I was a huge Letterman fan back in the 80’s. I still have a VHS tape recording of the very first episode on NBC in (I think) 1982, with Bill Murray. Those were the days when he was crushing stuff with a steamroller, throwing things off the NBC roof (he still does that occasionally, but it’s not as funny any more), and bringing on very strange guests like “Brother Theodore”. Brother Theodore was awesome. He’d rant at Dave like this:
“I hate you. You are slime. You wil return to the dankness of the earth and rot, and rot, and rot, AND ROT!”
Dave: “Is that a Ban-lon shirt you’re wearing?”
One of the things that has happened to Dave is that his quirks and tics have aged into strange personality flaws. Bizarre stuff in a 30 year old comic winds up vaguely creepy in someone pushing 60. Does anyone remember when Norm MacDonald did his devastating impersonation of Letterman on SNL? He would spend the entire show mugging, pulling his collar with his finger, making strange noises, and it was perfect. Dave has pulled it back from there (maybe as a result of that impression), but as a result he’s lost his edge.
I think this is a particularly dangerous thing for comedians - trying to age gracefully while still maintaining a comedic edge. Conan is really susceptible to this because much of his humor revolves around mugging, strange quirks, and basically showboating in front of the camera. I don’t want a 60 year old Conan calling the crowd “My Babies” and banging his hips around. It’ll just look stupid.
Some comedians manage this by essentially morphing out of comedy - Robin Williams and Steve Martin, for example. Can you imagine Steve Martin doing ‘happy feet’ and his wild and crazy guy thing today? It would just be sad. So he’s matured into an actor/writer who moves from romantic comedy to drama. He’s been very successful in that transition. Robin Williams, not so much. He still tries to be the crazy 20-something coked-up Williams, but it usually just comes off like a parody of himself.
The trap talk show hosts are in is that they have no path to a more ‘mature’ career. They have to keep doing the same things they’ve always done, or find new funny things that they can grow into. Carson managed it very well. Letterman has stumbled along the way. Jay Leno I suppose managed it - does anyone rmember the young, angry Jay? The guy that would do the “What’s my beef?” schtick? He was hilarious. One of my favorite comedians. Now he more like your mildly amusing father. But the angry schtick is hard to pull off when you’re 55 years old and making millions of dollars a year.
I think Conan is really at risk here. That transition to the Tonight Show is going to be tough. In his favor is intelligence - he’s probably the smartest of all the Late-night hosts, except for maybe Jon Stewart. Also in his favor is that at heart he’s a comedy writer who got his start on the Simpsons and SNL, and he has a great ear for comedy. But he’ll have to morph into something new to stay viable, IMO.