Dont forget Andreas Antonopoulos. Any of his old podcasts or speeches are great. "Mastering Bitcoin" is also a great resource: Even if all the nuance does not click, it provides a comfort and familiarity.

Then, for a fun read with more modern (ie, post cypherpunk, bitcoin coming of age) history, try "Bitcoin Billionaires."

While already mentioned, the Bitcoin Standard is great for economic history and allows for an understanding bitcoin's value proposition for human action.