Q&A with Jason Zinoman, Author of the New Letterman Biography

You’ve written a couple of books, but this was your first full-length biography. What reservations did you have about profiling Letterman, who can be a pretty elusive guy?
It took me awhile to even be comfortable with the term “biography.” My interest has always been in presenting a mix of reporting and criticism. I set parameters for myself: I would look at Letterman’s life, but only as it related to his work. But what I discovered as I got into the project was that talk show hosts are not actors. They’re not playing characters. Their lives are inextricably linked to their work. I had to make it biographical. As for reservations, I didn’t have many. I was excited to do this. I thought he would be a challenging subject because he can be elusive. But the best longform things I’ve done have always begun with questions I don’t know the answers to, mysteries I don’t understand. With Letterman, there were a lot of questions.
Had you interviewed Letterman before?
Never.
What was his reputation among the culture reporters and editors at the Times?
Oh, he has always been a critic’s darling. As an interview subject, though, he had a reputation for being a little prickly. And in the last decade and a half, he didn’t do many interviews at all—with the Times or anyone else. So when I started working on the book, I had no idea if he was even going to talk to me. I kept telling myself that was fine. And it made it a better book, because I reported around him like crazy. By the time he talked to me, I wasn’t on a fishing expedition.
What personal connection do you have to Letterman’s work over the years?
It’s not an overstatement to say he helped define my sense of humor, which is who I am to a certain degree. When I would tell a joke in middle school in the ’80s, I would swing my arm to the left the way he did. Of course, he did it to signal to the band for a rim shot. I had no band when I was walking around in seventh grade. But I’m not an unusual person in this regard. Among people my age, Letterman had a huge impact on the way people talk, their sense of irony. You even hear people like Tina Fey say this.
Which of Letterman’s comedic moments stand out over the years?
There are so many. The Velcro suit anticipated a lot of Jimmy Fallon’s stuff today. Taking the cameras to GE after that company bought NBC anticipated Michael Moore’s work and some segments on The Daily Show. The “Too Tired to Do a Show Show” where he just sat in his office in jeans the whole time was brilliant. And then there were moments that weren’t so important, but I just loved. He had this one bit about a giant doorknob. He kept explaining how big it was. There’s no joke there! But there was something about the absurdity of it.
What did you learn from your visit to Indiana for the chapters on his life here?
A ton. In some ways, that’s the key to understanding him. Here’s this moment in time marked by counter-culture tumult. On the surface, Letterman wasn’t part of that at all—he wasn’t a hippy, he wasn’t protesting the war. He was a member of a conservative fraternity at Ball State. But he led a kind of counter-cultural revolt at his college radio station that foreshadowed many of his battles at NBC. He kept making stuff up on the air, which infuriated the bosses there. What you learn from studying his time in Indiana is that he always had an instinct for irreverence. He couldn’t help himself. It was hardwired.
What kind of reception did Letterman give you when you requested an interview for the book?
Well, it took awhile to make it happen—probably a year and a half. But he never said no. And at many points, he could have been a hindrance and he never was. Every time I would call someone who was close to him and ask for an interview, the first thing they would do is call him and make sure it was okay. He never said, “Don’t talk to him.” Once the show had been off the air for eight or nine months, he agreed to meet with me. When he was on the air, his life was so crowded, the interview would have been different. The fact that he had some distance from retirement made it a fantastic chat. It was supposed to last an hour and it went on for four. He didn’t dodge any questions.
Can you share a few other details about that interview? Where did it take place? What was Letterman’s mood like?
It took place in a restaurant on 55th Street. We went at like 9 or 10 a.m., so no one was there when it began. By lunch, it was crowded. I’ve interviewed a lot of famous people in my career, but Letterman is different. Not only is he incredibly famous, but he’s remote enough that people freak out when they see him. I was trying to be locked in during the interview, but I could sense the tornado of fans around us. People were coming up to the table. Anyway, he seemed to enjoy the interview. That’s not because of me. He was a guy who for 30 years was the center of attention, then suddenly he didn’t have that anymore. I think there was an element of that he missed.
What do you make of his retirement beard?
Remember, he had a pretty bushy beard in college. If you go to Sigma Chi at Ball State, there’s a photo on the wall of his class. Everyone is clean cut in that photo except him. So it’s not the first time he has done this. And then his wife and kids didn’t like the beard when he regrew it, and that makes him want to keep it even more. People find it so strange and off-putting that it delights him.
What do you expect Letterman to do with himself going forward? Will he perform from time to time, or does he want to disappear?
I don’t think he wants to disappear. I would be surprised if he does another regular television show. But he admires Jerry Seinfeld, and Seinfeld could be a model. Here’s a guy who had tremendous success on television, then starts a web series [Comedians in Cars Getting Coffee] where he can create his own hours and not answer to anyone. Letterman may reappear in streaming format someday.
 
To read an excerpt of Letterman: The Last Giant of Late Night, click here.