May 20, 2015

My David Letterman Story

I’ve written before ( about how the beginning of my work career coincided with DL’s early network television days. At that time, I was working in the daytime programming department at 30 Rock, but got bumped up to primetime when my boss was axed. One of the great pleasures of working there was being able to watch live feeds from all the studios, and I spent altogether too much time looking at rehearsals for Saturday Night Live, Bryant Gumbel and Bob Costas’s NFL show, and my favorite, the morning David Letterman Show. Not since Steve Allen’s syndicated Westinghouse Show had I seen such an inventive, hilarious talk show. And sometime during the first year of his Late Night, David Letterman displaced my adolescent main squeeze, Soupy Sales, as my all-time favorite TV humorist.

Flash forward five years or so, and my writing career commences. I’m expected to make appearances on radio and television to promote my books. For some reason, while bookstore appearances made me nervous, I was happy doing media interviews, and as a student of popular culture, obsessed with both mediums, I was thrilled to meet and talk to most of my favorite broadcasters in both mediums. As a native Los Angeleno, I was thrilled to talk to my two radio idols, Michael Jackson and Bill Ballance, or to national figures like Regis Philbin, Tom Snyder, Joan Rivers, Martin Short, and Howard Cosell. Although I was on either Good Morning America or CBS Morning Show for every book, the Today Show eluded me. The Today Show was known for selling books. But the show I wanted to get on was David Letterman’s.

And then I got the call. I found out from a staff member of the show that executive producer Rob Burnett was a fan of my books. They were interested in booking me for the show, shortly before Letterman moved to CBS. I got a call from a segment producer and we talked about what Imponderables might work on the show, and less than a week later, I found out from my publicist at HarperCollins that I was booked. In no way was I thinking about this appearance as a career move. I know it sounds pathetic, but what I wanted more than anything was for DL to like me.

If I wasn’t worried about talking to DL, I did obsess about what to wear. I’m most comfortable in jeans and a t-shirt, but I knew Letterman preferred guests to dress up. So I did. I wore my best itchy Italian suit and instead of a conservative tie, I went with a pattern that I must have thought was “jaunty” at the time. The same segment producer met me more than an hour before the taping commenced, and I knew it was going to be a long haul, as authors are always on late in the show. We went over the Imponderables that Dave would be asking me about. I had never been asked to role-play like this before, and the producer stopped me many times and reiterated that I try not to be funny, that Dave liked authors to be authors and not be comedians. I knew exactly what he meant, as I had only watched David Letterman every night he had ever broadcast on NBC, but I pointed out that even done in a Tom Poston deadpan, some of the answers were inherently funny. But we hit an impasse. He implored: “Please don’t try to be funny.” I thought: “I know what I’m doing.” But I said: “OK.” I was fine when I walked into 30 Rock, feeling comfortable saying hi to some of the staff I knew from working on other NBC shows in the past. A cameraman I knew from soap operas remembered me and said: “Nice tie. That’ll look great on camera.” Jauntiness rules!

That night, Paul and the band were playing all Rolling Stones songs leading into and out of guest spots, and I remember standing in the wings waiting to go on while the band played a great cover of “You Can’t Always Get What You Want.” The segment producer had his hands on my shoulders and I’ll never forget the exact words he said: “Have fun, and please: Don’t try to be funny!”

Dave got up from his desk to greet me, and I remember only two things: he had an enormous head, and that he was the only host I can ever remember that not only gave me a firm handshake, but made genuine eye contact. He said to me something bland but welcoming, “Thanks for coming.”

But the first thing he said that the audience could hear was: “What’s the deal with the tie?” The audience laughed. I laughed, as I heard him say this more than once to a sartorial offender. Dave doesn’t do jaunty.

Dave started going off-script immediately. Most hosts are nervous themselves, and are concerned with the logistics of the work. They know when they are on-camera and when they are off-camera, and often give you nothing when there is a one-shot on the guest. Letterman was not like this. Even if he ignored most of the research, he was totally focused, and was generous. I was used to working with comedians, and especially enjoyed being interviewed by Joan Rivers (who I was not particularly a fan of as a comedian) -- her improv background made her listen intently to what a guest was saying, if only to score punchlines. But I loved being a straight man, and Letterman was gracious enough to feed me some straight lines, and to my eternal regret, the producer’s words echoed in my mind: “Please don’t try to be funny!” And to my eternal regret, I didn’t try, even though I knew Letterman wanted me to succeed. The segment went OK but was a little flat. I never watched it, even though I recorded it for posterity -- I knew I could have done better. I saw my tie in the monitor and I had to agree with Dave. It looked horrible.

But here’s the best part. As a viewer, I was obsessed with how Letterman treated his guests during commercial breaks, when he didn’t have to feign interest. I’m used to being ushered out before the next segment, but in this case, it was a musical act, so Dave told me to just stay in the chair. Letterman was in an exceedingly good mood (I am guessing that he had just made the deal to move to CBS to the 11:30 slot). As soon as the commercial started, he leaned over to me and said: “The colors in your tie are going to bleed together.” And then he told me that he enjoyed my appearances on Tom Snyder’s radio show, especially when we talked about broadcasting (as we always did after dispensing with the obligatory talk about my latest book). And then we talked some more about Snyder’s radio show. He was talking as a fan, and this just made me love Letterman more, if it was possible.

Despite any layers of irony, Letterman has always loved broadcasting. I have no doubt that his professions of affection for old-school performers like Regis Philbin, Tom Snyder, Bob & Ray, Howard Stern, etc., is heartfelt. I hope he can appreciate that his fans love him with a similar passion. For me, this is the hardest TV goodbye since the final episode of The Mary Tyler Moore Show. We may have never become buddies, but I’ll always cherish that commercial break with Dave.