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Handicapping Books -
The Handicapper's Condition Book - James Quinn
This book is a great introduction into the intricacies of class and the "class within the class".
The Winning Horseplayer - Andrew Beyer
Picking Winners - Andrew Beyer
Both of these book are considered seminal handicapping book, especially with regards to speed figures. Whether you end strongly considering speed figures in your handicapping, or you think they are useless, I think these books are critical reads due to the overwhelming use of figures in the game today. In my opinion, understanding how figures are created, and the judgements that one must make in order to calculate and apply the numbers, is a cornerstone of handicapping.
Pedigree Handicapping - Lauren Stich
I'm not sure if this book has been updated in the past several years; if it hasn't, some of the sire lists will be out of date and a little stale. Still, I think this is a good read if you want to understand more about the impacts of pedigree on racing performance.
Betting Thoroughbreds - Steve Davidowitz
An excellent book for the intermediate or advanced player. Probably not a book you want to dive into if you are just starting out in the game.
A solid book but probably not my favorite book by Beyer. Read this one if you've already completed The Winning Horseplayer and Picking Winners.
This book has nothing to do with handicapping or picking winners - it's all about bet construction theory.
A really good book if you are just starting out in the game. Brad Free does an excellent job of breaking down and explaining the fundamentals of handicapping and wagering.
Modern Pace Handicapping - Tom Brohamer
One of the seminal works on pace and pace handicapping.
Money Secrets At The Racetrack - Barry Meadow
If you like to play exotic wagers, this is a really solid book on bet construction.
Books on Great Horses -
Ruffian: Burning from the Start - Jane Schwartz
A wonderful biography of one of the most tragic racing figures in the last half-century, Ruffian.
Secretariat: The Making of a Champion - Bill Nack
The DEFINITIVE biography of one of the greatest thoroughbreds of all-time by one of the best turf writers of all-time, Bill Nack. Buy it. Read it. Love it.
General Horse Racing Stories and History
The Best and Worst of Thoroughbred Racing - Steve Davidowitz
I really enjoy Davidowitz's writing style and this book is no exception. This isn't a handicapping book but merely a collection of stories about the sport we love.