Vitalik would definitely be most interesting one, but i think he would get bored with me as i wouldn't probably be intellectual enough to have a chat with. Andreas Antonopoulos would be most entertaining to listen to, he thought process seem to be so well structured that he is relaxing to listen to. For fun jet set night i would probably choose Cryptocobain, he seems to have a right idea for partying with money.
interesting point of view. We could tie Vitalik to a chair, though. Or, yes, just gather a few other people in addition and basically just watch them discuss and only drop in a question every once in a while.