I don't think Letterman has to worry about his ratings. Hard to say how Conan will do. I think Leno was very lucky to have Kevin Eubanks as both a very talented band leader and a very likable sidekick of sorts, whereas I can't stand Paul Shaffer. Max Weinberg is a great musician, and they did some funny things with him, but he was not a real sidekick. I like Andy Richter, but they definitely need to tone him down a lot. I thought the cross-country bit was generally pretty funny, though long. I didn't think the monologue was terribly funny....
I like Conan OK, but his monologues have always been very short, and the bits that followed were very uneven. I very seldom watch the guest segments. (And I don't like Will Ferrell, so I turned it off at that point and got back on with Pearl Jam--who were pretty good.) I'll probably watch Conan from time to time, but I may well just tape Leno and watch him then, I dunno.
While I'm on the subject, I still really haven't watched Fallon at all. But from what little I have seen, I wonder if he has a dynamic enough personality to pull it off. From what I've heard, at least the writing is pretty funny. And I still can't believe he got The Roots! But I do like Ferguson best. It amazes me what he does with what little they give him.
I just never got in the habit of thinking about ABC late nights. I don't even know when Jimmy Kimmel is on. I like him, but you can only watch so many talk shows. However, I do think, of all the people I've seen, he would be the best replacement for Regis. I don't know if there would be more money in it for him there or not.
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