One of my favorite quotes from John Cage is from his Lecture on Something, in which he mentions in passing about why rankings — "First, Second, No Good" — of creative works amounts to being the hobgoblins of small minds.
Most of the talk about what comes first, or what is best, is little more than a way for people to find something to put on a pedestal. Perhaps they want something to look up to; perhaps they want to have other people look up to it; perhaps they want to take credit for recognizing the greatness first.
All of these reasons strike me as small-minded and unimportant. Lists of ten, fifty, or one hundred best are interesting for the sake of a perspective you didn't have before, but not because they constitute some kind of stack-ranking methodology to figure out what order you must encounter those things in before you die.
I've come to find this approach all the more obnoxious as time has gone on, because it tries to take the whole matter of encountering creative work — which is by definition a messy, haphazard business — and turn it into a mere five-foot bookshelf experience, a manicured garden of the mind.
Understand that I'm not talking about the idea of doing away with hierarchy as a useful organizational or problem-solving tool. Sometimes you need to have an order of operations, lest you drown in an ocean of irrelevance. And some things are useful to know about for the sake of having a context — e.g., most anyone who sneezes in the general direction of SF should read Dune or The Foundation Trilogy, just so they have some idea of what went on in this books. None of that is a problem.
What I reject is the idea that such rankings can serve as a shortcut to developing one's own taste and discretion — that one's taste is a matter of simply receiving the right things in the right order, not by what sort of struggle one brings to any given encounter. List-based culture is an embodiment of the sort of middlebrowism that Dwight MacDonald resented, where the business of engaging with culture is turned into a mere IKEA instruction manual, and where being able to fake one's interest in something is supposedly more useful than a sincere "I don't know."
Sincere ignorance can be cured sincerely; contrived understanding resists almost all medicine, especially the sincere kind.