include the Lorne Michaels/SNL/A-list celebrity infrastructure already in place, Fallon had an overwhelmingly good chance to succeed from day one. (If there’s been a lost story line here, it’s that Conan O’Brien squandered those same advantages four years ago. Instead of staying in New York with Lorne, he moved to California and stupidly left the Lorne Machine behind.) Now we’re already thinking about the Next Next Guy — within 12 hours of Letterman’s stunning announcement, names like Tina Fey, Neil Patrick Harris, Ellen DeGeneres and even Conan were being thrown around for his job. I will spare you the suspense — it’s going to be Colbert. Well, unless he has three more Twitter debacles or something. He’s getting that job.

And if this wasn’t interesting enough, you have my old boss, Jimmy Kimmel, battling the following obstacles: a still-surging Fallon; Letterman’s farewell year; Colbert’s eventual takeover; and ABC’s Dumpster fire of a prime-time schedule. Kimmel spent his first decade on ABC surviving — barely — before breaking ground with a video-heavy monologue, and later, by turning YouTube into an ongoing advantage. Just six months ago, Letterman’s biggest fan had the best chance of anyone to become Letterman’s spiritual successor. Can Kimmel’s 21st-century version of the Carson/Letterman model translate to first place? Can he ride out Fallon’s honeymoon phase, especially with Fallon working that same viral-friendly corner so well? And what if late night is skewing sillier in general? What then?

A good example: Last Wednesday, Kimmel ran a candidly entertaining chat with President Clinton, the kind of interview that Letterman would have done in his prime. Guess what. Fallon still beat him. Do viewers even want to watch quality interviews at midnight anymore? Should every segment skew shorter? Should late-night shows flood us with bits/jokes/games/songs/sound bites/videos/pranks/songs hoping any catch on? Are there too many channels, too many voices, too many angles and too many niches these days? Where in God’s name are we going?

You know who didn’t want to find out the answers to any of these questions? David Letterman, that’s who. Every Letterman junkie always knew he’d retire on a whim; that’s exactly what happened. No hype, no warning, no manufactured drama, nothing. Only Carson would have done it that way, and maybe that was the point. The old man told a story, then a second story, then a third story, and suddenly, he was gone. He’s leaving after his 33rd year. My favorite number. And now, officially, late-night television can morph into something else. I just don’t know what.

Filed Under: TV, David Letterman, CBS, NBC, Jay Leno, Late Night, Conan O'Brien, Jimmy Fallon, Jimmy Kimmel, Bill Simmons

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Bill Simmons is the editor-in-chief of Grantland and the author of the New York Times no. 1 best seller The Book of Basketball. For every Simmons column and podcast, click here.

Archive @ BillSimmons

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