Books
The reference texts worth owning, the narratives worth reading, and where to look when both run out.
A short list rather than a long one. Everything here I have actually read, and I have said why in my own words — go to the publishers for the real thing.
The reference
Options, Futures and Other Derivatives — John C. Hull. The standard text, and standard for a reason: it is the book desks actually keep on the shelf. Not a book to read cover to cover. A book to own and open at the chapter you need, which for most people is binomial trees first and the Greeks second.
Option Volatility and Pricing — Sheldon Natenberg. Where Hull gives you the mathematics, Natenberg gives you the trader's intuition for what the numbers mean when the market is moving. If you only read one, and you intend to trade rather than to price, read this one.
Dynamic Hedging — Nassim Nicholas Taleb. Difficult, opinionated, and written by someone who ran the risk rather than modelled it. Worth the effort specifically for its treatment of the places where the standard model quietly stops working.
Narrative and memoir
The textbooks tell you how the instruments work. These tell you what happens when people use them.
Liar's Poker — Michael Lewis. Salomon Brothers in the eighties, and more or less the book that invented this genre. Everything below is in conversation with it.
The Big Short — Michael Lewis. Sharper than the film on the actual mechanics of the trade: what the CDS contracts said, why the counterparties kept writing them, and how long being right can take.
Flash Boys — Michael Lewis. HFT and market microstructure. Contested by practitioners on several points, and still the most readable route into why venue design, latency and order routing decide who gets filled.
When Genius Failed — Roger Lowenstein. The definitive account of LTCM: a quant fund with the right models blowing up on a liquidity constraint and a correlated market. The relevant lesson is not that the mathematics was wrong.
Fool's Gold — Gillian Tett. The JPMorgan team that invented the credit derivatives later used to blow up the system. Narrative rather than textbook, and unusually good on how a well-intentioned instrument gets away from its authors.
On risk, more broadly
Against the Gods — Peter L. Bernstein. A history of how humanity learned to measure risk at all. Useful perspective on why the tools look the way they do.
The Black Swan — Nassim Nicholas Taleb. Overexposed and still worth it, if you read it as an argument about the shape of distributions rather than as general-purpose contrarianism.
Engineering, for the systems underneath
Designing Data-Intensive Applications — Martin Kleppmann. Nothing to do with options, everything to do with building the systems that price them. The chapters on consistency and stream processing are the ones that mattered to me when we were building risk engines that had to be correct at a million updates a second.
Where else to look
The exchange documentation is better than most books for mechanics — specifications, margin methodology, contract terms. It is dry, free, and authoritative, which is a rare combination. If you want to understand SPAN margining, the exchange's own methodology paper will teach you more in an hour than any textbook chapter.