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To help capture the spirit of the question, I will elaborate here at length on what I mean. I ask as a reaction to 'How to Read a Book' by Mortimer Adler. He uses this question as part of his explanation for why the 'Great Books' are great. I interpret him to mean that the truly great books are worth re-reading over the course of one's life. To me, this suggests that 'King Lear' is genuinely better on the 10th read. So, the initial criteria is which books retain their entertainment value. But what I am more interested in are which books seem to continue to enrich one's experience. For Terrence Tao, this would likely not include any expositional math books as he could absorb all they have to give. But it may include a book of longstanding math problems. So the question is which books could one continue to learn from for the rest of their life? I have read quite a bit of philosophy and most of the works I like don't quite fit this mould. I generally figure that if an author had something valuable to say they would have said it clearly. But maybe something like David Deutsch's The Beginning of Infinity would allow me to dream of the end of invention for the rest of my life. I hope that this question gets responses that allow one to prioritize the reading that they do for the sake of personal enrichment, in the broadest terms. I am the sort of person who listens to books at 2x speed and only finishes about 1/20 books I start, because I am keenly aware of the pareto distribution of reading quality. But as we still don't quite have a great answer to the question of what is valuable and what world do we want to aim for, I still think toiling over 'The Iliad' and 'Paradise Lost' might be a good use of one's time, all things considered.