“I’m regretting this already.” Not quite what you hope to hear at the beginning of an interview for your next book. I also heard, “I can’t imagine what this book will actually be” and “Is anyone really going to be interested in this?” Heck, I gave up trying to figure out what people were interested in years ago. That’s probably what made me a devoted Late Show With David Letterman fan to begin with. Dave fans tended to be on the outside, didn’t we? Dave never tried to please the home viewing audience at large. Why would I? I had been raised on David Letterman. As his long-time writer Bill Scheft put it: For a generation of people, Dave came with the television set. I was part of that generation.

I caught the Dave bug in the summer of 1987, between my junior and senior years of high school. I had regularly stayed up and watched Johnny Carson with my father on Friday nights, but he always turned the TV off when Johnny said goodnight and before Dave’s Late Night came on. When my father laughed at Johnny Carson, I laughed. Although I rarely got the references. (Who was Red Skelton, anyway?) That summer, I stayed up every night on my own, but I left the TV on when Johnny finished. Dave wasn’t Johnny at all. Dave was something completely different. He was something I got. When Dave said something, I laughed all on my own.

By the time Dave moved to CBS in 1993, I was a full-on fan. He had guided me through high school and college and had already shaped the way I spoke, the way I told a story, and the music I listened to. I am pretty sure I watched every installment of the Late Show on CBS from 1993-2015. I don’t have the paperwork on that, but I don’t ever remember missing a show. Watching Dave was part of my daily routine. Dave got me through my first marriage. He was there when I was a stay-at-home dad of twins. That was when I started taping the show and watching it the following morning. When I started traveling on a weekly basis, I would listen to the VHS tapes in the minivan’s VCR. I watched through marriage and divorce, in my parents’ house, my own house, back to my parents’ house, and on to another marriage. When I got my corporate job, I streamed Dave every morning through the internet, pretending to be answering emails but really listening to Top Tens and great interviews and dancing in my swivel chair to music by Paul Shaffer and the CBS Orchestra.

In 2015, I recorded Dave on my DVR, because it was free with my job at a cable company. It was on that DVR that I decided to keep the final six weeks of the Late Show. “Decided” is a strong word. I just couldn’t bring myself to actually hit that delete button. The final weeks of the Late Show stayed there for two years, taking up valuable family hard-drive space. (“Dad, can I delete these Late Show episodes to tape Teen Wolf?” NO.) That is when my job was downsized. 

“Downsized” is a word that corporate stooges made up. The kind of stooges that Dave would try to deliver a fruit basket to and then be thrown out. I wasn’t downsized; I was fired. When your place of employment asks you to not come back, you’re fired. I didn’t care. I was ready to go off into the world and become a writer anyway. There was only one part of being let go that hurt—I had to turn my DVR back in. That meant giving up Dave for good. I looked at the calendar. I had just about twenty-eight workdays left. Dave had been there for me through all my changes in life, why not through this one as well? I would rewatch one episode a day. Dave was losing his job; I was losing mine. We would get fired/retired together. 

I hadn’t watched late-night television since Dave said “Thank you and goodnight” to all of us on May 20, 2015. After twenty-eight years of watching him, I didn’t see much point in trying someone new. I also hadn’t watched a moment of Letterman since he left the air. No, I had kicked the late-night habit cold canned ham . . . I mean cold turkey. But it was now or never. The equipment was going back whether I watched the episodes or not. I started my rewatch of the Late Show almost two years after it ended. I went right back down the rabbit hole. I watched these magnificent hours with a fresh perspective. The country was completely different now. The world had been turned upside down. Every part of pop culture had been radically changed by the events of 2016. Everything, that is, but the six weeks of the Late Show episodes that had been frozen in time on my DVR.

Conversation, dignity, class, and even comedy had all drastically changed. The world had become less civil; face-to-face conversation was almost nonexistent. Dave and his guests actually talked to each other. Very few of the guests were appearing on the show to promote their latest movies. They were coming on the show to talk to their friend. The few guests who actually did appear only to promote a movie stuck out like a sore thumb. Somehow the producers and staff of the Late Show had broken the late-night mold again. This time they brought it back to the days of Jack Paar and Johnny Carson. For six weeks of time, conversation was the true king of late night. Sitting there, watching these mesmerizing television moments again, I got an idea. As Dave always said, “There is no ‘off’ position on the genius switch.”

I would document the last six weeks of David Letterman’s time as the longest-running late-night talk show host, 1982-2015. My plan was to skip the first thirty-two years and forty-six weeks (what could possibly have happened during that time anyway?) and look only at the end. I would conduct interviews with the people who had crafted what may very well be the end of television as I knew it. Television wasn’t even televised any more, it was streamed. Any star who came after Dave would be an internet or YouTube sensation. David Letterman was a broadcaster, and the last of his kind. I set out to capture the moments of those episodes and color them with comments from writers, directors, producers, and crew. If things had changed that much in the world in less than two years, how much would things change ten or twenty years from now? How much would be totally forgotten? Now was the time.

As I started interviewing the Late Show staff, I discovered that just about everyone thought this idea was a little nuts. They were skeptical that the show still mattered. They doubted anyone would care, or even remember what they had done. Every time someone on the staff said that, it only inspired me more. Not because I wanted to prove them wrong, but because their reaction was so Dave. They had his sensibility and predilection for self-deprecation. How could they not? They had spent years trying to write and create a world where Letterman was the centerpiece. Dave never understood why he mattered so much to us. Every time a guest tried to explain how much he meant to them, he dodged and ducked. I imagine he would think it was crazy that I watched him faithfully for well over half my life. From job to job, from state to state, in the car, at work, on vacation, through an antenna, a cable wire, a computer screen, and, inconceivably, on a telephone. There was no way I was the only one. 

This book will cover those final twenty-eight shows, from Sarah Jessica Parker on April 3, 2015, Dave’s 6,000th show, all the way to the Foo Fighters on May 20, 2015, Dave’s 6,028th installment. That is correct, I am ignoring the first 6,000 hours. So Joaquin Phoenix, Drew Barrymore, Madonna, and late-night wars are not rehashed in this book (not counting my coverage of the special that CBS aired during those final weeks about Dave’s career). The hope is that by focusing the lens tightly on twenty-eight specific episodes, this book will reflect the artistry of past episodes as well. 

I was fortunate to get the enthusiastic (and sometimes reluctant) participation of over twenty people who worked at the Late Show, which allowed this book to become a detailed look at what they had accomplished. Everyone was extremely generous with their memories, time, and photos. But, I would be remiss if I didn’t single out executive producer Barbara Gaines. She was my first interview and a true champion of the book. She said she wanted to help because those six weeks were the highlight of her professional career. I strongly agree. I think it was the highlight of all involved. The staff’s dedication in supporting Dave’s farewell is something that television history needs to be mindful of. 

What you will learn from reading their combined interviews, which are dispersed among recapitulations of the twenty-eight episodes, is that the Late Show staff was a family. They were loyal, not just to Dave but to each other. Some of them worked there for a decade or two, or, in Barbara’s case, three and a half decades. That is loyalty. That is family. That is also unheard of in the television industry. And while I never did get an interview with Dave for this book, I know that if I had, he would have had just one thing to say: “I’m regretting this already.”