Keith Olbermann: A Letterman Appreciation – You Know Him, You Love Him, You Can’t Live Without Him

My perspective on David Letterman is a little different, I think, than most of his other frequent-but-really-not-that-big-a-deal guests. For one thing, while I can still be freshly awestruck by his intelligence and his creative genius, I like his humanity even more. The thing I like most about Dave is Dave.

Plus, I had been a fan for 25 years before I was ever on the show, and I had managed to meet him at NBC even though neither of us worked there. I was just leaving 30 Rock to get back to ESPN when I heard this very familiar voice shout my name and then, “What the hell are you doing here?” I explained, with a mixture of surprise and pride, that Bryant Gumbel had brought me down from Connecticut to be the sports guy on a panel for the Today show year in review for 1994. Without missing a beat David said, “Well I don’t believe that for a minute,” and then he excused himself to pre-tape something with Bryant. “I gotta go make an ass out of myself now.” It was about 9:30 in the morning, and it was a great practical demonstration of how hard this man worked to make that show what it was.

The process of making that show was not like that with Jay Leno or Craig Ferguson. Craig would have said hello to you three times and hugged you twice by the time you came out onstage, which was warm and lovely. Jay would come in to your dressing room and sit on the couch and talk to you for half an hour, which was also very generous (and entertaining; a producer once literally pulled him out of my room). These were gregarious guys, and Dave wasn’t. I never saw him at CBS except when we were on the air. When I started going on in 2006, for all I knew he was actually built into the desk like Captain Pike from the Star Trek pilot and they threw a tarp over him after the show was over.

But then, for whatever reason, he let me “in.” Even counting every time I was on — and I did one silent cameo and another bit where I broke into the studio, and best of all, I once got to do an entire Top 10 list — I don’t think I made the list of the top 100 most frequent guests. Maybe I was on 16, 17 times. But after I’d been on once or twice, David started to talk to me, very confidentially, especially during the commercial breaks on those nights when I was on for two segments. I mean, we talked about my dad when he was in the hospital, and we talked about his mom, and we talked about our respective cases of shingles — all the stuff Dave supposedly never talks to anybody about.

And one night he leaned in over the band and shouted, “Punch me in the throat. Hard, OK?” and went on to explain how somebody somewhere was making waves about something on the show. I don’t know why I was so overwhelmingly moved by this — maybe it was that he was confiding in me, or maybe it was just that here was television’s Babe Ruth being yelled at for inconveniencing the neighbors by losing all those baseballs when he hit home runs. So when I got home, I wrote him a note explaining that from my point of view as a fan and as a political commentator, he had taken a goofy comedy show and grown it into one of the last outposts of edgy, sincere, fair political and social satire and criticism and that he should never see it as anything less than vital and necessary. And a week later I get this letter from him in the mail. And it’s basically six or seven different versions of the sentence, “I can’t tell you how much your note meant to me.” I cherish that letter. I’ve never so much as had a meal with him, but I would go through a wall for that man.

I’ve never so much as had a meal with him, but I would go through a wall for that man.

Professionally, I’d follow him through a wall. Every time I’ve watched, every time I’ve been on, I’ve been amazed at just how great a broadcaster he is. My only real skill is versatility. But David is versatile in ways everybody else in the medium lumped together couldn’t manage. From the monologue to the taped bits to the Top 10 lists to the animals to the fluffy kids interviews to being the straight man for a thousand comedians to the post-9/11 show to the serious interviews — and he might be the best political interviewer of the last 20 years — to the day he got laughs while confessing to and cleaning up his own potential scandal, if you wanted to replicate that show you’d need half a dozen hosts all onstage at once. He’s doing that many different jobs with different skill sets, all at once.

One night those skill sets combined to produce the highlight of my career. I’ve done a lot of stuff in 35 years in this business. I’ve anchored everything from a presidential primary debate to the World Series. Just in Dave’s realm, I’ve been on the shows of nine different late-night network talk-show hosts. But the night John McCain bailed on him in September 2008 tops it all. David and his staff had about 15 minutes to find somebody else, and they called me. I’m not kidding myself here: I was a) in an office five blocks from his studio, b) free for the next hour, c) a political guy when they had just lost their only guest who happened to be the GOP nominee for President, and d) I had already once come in as a pinch-hitter for a same-day guest cancellation. But to turn to me? I would have cancelled the show before I had me on!

Instead, I got to be a witness to history on two levels. First, obviously: That was the last day McCain had a real chance to get elected. Lying unnecessarily and stupidly about suspending your campaign to a guy with a nightly network talk show and a brain that can go a thousand miles an hour? Finis. And I got to watch Dave hammer in the final nails that the senator had so thoughtfully provided, and then I got to go back and report on it on my own show as breaking news!

But just as amazing was to watch David Letterman’s mind work, up close, in real time. When he started the show he fully believed McCain had told him the truth: that he was rushing back to Washington because the economy had “cratered.” David wasn’t happy about it, but he accepted it, and he kept his humor low-level and very specific — just variations on “Wait. You can’t do a talk show and deal with the economy?” — and he wasn’t even going to leave McCain black and blue, let alone wounded. Then he brought me out, and I said I thought it was a significant moment in the campaign and he continued to get huge laughs with variations on that one joke, but as he did, he also interwove questions about the political implications intelligently and expansively.

John McCain David LettermanAnd then during the commercial break after my first segment, somebody — I think it was Barbara Gaines — exploded onto the stage with the news that McCain hadn’t gone to Washington, that he’d merely gone up the street to do an interview with Katie Couric on the CBS Evening News, which they were taping while we were taping. And they rolled out a monitor, and there he was. And David looked at me and his eyes narrowed and I think what he asked was, “Am I assessing this correctly?” and I just nodded in agreement. And Dave had maybe 30 seconds before the break ended. And what he then did extemporaneously could not have been better had they spent a week trying to script it.

He conveyed the new facts as solidly as any newscaster. McCain actually had ditched him. This meant that a man who wanted to be President hadn’t been smart enough not to lie to him about going to do another show on the same network. It also meant it hadn’t dawned on him or any of his advisers that Dave could watch that other show on an in-house feed. And that’s when he started shouting questions at the monitor showing the McCain-Couric interview. And then the startled humor of “can you believe this is happening now?” turned into poison blowpipe darts. Keith Olbermann David Letterman 4And because he had been grudgingly understanding during the monologue, the audience — the country — gave him every right to shoot them, again and again and again. Two or three basic joke premises, and each time he twisted them just slightly and got a bigger laugh — for the rest of the show. For the rest of the campaign, as it turned out! And I got to sit there and watch Creative Genius in Progress, while I happily turned into Ed McMahon (“You are correct, sir!”), because my contributions were unnecessary except to the extent that they let Dave clear his throat and collect his thoughts for 10 seconds at a stretch. It was as impressive a bit of broadcasting as I’ve ever seen on the air, never mind in person. Plus it really was a moment in American history. And I had the best seat in America for it.

So I’m a fan on all levels, and on the human one, I’d like to be as decent a man as Dave, if-or-when I grow up. Which leaves me with only one complaint: that after May 20th he’s not doing the show any more. It really is like watching Babe Ruth quit.

Of all the people on television — this man is retiring? He should be on the air even after they really do have to make him Half-Hologram. Or like that Star Trek captain, solder him to the desk.

I know I’d still watch.

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