Rothbard's Anatomy of the State certainly comes to mind (free download via Mises: https://cdn.mises.org/Anatomy+of+the+State_3.pdf). It definitely has you question everything you were taught in formal schooling.

I read Howe & Strauss's Fourth Turning last year and it blew my mind. Love the framing. Really makes you think about where we're heading and the role Bitcoin can potentially play.