Good night to David Letterman

Being a freelance illustrator often means staying awake into the wee small hours to get your work done. And for me, part of staying up late meant having David Letterman as company, especially in the decades before Netflix streaming.

This caricature of Dave and Paul was in my portfolio back in the late eighties.

As I watched his last show I was awash in nostalgic feelings, and I’m not even sure why because I haven’t really been watching the past couple years. Part of the reason must be that the 33 years of his show being on the air has kind of paralleled my time as an illustrator.

I was one of the dozen or so people who watched his morning show that preceded Late Night in the summer of 1980, right before I started at Pratt Institute. In 1982 when I heard he was getting a nighttime show after Johnny Carson I remember telling my roommates that we should check it out. Almost instantly the show became an integral part of staying up late and getting work done.

David Letterman’s sensibilities influenced my generation’s humor and perspective in the way that Monty Python and Saturday Night Live had a few years earlier. Phrases like “we all know how painful THAT can be” and “no wagering please” would pepper our speech, replacing “this parrot is most definitely dead” and “We are two wild and crazy guys!”

Dave gave us permission to view the hip and the avant garde with detached irony. But was he a regular guy chuckling at the pretentious elite? Or was he an elitist himself? I used to love it when Harvey Pekar, the underground graphic novelist came on the show. Dave and he would get into verbal sparring matches, and Pekar came off looking like an eccentric lunatic. In recent years I’ve discovered Pekar’s work and grown to appreciate his writing. Now when I watch those old interviews on Youtube Dave seems like a frat boy being really condescending to an alienated nerd.

 

In a strange way that’s another aspect of the show that I relate to. Before I embarked on illustrating 140 chapter books I thought social satire would be my illustration niche. I wanted (and still want) my illustrations to be funny, but not sarcastic. Social satire is at its best when it’s pointing out something that we recognize in ourselves (and laugh at), rather than pointing at, and putting down, in someone else. I think Dave aspired to that too. True, he often fell short and came off as sarcastic. And if his humor was condescending at times, he was self deprecating in equal measure. But I think it’s remarkable how often his humor hit the perfect mark, insightful but never sentimental.

Older Dave