David Letterman Showed Me How Comedy Could Be Subversive

First off, in a crowded landscape of David Letterman tribute pieces, I want to thank you for choosing to click on this one. I will try to do justice to Letterman’s immeasurable contribution to television comedy in the best way I know how: by making it about me.

I met David Letterman once. When I was 16 years old, I had my own late-night talk show on MTV. You can look it up if you want. It was “cool,” and “incredibly groundbreaking.” The Beastie Boys were “huge fans of it” and then it got “cancelled” when I was 17.

The day I got the bad news was the day I met Dave. It was the summer of 1996. I saw him walking on the corner of 53rd and Broadway, making his way from the Hello Deli back into the Ed Sullivan Theatre.

I had to say something. I couldn’t stop myself. I remember at that moment feeling like I had no idea if I was ever going to be in show business again. It seems laughable now as I write this from my fancy Hollywood office (I am very successful), but at 17 I figured, “When am I ever going to get the chance to talk with David Letterman?” So with all the hubris only being a teenager can bring, I went up to him.

“Dave, I had my own talk show, but they just cancelled it. What do I do?”

Without stopping, as he continued his brisk walk back into the studio, Dave said to me in the most perfect I-am-not-happy-with-my-life Letterman deadpan:

“Do you want mine?”

And then he was gone. Dave breezed back into his insanely over air-conditioned studio, and I ended up at the Upright Citizens Brigade Theatre. We both had another 20 years of struggle ahead of us.

I have no concept of comedy without David Letterman. I was four years old when Late Night premiered on NBC. My introduction was a VHS tape in my Dad’s house of the 1985 David Letterman Holiday Film Festival, which included the Merrill Markoe–directed video for Dress Cool starring Paul Shaffer and the World’s Most Dangerous Band.

Watching Late Night with David Letterman felt dangerous. Try to imagine you’re a small child and all at once, you are flooded through your entire body with a complete understanding of what it means to be subversive. I don’t know what holds that kind of power today for young impressionable children who will sadly grow up to be comedy writers. For me, it was unquestionably Dave. He was the first guy I saw on television and said, “Oh, if I can somehow convince them to give me the camera, I bet I could get away with something.”

Cher was right: Dave was an asshole. God, do I mean that with the greatest of affection. Think about the television landscape in 1985 when I first started watching Late Night. Sure, there was Cheers, but there was also a lot of Silver Spoons and Punky Brewster. I liked those shows too (I was six), but I knew even then, the real stuff, the stuff the grownups liked… that was happening in the middle of the night. We needed an asshole like Dave to say, “Alright, now that the kids are asleep, let’s bring out Sandra Bernhard and Madonna. Oh, and by the way, they’re probably fucking.”

We needed “Hal Gurnee’s Network Time Killers,” a bit that said, “Look, it’s 12:30. We’re trying to fill an hour here. This whole television thing is stupid to begin with, right? What, you’re looking for some entertainment? How about a Kenny Rogers impersonator? Does that land? No? Whatever. We just killed two minutes. Let’s bring out Bryant Gumbel.”

No one worked harder at putting together a show that looked like it was on the verge of falling apart at any moment more than the writers at Late Night with David Letterman. It was controlled chaos. I mean, look, they put this on TV:

They actually put that on TV more than once. Bananas.

I was the one kid at school who watched Late Night with David Letterman. As I’ve gone through life, I’ve been lucky to connect with the other people who were also the one kid at school who watched it. I hate to think how depressing it would be if we all didn’t find each other.

When NBC passed Dave over for The Tonight Show I took it personally. Those weasels at GE didn’t pick my guy. Leno was fine, he made me laugh, I wasn’t offended by him telling me, “Crunch all you want, we’ll make more.” Leno has been turned into some kind of comedy supervillain, but in 1993, he just wasn’t my guy. I liked Dave. I still like Dave.

So when Dave jumped ship to CBS, I was there opening night. I knew things were going to be just fine the minute Paul Newman asked one simple question:

“Where the hell are the singing cats?”

The show was a little bigger, but not that much. Dave was still Dave. And what strikes me is that he has remained utterly Dave on CBS for the past 22 years. I can’t think of a single moment in my entire life where I turned on Letterman and thought, Wow, he’s really pandering tonight. You never sensed a moment of desperation coming off him. This was broadcasting at its finest. He made us feel like he didn’t care when of course, no one cared more. Night after night, he blended high status with self-deprecation.

He knew when to let Howard take over. He knew exactly how to make fun of Regis. He knew when to feign outrage at Madonna. He said what we needed to hear in the days after 9/11.

Dave cheated on his wife. He cheated on his wife and he got caught. Then he sort of forgot to apologize for it. People didn’t like that. Like I said, Cher was right.

Related: The Real Kenny Powers?

I wonder sometimes if late-night network television can break the rules anymore. The truth is, Dave already broke them all. He smashed the genre into a million pieces. It’s gonna take a while to put things back together. Not to say the guys with the job now (and yes they’re all guys, we should fix that) can’t do great stuff. They can and they do. Every night.

But there will never be anything like Dave.

We don’t consume late-night television the way we used to. We see it the next day, in clips online. I don’t know if that’s a good or bad thing, it’s just new. David Letterman is retiring in a very different media landscape then the one he started in. And I have absolutely no doubt that if he chose to stay on the air longer he would’ve navigated that landscape brilliantly. The final years of his show are all the proof you need. Has Dave ever felt irrelevant? Not for a second.

I am incredibly lucky to be one of the writers for Billy on the Street. As we were working on the fourth season this year, Billy came in to tell us that Letterman had agreed to leave the studio and go out on the street with Billy. This is something he hadn’t done in years. We were thrilled. We immediately started brainstorming with Billy on how we could take to the streets and ask people, “What the hell is Dave gonna do now?”

I can’t tell you what it meant to me to be involved with something that aired on Letterman’s show. I called my Mom. Nineteen years earlier I was pestering Dave on the street. Now he was on the street with Billy doing the pestering.

Follow Jake Fogelnest on Twitter.