The overall best book I have read about challenging the world and how we see and interact with it is Stranger in a Strange Land by Robert A. Heinlein.
Reason: It is written in a way that pokes at the reader to question the society they live in and see it in a new light, and to realize that many of the norms are only normal when seen through the context of repetition and the savage backlash by society itself when someone attempts to show them a better way.
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Contributor: Lisa Orban | Twitter