Which books should you read one hundred times or more?

No, not your own.  Here is one view:

The main effect of reading Hamlet a 100 times was, counter-intuitively, that it lost its sense of cliche. “To be or not to be” is the Stairway to Heaven of theatre; it settles over the crowd like a slightly funky blanket knitted by a favorite aunt. Eventually, if you read Hamlet often enough, every soliloquy takes on that same familiarity. And so “To be or not to be” resumes its natural place in the play, as just another speech. Which renders its power and its beauty of a piece with the rest of the work.

That reader is Stephen Marche, the link is here, interesting throughout.  Can you guess which is his other pick?

By the way, I believe that to do this you need to own many copies of the work (can you figure out why?), and indeed Marche owns at least ten copies of Hamlet.