Jay was a real good standup comic way back when. He was a good replacement for Carson as his style was similar to Carson's, but neither he nor Carson are/were as edgy as Conan is. I really wonder what will happen when Conan takes over the Tonight Show, I think he'll lose much of his edge, it being an earlier timeslot and all.
As for who replaces Conan:
Carson Daly: No frickin way! I only watch his show when a good guest is on, even then Carson is a mediocre interviewer most of the time and if he has a politician(or a celebrity expressing a disagreeable political point to Carson) on that he disagrees with Carson gets all fuddled up. I wish he'd quit trying his opening "Jokes", he just can't tell a joke if his life depended on it.
John Stewart: He'd be great and I'd love to see him take over, but I think he's too big for that time slot. The Late Show is more of a training ground for up and coming types, not established talents.
Andy Richter: I think he'd be good, but I don't see it happening. I just wonder if he could bring his own uniqueness to the show or whether all his ideas have and are already been/being used. I think it is imperitave that whomever takes over has to be edgy and the only way to be edgy is to come with new ideas.
Tom Green: He did some hilarious things on his show, but half the time he goes over the edge. He's like a bad car accident, you feel compelled to look, but often what you see is revolting.
Jimmy Kimmel, Craig Kilborn: Wannabes. Watched them both and though they are both ok talk show hosts, I find them generally dull and rather run of the mill in style. Kind of reminds me of the early 90's when Late Night Talk Shows were being handed out to everybody, many were good, but most were clones of each other(Arsenio was really the only one back then that brouht something fresh and even he couldn't survive). Boring.
Letterman and Conan were both nobodies that turned out great and very envelope pushing(Letterman was the man back in the '80's just like Conan is today). I suspect the person who takes over Conan's spot will be similar. I'm not really sure if I want this to happen as Conan will have to tone things down. OTOH, by that time he probably will have lost much of his edginess like Letterman did before him.