The David Letterman Legacy: Saying Goodbye Is the Hardest Part

There's nothing left for the modern architect of the late night landscape but the farewell.
Evan Agostini/Invision/AP

I've written about David Letterman so many times that now they all seem to blur together, but none of the previous times were laden with the kind of sadness I feel this time. No getting around it, really — there’s a lot of melancholy in the room as Wednesday arrives.

I’ve watched these Letterman farewell episodes and done plenty of tearing up in the process. And I've marveled not only at his legacy and endurance and influence (all the obvious things we talk about when someone like Letterman retires), but also simply how much people really do love him and will miss him.

If you’ve lived long enough and watched enough television you’ve seen plenty of farewells. If there’s anything notable about the departure of a true ground breaker, it’s the legitimate appreciation on hand. You can’t fake some of the tears and the looks these celebrity guests and friends have given him. With the whole late night talk show circuit built on phoniness — which Letterman spent a career tearing down — it’s especially gratifying to see real, unfettered appreciation and respect.

Even if it makes you sad.

I watched Letterman in high school and college and then covered him professionally for years. So I've often felt a strange kind of intertwined existence that's made everything seem personal with Letterman. When I was just starting out as a TV critic, working at a mid-sized suburban newspaper, it often felt like writing in a vacuum. I had no idea if anything I was doing was making much of an impact in the greater world outside. Then Letterman sent me a letter, thanking me for a column I wrote about how people seemed to be forgetting him, looking for the next new thing.

“Completely and utterly unexpected” can't begin to explain what it was like getting that letter. God or Santa Claus could have sent it and I’d have been less surprised. Letterman’s notorious private persona at the time made the letter all the more special and shocking. Maybe it was the Midwesterner in him, but I thought it said a lot about both his generosity and sincerity to send it.

It was the first of two letters I got from him. The second came when I was a TV critic in San Francisco with a much bigger audience, but the sentiment I felt when I received it was the same. I saved both.

From there, I saw him when he brought the show to San Francisco, and went to a taping in New York. I continued to watch The Late Show regularly, recording episodes when I couldn't watch them live.

Like everybody else praising him as the end arrives, looking back at clips from the very early days of the ‘80s reminds you of not only how much he's evolved as a performer, but also of the very singular spark that's always been there. You begin to see him morph from outlandish, hilarious behavior to a slightly more reserved, more statesman-era host at the top of his game, interviewing and doing bits on the street, taped elements, etc. — all the stuff, in other words, that everybody else in the late night game would either steal or aspire to. He'd invented the formulas and set the bar for them. Letterman was how you did it. Letterman was who you’d want to emulate if you were in the game (and his fellow competitors would later acknowledge that).

And then there was his further evolution toward a wise, patriarchal presence. He showed some vulnerability, sharing personal stuff a little easier. There was the heart surgery. Then there was 9/11, after which he was the first host back on the air, getting right to the core emotion of all of it from his stage in the middle of a grieving New York City. There was, of course, the scandals of his messy personal life. Then he stopped trying to pretend about his rivalry with Jay Leno, which opened him up further to his audience. He grew into a true statesman, going from being prickly and uncomfortable talking about personal matters and authentic sentiments to someone who could give the most sincere compliment, the most heartfelt speech.

It was rewarding to watch, sure, but I’m not sure Letterman ever wanted to be the elder statesman of the late night crowd. It’s just such a grueling job, and doing it for 33 years really is some form of insanity.

When Letterman announced his retirement, I wrote a story about it, noting there were nights I’d tune in and he seemed, well, slightly bored by it all. And I totally understood why he would be. At some point, it ceases to be fresh or interesting unless you’re still highly motivated to make it so. Certain guests — both actors and musicians — would bring that interest back; you could feel it happening. And it never got old to see Dave crack himself up or just find the most random thing enjoyable. Those were always great moments. But somewhere in the recent years, you could see he was thinking about the exit.

The thing is, all the magic that Letterman brought to late night is now evident all over the place. And that’s a real positive. The late night landscape is in great shape — Jimmy Kimmel, Conan O'BrienJimmy Fallon, James Corden, Seth Meyers — and of course Jon Stewart and John Oliver. When Letterman leaves, one of the most creative people on the planet, Stephen Colbert, will replace him. We are not lacking for entertainment, for depth, in the late night arena.

So when Letterman announced his retirement, it seemed like a fitting time. It was on his terms. It was to be the end of an era — a direct link back through the one and only Johnny Carson, the man who loved Letterman and who, in turn, Letterman shared jokes with after Carson was long gone.

It’s a bit of a younger person’s game these days. Letterman is the Carson of his generation. He’s the departing giant, the retiring legend. I thought he was probably happy to move on back when he announced it. But, not completely unexpectedly, you can see that fire in his eyes during this victory lap of sorts. That joy. The last month or so in particular, you can see the rejuvenation, the laughter. You can also see how he’s taking it all in each night. How much it all means to him. How he appreciates the people paying their respects and wanting to have one last good time with him, one last appearance.

Who out there wouldn’t want that? I’ve never met the man but I’m going to be wrecked by watching his departure.

The legacy is written, and his tenure is the modern canon. Letterman essentially came into the late night world, tore it down and rebuilt it in the image we see on every channel, in the work of every host out there. There’s a hell of a lot of glory in that. What a fantastic, memorable career — so comprehensive that there's nothing really left for him to do in it, except say goodbye.

Twitter: @BastardMachine