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Fienberg and I argued last night about how surprised Jay could have been, given that he knows Jimmy's MO. My feeling is that Jay looked clearly upset by the end of the segment, and he's not a good enough actor to fake that. So either he expected Jimmy to be nice, or he expected Jimmy to get in one or two light zingers, but nothing this extensive and cutting.
There seemed a point a while back - circa the Matt Damon and Ben Affleck videos a couple of years ago - when it seemed like Kimmel was inserting himself into the late night conversation as more than an afterthought. Then NBC announced what we now know to be the idiotic baby-splitting plan of Jay at 10 and Conan at 11:35, and that was all anyone could talk about in late night. But I think after this double-whammy on Jay, Kimmel's going to be impossible to ignore.