Author Scott Ryan discusses his new book: The Last Days of Letterman

David Letterman behind his desk

For 33 years, David Letterman has been making audiences laugh with his irreverent  sense of humor and lunacy. In May, 2015, after 6000 episodes, more than twice as many guests, several hundred cans of SPAM given away, 150 Regis appearances, some of the most memorable (and contentious) celebrity interviews (Madonna, Joaquin, Farrah) of our time and one highly publicized network switch, David Letterman ended the show which meant so much to many fans.

One of those fans is Scott Ryan (author of the book Thirtysomething at Thirty: An Oral History and Managing Editor of the Blue Rose Magazine). Because Letterman meant so much to Ryan, he interviewed many production individuals who put together Dave’s final 28 shows. They are collected in The Last Days of Letterman—The Final 6 Weeks, Ryan’s new book which will be available in early November.

It was a great pleasure to interview Scott about his book seeing as how I am also one of the die-hard Letterman disciples his book is written for. It was wonderful talking with Scott and I’m very glad our conversation went much better than one of Alan Kalter’s celebrity interviews.

Jason Sheppard: When did your love for David Letterman begin?

Scott Ryan: Well, it’s hard to pinpoint a moment because he’s sort of been in all our lives forever, but It was really the summer of sophomore and junior years of high school that I started to stay up and watch Late Night when he was on NBC at 12:30. I would watch Johnny Carson with my dad on Friday night but I didn’t really get it. I loved Johnny but I was just too young—watching him was just something I shared with my dad. But Dave, through that summer, with his brand of humor was speaking to me through his irreverence and disregard for establishment. As an older teen male I just became obsessed with Dave and I’ve watched him, really since then. I start this book by tracking my life with Dave in a chapter that I called, “My Monologue” which I wanted to set up to let the reader know why the show ending mattered so much to me. You know, it’s not like every episode that Dave did was the greatest but it became this constant in my life that you knew Dave was going to make you laugh. And it’s as simple as that. There’s nothing more complex—you just knew that you were going to sit down and you were going to laugh and what a gift that was to give people.

JS: Why did you choose to write about the last six weeks rather than the last year or last six months?

SR: Part of it is because it’s what I had. I could not bring myself to delete the last six weeks off the DVR. I actually would watch Dave in the morning throughout the last couple years and when I would watch an episode, I would delete it but when it got to the last week before the final six weeks, I kept them. It made more sense when I wrote the book to write about the last six weeks because between the seventh and sixth last weeks, they took a week off so to cover the last six, there was something numerical about that. The last seven weeks just didn’t sound as good (laughs). It was actually the Friday before the last six weeks when they had on Mike Myers and to me that really was the beginning of the end. Mike did a really great tribute to Dave and I hated to leave him out of the book and I tried to think of ways to cheat and get it in but then they had the next week off and came back with Sarah Jessica Parker and that’s when the ball really started to roll. Also, I didn’t want to do the last year because I wanted to take a micro-look at the episodes. I didn’t want to take a big look at Letterman—I wanted to really dig down and show how these episodes mattered.

Sarah Jessica Parker kicks off David Letterman’s final six weeks in April, 2015

JS: How did you convince staffers to speak with you?

SR: (Laughs) Believe me…it wasn’t easy. Honestly, when I saw the montage that executive producer Barbara Gaines had cut—the one that had thousands of clips in it to be shown during that final Foo Fighters performance live, I contacted her. I used to be a video editor so I knew how hard that was to do. It just totally fascinated me that somebody could do something like this and I started to contact her then over Twitter in May, 2015 and I got my interview with her in August, 2017. It took two years to get my first interview. I just kept tweeting her for those two years and the funny thing that was driving me crazy was that she would like my tweets (laughs). I would say ‘Barbara, I would really like to interview you about your montage’ and she would like it and then I was like ‘what does that mean?‘ And eventually she said ‘okay’ but then that took another 3–4 months. Finally, one day she sent an email and said ‘do you still want to talk to me?’ That was in August of last year and then I did 20 interviews. Once I got Barbara Gaines then everyone was willing to talk to me because I started at the top.

JS: Do you think she needed to put some time and distance in between actually opening up about her time with the show?

SR: Oh, definitely. Had I got the interview with her in 2015, I don’t think it would have led to the book. She would have had a totally different opinion and I wasn’t even contacting her for a book—I just wanted to get her on my podcast (The Red Room Podcast) where we cover television and all kinds of different things and interview her about how the heck she made that video that blew my mind.

Executive Producer Barbara Gaines looks out at the Ed Sullivan theater while preparing that day’s show

JS: There have been a number of books about David Letterman published in the past including Bill Carter’s The Late Shift. A lot of these books have portrayed Letterman in a bit of a negative light. Is this something you chose to avoid?

SR: There’s a two-fold answer to that—I have no interest in anything negative in life, which makes me possibly the worst television historian and author that there ever was (laughs). If somebody would have wanted to talk negative, I’m just not interested in it, and that doesn’t mean I’m not interested in the truth but this book is about craft. I wrote another book about Thirtysomething and it was the same thing. I mean, who cares if you liked someone you worked with or not? I’m not really interested in that—I’m interested in ‘how did you create this piece of art?’ I wasn’t digging for any dirt, I was digging for ‘what was your day like?,’ ‘what were your activities?’ and that’s what they gave me. So I never asked anyone if they liked Dave or if Dave was nice. Those were not questions I would have asked anyone. Now on the flip side, you hear in the answers what they gave. Because I never asked about Dave, they told me how they felt about him and you get it from them because I’m not pushing them to go that way. The other thing is this book isn’t told in my words, it’s told in theirs. I just wonder how honest those other books were. In fact, some of the people I’ve interviewed even said that in other Letterman books, they’ve been misquoted and made to seem more angry with Dave. These people love Dave. I don’t know if this book will be reviewed but I wouldn’t be surprised if someone said ‘oh, well, Scott Ryan is just a fan so he’s just giving a fan view’. That’s not really true. What I was asking them was about those episodes and then they told me. It’s not like I cut nasty comments that they said—this is what they said.

JS: That Barbara has been working with Dave since 1980 is a testament to the kind of loyalty Dave earns from his co-workers. Did you want to interview people who have had a long history with Dave?

SR: From a critical standpoint of view, I only interviewed people who were there for the last six weeks. Maria Pope, who was an executive producer for many, many years, left before those last six weeks to work on The Tonight Show and people asked me if I wanted to speak with her and I said, ‘no. She wasn’t in the last six weeks and that’s all I’m covering’ so, I didn’t talk to anyone who left. I’m sure Maria wouldn’t have said bad things but I didn’t talk to anyone who left the show or was fired. I was talking to people who were willing to go down with the ship. That’s why I think it’s all positive.

Martin Short serenades David Letterman one final time on May 6, 2015

JS: Do you have a personal favorite episode or moment of those last 28 episodes?

SR: For me there was a personal moment and that was definitely the Martin Short/Norah Jones episode. This is where my editor and I kind of went around and around (laughs). We kind of had more trouble with that episode than anything else because that is the episode where I truly grieved losing my TV friend. First of all I love Martin Short, he was always a great guest. Just watching Dave and Martin was so much fun and then you follow that up with Norah Jones singing “Don’t Know Why” which she debuted on The Late Show in 2002. Well now I own every Norah Jones record because she’s one of my favorite singers. I discovered her because Dave put her on TV. It was listening to her sing that I realized that I wasn’t just going to lose Dave, I was also going to lose the greatest Spotify mix-list ever! This was where I got so much of my music from and with Martin Short, so much of my comic and storytelling and it was that show that I really realized that I wasn’t just going to miss fun time with Dave. I was going to miss all the ways that he had changed my life in positive ways. So it was hard for me to write about that episode and my editor kept saying ‘cut that – nobody cares about that’ and this was one of the times where I sort of did exert myself into the book because that episode meant so much to me and I feel that everybody probably has a different moment and when I interviewed people, I would ask them ‘what was your Norah Jones moment’ when you really realized what you were losing.

JS: I believe my ‘Norah Jones moment’ was the Tom Waits performance during the last week where he performed “Take One Last Look”—a song he had written specifically for Dave.

SR: If I have one regret for the book, it’s that I couldn’t get permission to print the lyrics to that Tom Waits song. I wanted to so badly because that song is not available anywhere. He just performed it that one night and I really tried. I went to Tom’s website, I got his agent, I tried to go through the Letterman people and I just couldn’t get through to Tom Waits. I don’t think he would have minded but obviously in this day and age you can’t take that risk. Those lyrics are perfect and I do tell people in the book to go onto YouTube and watch the performance because they are really beautiful lyrics. But I really wanted to print them so bad.

David Letterman and Julia Roberts have been bantering (and flirting) with each other since 1989. Her Final appearance (and kiss) was on May 14, 2015

JS: Was there anyone you wished you’d spoken to for your book that you didn’t get to include?

SR: Yeah, there were those. I really wanted to talk to Jude Brennan. I tried very hard but she just didn’t want to. Often, when I would talk to someone they would ask, ‘did you get Jude?’ and I’d say, ‘no, I never got her’ and then they’d say, ‘yeah. Jude would never talk to you’ (laughs). I really wanted to get Nancy Augustini who produced the show on the floor with Barbara Gaines for the last six weeks. I wanted to get to her and she declined. That was a perspective I really would have enjoyed getting. I really wanted to get Todd the cue card boy and I just could never get through. I think they would have added something nice to the book. I’m kind of okay that I didn’t get people like Paul Schaffer or Alan Kalter or Biff Henderson because they were all such iconic on-screen people and this is more about the backstage people than the onstage people.

JS: Scott, Do you still watch late night TV?

SR: I tried to watch Colbert because I loved Stephen Colbert when he was on Comedy Central but I couldn’t do it. I just couldn’t watch it. It was like being in the same studio but it wasn’t Dave and I just wasn’t ready so I didn’t watch any light night TV for probably two years. But recently, I have started watching Seth Myers because I love his “Closer Look” so I’m kind of back in the game but I did take that time off. I didn’t even watch any Dave until I started the book so I didn’t watch any Dave from May 2015 until August 2017. I thought I would always watch his Christmas show but I couldn’t even watch that. I’d given it up.

JS: That’s one thing I miss as well. The Darlene Love performance around every 21st of December and when that time comes around each year, realizing that we’re not getting that anymore—to me it feels like this emptiness.

SR: Oh, yeah and Jay Thomas’s Lone Ranger story and the meatball on top of the Christmas tree—I want it all. I want the Cher story from Paul. I want it all (laughs). Now I do have two versions of the Christmas shows—I have the 2012 version and I did keep the 2014 one. I do have them but I haven’t watched them.

The final Top Ten list read by long-time friends of the Late Show with David Letterman

JS: Was there anything written for the book and left out?

SR: No, not really. The book is pretty much it. There won’t be a bunch of deleted things from the book. We need to remember that you don’t have to tear everything down and there’s nothing wrong with paying tribute to something and that’s what this book is—it’s a tribute. The only thing is that this will probably be the pinnacle of my life so I’d better really enjoy it (laughs). I don’t know if I will rise to such a height again but I’m trying to enjoy every moment.

The Last Days of Letterman by Scott Ryan

The Last Days of Letterman—The Final 6 Weeks by Scott Ryan is available in bookstores Nov. 6 and can be purchased online at Fayetville Mafia Press (Use the coupon code 25YL to get $4 off!)

Written by Jason Sheppard

Entertainment reporter living at the end of very cold Canada. Proud owner of a diploma in journalism and just about every CD by John Williams ever released. Favorite directors are Spielberg, Scorsese, Kubrick, Tarantino, Fellini, Lynch and Fincher. Twin Peaks, Sopranos and Six Feet Under are the greatest TV dramas ever crafted and I love 90s sitcoms such as Spin City, Sports Night, Newsradio, Seinfeld and even that one with Deadpool working in the pizza place. Click linkies below to follow me.

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