The Chinese Room argument seems to me so deeply misguided and silly that I doubt an interesting dialog on it is possible, any more than a fruitful discussion of religion with a well-educated theist.
I know little of his work other than the aforementioned argument, but it doesn't really paint a flattering picture of his ability to engage in clear thinking.
Searle's actually pretty brilliant and he's mostly on the right side on this one. When you cast the debate as between Searle and Dennett, Dennett is obviously right. But in a broader context, Searle and Dennett are on the same side.
But I agree that there's no reason to talk about the Chinese Room. Either you're convinced by Dennett, or there's no use talking further about it.
Bloggingheads.tv can't exactly call up, say, the President of France and get him to do a diavlog, but they have some street cred with mid-rank celebrities and academics. With that in mind, how would you fill in this blank?
"I would really love to see a diavlog between Yudkowsky and ____________."