I'm a big David Letterman fan. I don't stay up and watch often, but when I do, Dave comes across to me as great curmudgeonly old friend. He's got a unique schtick. Often his jokes aren't really jokes. Sort of a weird post-modern type of comedy.
One quirk which for years drove me batty: Monica Lewinsky jokes. Years after Clinton was out of the White House, Dave was still reaching back to the Lewinsky well.
I mean, sometimes it was funny. But Dave seemed sort of obsessed with INTERNS.
Well it turns out it was kind of a Freudian thing...