Point of View

My Road Trip with David Letterman

For decades, broadcast television has peopled our lives with folks joining us in our living rooms, creating a curiously one-sided intimacy.

When I heard that David Letterman was retiring, I couldn’t believe it. It’s impossible to imagine a television landscape without him. Most nights he was the last person I saw before bed: in my living room when I was a kid; then as a teenager; and now as some kind of pretend adult-thing as it’s coming to an end.

It was on a road-trip to Mexico that I first saw Late Night with David Letterman.
Though I always wanted to, I’d never managed to do Mexico by road again until right now. Here I am, finally in the midst of that trip, right when Letterman’s run on the Late Show is coming to an end. It feels like a long and personal circle is being closed.

That childhood road trip was significant in my life not just because it was my introduction to Mexico, but because it was a rare thing in any case; it was the only one we ever took as a family.  But it was a good trip, a wonderful trip. And it had to be, because there weren’t going to be any more of them. Too soon after, my father died.

As a kid I adored stand-up and sketch comedy, and in adulthood, when I started spending time with stand-ups and writing and performing Improv myself, I came to realize that my father watched comedy like a comic. That is to say, he wasn’t an easy laugh. We’d watch comedy together and I’d check his reaction. If he thought it was good, usually he wouldn’t laugh, but he’d watch with focus and say, “That’s really funny”. If he said that, I knew it was. If he actually laughed, then I knew it wasn’t funny; it was hilarious.

One night on the road to Mexico, in a motel room in Texas I think, Dad and I found Letterman on Late Night doing a bit on toys and games for little kids.* He was in a store and getting the guy to show him how some of them worked. Letterman veered between deadpan and sarcasm as he would check out a game and say things like “This is for kids? Kids like this? But this is just crap.” Dad and I reacted like we couldn’t believe our eyes; he fell apart. Dad laughed out loud? My God. Then David Letterman was hilarious. Finally, someone on TV was telling the truth, telling it like it is, making the kind of sarcastic jokes we made to each other. In short, Letterman was speaking our language, and no other PR-vetted talk show host was doing that.

Dad and I shared a lot of eye rolls at cheesy TV. It was from him I learned that cheap sentimentality was indeed cringe-worthy; but genuine emotion and real feeling were not and had value. That there was such a thing as good writing and bad writing. David Letterman was a breath of fresh air because he was the antidote to the phoney; to cheap, hollow, audience pandering, to playing to the lowest common denominator.

Besides, he was funny, and his musical guests were cool.

Letterman took flack for his approach to hosting the Oscars in 1995. I couldn’t understand it. Hollywood is about the movies, but its major awards show is television, whether they like it or not. He was the perfect host I think. I’ve always loved movies enough to watch the Academy Awards, but Jesus, sometimes the self-importance, the puffery, is puke-inducing. Before HBO and AMC, Hollywood used to love to condescend to TV as its poor relation, and you could feel the icy chill that settled on the crowd of stars and executives when they realized that Letterman was not greasing their hot air stuffed shirts, he was lampooning them. But they took him all wrong I think. He wasn’t lampooning them, he was throwing a dart at the hot air balloon of the event. It was the Oscars for God’s sake. They should’ve been big enough to to take it.

During Dave’s last week on air, I’ve been in a different motel room every night. Imagine the panic: “is this a dog-friendly motel?!? Do you get CBS?!”

Not that he’ll see it, but Letterman would probably wince at this piece of course. But, that’s okay I think. Emotion, not sentiment. In the end, who doesn’t want to be told that they matter? That they gave you something? That they’ll be missed?

I’ve learned to live with the Dad-shaped hole my father left when he passed, partly by trying to fill it with the things we shared that live on. Like apoplexy and scotch, comedy and Letterman are consistently good things I have used to try and fill that hole.

Letterman’s funny, he’s an original, he changed the format. He never operated below his intelligence, but also never stopped being a plain old goof-ball. He gave us the chimp-cam. Priceless banter with Jack Hanna. Stupid pet-tricks. Good Lord, The Top Ten List.

So it was a good show, a wonderful show. And that’s good, because there aren’t going to be any more of them.

*If I could find it, I’d share a link here. I suspect it was an episode dated early-mid March, 1983.


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  1. Sharon Coates says:

    nice, Samantha! Liked your musings. I missed almost all of Letterman, mainly because there was no way I could stay up that late, go to work the next morning with an alert brain. How’d you do it? We’ve been pvring lately and so can see them when we want!

  2. Samantha Swan says: (Author)

    My answer to how I do everything, Sharon: lifelong insomniac.
    It’s good you’ve got some of the recent shows to see. You’ll also be able to watch some older episodes – or at least clips anyway – online on Letterman’s YouTube channel.

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