The Sound-Money Library
Sixteen books, two centuries. The intellectual lineage that ends in Bitcoin runs from Bastiat in 1850 through the Austrian School and Friedman's monetarism, to Saifedean Ammous and Nick Szabo in the cryptographic era. Each entry here is a deep read: thesis, summary, the most-quoted passage, an explicit Bitcoin-relevance section, and where to read the book free or buy it.
How to read this list. If you've never read any of these, start with Hazlitt's Economics in One Lesson (a single afternoon) and Rothbard's What Has Government Done to Our Money? (also short). Those two cover ~70% of the framework you need to read Ammous's Bitcoin Standard productively.
If you want the deep cypherpunk lineage, read Szabo's Shelling Out and Bit Gold before you read the Bitcoin whitepaper — they make Satoshi's actual contribution visible by showing the design space he was working within.
Continue to the economists, the quantitative methodology, or return to the main thesis.