Returning to this (again).. "if there was still a phone book" relates to our modern (digital) times where no phone books are necessary anymore, isn't it? So it is narrated from a modern, today's point of view, when he speaks about the cool kids and the venues are closing down? Still seems to me that (some sort of) a producer is talking to his artist, but it must be somebody who sang earlier, too but is not appreciated anymore.
So all those ideas about Bob, Elvis, Joni, Emmylou and Leonard are all wrong.
LE