Letterman is a quirky character. The only thing he does that's funny is his top ten list and that's written by someone else, no doubt.
I've never seen what the big deal was about Letterman and I don't know how he rates having his own show.
I thought he set a real bad example when he didn't marry the mother of his child. They've lived together for over ten years and supposedly have a great relationship. I suspect he likes his money too much to part with it in the event of a divorce and a pre-nup is probably out of the question.
It's beyond me why any woman would want to stalk such a jerk. But then again, lots of women go for jerky guys.
Go figure.