I just don't "get" Letterman, I guess.
I'm going to use a "pot of funny" analogy here and see how far it works.
So, you've got these laugh-a-minute guys that are constantly over the top - they're chucking rocks into the pot of funny. Eventually, all the funny's splashed out and the noise is getting annoying.
Then you've got these simmer-splash guys that take a while to set up a joke and knock it down. That's usually alright because there tends to be some informative bits as they're building the tension.
Then you've got the "low boil" folks that just rumble along with a subtle delivery, rarely going for the big laugh, but keeping those smaller jibes and ironic statements flowing. Maybe you have to lean in a little closer and pay attention to catch it. I dig low-boil humor.
To me, Letterman is just...sitting there. Like - where's the entertainment? Where's the funny? I hear the audience laughing - I know it's supposed to be funny. People laugh, and I look at the motionless pot of funny going, "did I miss something?"

"Did I miss something?"


Yes I think you did Rev. Letterman is a master. Think about how incredibly difficult it would be to make responses to this crisis: make your point, rag hard on an old friend, offend your bosses, name drop your competitors, rag on them, keep your dignity, keep your job, make fun of people that aren't even involved. Now do all this with a seemingly off-handed ease of a simple late night drunken conversation among friends that you somehow managed to pull off famously.


It's a natural talent refined by years of practice and enjoyable to watch.

To my taste, just because something is difficult does not make it entertaining.

For letterman, and many of the late night talk show guys (Carson et al), it's not about the "funny", as much as personality. They're TV Personalities, so while they can turn on the skills to get the laugh a minute, they're all around charismatic in general. If you don't "get" it, it's most likely because you're just watching for the comedy and don't really care for the general commentary. They're TV's radio DJ's, essentially.