Why David Letterman Matters (to me)

Next Wednesday, May 20th, the talk show host David Letterman will retire after serving 33 years behind the desk in late night. It’s an accomplishment unparalleled in television, unlikely to be repeated.

In this hyperconnected social media world, the late night talk show doesn’t really make much sense any more. Why is this on at 11:30? Why not catch up with (the insufferably earnest, if you ask me) Jimmy Fallon when you hear about his latest lip synch sensation on Facebook?

But if you only know Letterman for his show in recent years, then you won’t understand why this occasion means so much to people like me. Back in the days salad days of Network Television, there just weren’t that many places to find odd, cynical voices on TV .

There were four networks and there were two or three late night shows on TV. (In my early teenage years these were Johnny Carson, David Letterman and Arsenio Hall). That was it at late night: M*A*S*H reruns or a talk show.

I found him when I was 13

I had heard about Letterman from a cool family friend (David Mendelson), but I had never stayed up to watch him myself until I came home from some classmates bat mitzvah (Chloe and Lindsey Weil — twins). I was in 7th grade, and for many these Jewish celebrations mark the beginning of what 13 year olds would say were their real teenage years. I came home from some “partying with my friends” to a house asleep. I was my own man: I turned on the TV and found Late Night with David Letterman.

It was subversive, weird and ironic, unlike any other place in culture. I felt welcome. The host made fun of his bosses at NBC, which was a useful bit of evidence for a kid picking fights with his teachers at school.

Letterman hated phonies in a way that every careful reader of Catcher in the Rye would immediately recognize. He had a sometimes flirty, sometimes combative on-air relationships with guests.

He celebrated the oddball

As always, and for no apparent reason, here is Larry “Bud” Mellman:

It was like nothing else on television.

Here’s what Conan O’Brien said the other day:

Dave’s show was that rare phenomenon: a big, fat show business hit that seemingly despised show business. Dave didn’t belong, and he had no interest in belonging. He amused himself, skewered clueless celebrity guests, and did strange, ironic comedic bits that no one had seen on television before. Everything about that show was surreal and off-kilter. Where late night television had once provided comfort, this man reveled in awkwardness. Cher called him an asshole. Andy Kaufman ran screaming from the set. Chris Elliot lived under the stairs. Throughout one episode the entire show rotated a complete 360 degrees, for no reason whatsoever.

And here is Cher calling Dave an asshole:

For me, my obsession to David Letterman in high school and college consisted of taping every show, ordering away for “late night” t-shirts, and reading every interview I could find in a pre-internet world. I talked to everyone about the show, even if they didn’t show much interest.

I wrote countless letters to Viewer Mail (and got one on in 1991). I applied for internships with the show. I moved to New York to be a CBS page. And I positively mimicked a certain sense of humor.

Tina Fey breaks down a whole class of guys like me:

For my generation, Dave completely defined the way we spoke to each other. I didn’t meet one boy in college who wasn’t talking in Dave’s cadence and ripping off his style.

Eventually I stopped watching Letterman

I guess I outgrew him, or moved on to other things. And honestly I don’t think the Letterman show has been particularly funny or innovative since he moved it an hour earlier at CBS in 1993. His new show had energy in those early CBS days, but the host was broadening his show — he wasn’t groundbreaking and subversive any more.

In the intervening years we got cable TV and the Internet. If you’re looking for the innovative voices in comedy (and in the writers room) they’re everywhere. For me, I spent more time following Jon Stewart, Stephen Colbert, Amy Schumer, Eric Andre.

Letterman in the last decade has been phoning it in. And he’s had his own struggles: He had quadruple bypass and scandal. He grew older, got married and had a kid. He mellowed out a lot on the air. He got bored as he approached 6,000 hours of TV.

Yet he still showed up with moments every now and then: he still skewered the self-absorbed. Along with Jon Stewart, he showed us that there was a time for a funnyman to be as direct and genuine as much as any journalist, as he did on his first show after 9/11.

I’ve come back to being a loyal viewer of Letterman again only in the last few months. I have watched A LOT of his old NBC show on YouTube.

And I reconvened with my old CBS page colleagues for a visit to the Ed Sullivan Theater one last time last month. It feels very fun to be solidly back in his fan base.

As his show winds down his longtime celebrity friends are coming back to pay homage to their old uncompromising friend, much as they did for Johnny Carson a generation ago. And Letterman is having fun for the first time in years. You can still see that sharp, distinctive and insecure mind still at work.

For me, this all brings a distinct wistfulness to the proceedings. It’s not just me reflecting on what David Letterman’s retirement means to culture. It’s what it means to me. You can see a bit of this in appearances like Adam Sandler’s this week. The big four networks don’t mean anything any more, nor do any of the institutions that we all grew up with. Where has all the time gone since we first found David Letterman?

He’s a legendary, brilliant and really funny broadcaster.

30 years have gone by.

His retirement means we’re not teenagers any more.

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