Henry Blodget: The Wall Street Self-Defense Manual
What you need to know before you invest.
Jeremy Siegel: Stocks for the Long Run
An excellent overview of asset returns.
Charles Ellis: Winning the Loser's Game
Think you can beat the pros? Don't be silly. You can't beat the pros in baseball or football, and you can't beat them in the stock market. Unless you play a different game.
Burton Malkiel: Random Walk Down Wall Street
The market is not "random," but most stockpicking success is.
David Swensen: Unconventional Success
Yale's superb investment officer sounds off on the mutual fund industry: "The systematic exploitation of individual investors requires government intervention." N.B.: He's not talking about market timing.
Mark Hebner: Index Funds
A tour of investment theory, with an emphasis on the futility of stockpicking. Hebner is a self-taught advisor, which helps make him a good teacher.
John Bogle: Common Sense on Mutual Funds
Don't buy a mutual fund until you have read this book. If your broker hasn't read it, get another broker.
Peter Bernstein: Against The Gods
"The Remarkable Story of Risk." Shows how (some) humans learned to distinguish luck from skill, assess probabilities, and intelligently play the odds.
Michael J. Mauboussin: More Than You Know: Finding Financial Wisdom in Unconventional Places
A collection of essays by the most well-rounded, original-thinking strategist on Wall Street.
Robert J. Shiller: Irrational Exuberance
Excellent study of the many factors that contribute to booms and busts. Shows why both happen, as well as how long full cycles take (40 years).
Robert Hagin: Investment Management
Shows why many people who think they are good investors are hallucinating.
Benjamin Graham: The Intelligent Investor
Like his protege, Warren Buffett, Graham was a true guru. A pleasure to read, but don't imagine you can follow in Graham's footsteps just by reading it.
Dimson, Marsh, and Staunton: Triumph of the Optimists
Expensive and academic, but excellent detail of 101-year performance of 16 markets. Shows that stocks don't perform as well as most people think.