Nah, not at all. He was hilariously brutal as the host of Buzzcocks. He's trying to be a genuine human being and for people who remember him on the show it does come off as awkward.
Yes, Simon Amstell, he is literally on "Conan", the talk show hosted by Conan O'Brien. I don't quite understand your incredulity here; a lot of people appear on that show, and Mr Amstell is a fairly well-known young comic.
No, obviously the description means "Simon Amstell on the topic of Conan", implying that Conan O'Brien is the well-oiled dungeon boy of Simon Amstell's dreams.