Get a Financial Life - Beth Kobliner -?The best source I've found for easy to read, easy to understand, end to end coverage of all the major aspects of personal finance. It's quite short, so it can't be comprehensive, but at least it covers the basics and will get someone moving to take control over their financial life. I think it should be impossible to get a high school diploma without having mastered everything in this book.
The Investor's Manifesto - William Bernstein -?A fantastic romp through the investment world. It's extremely readable and provides a lot of information that helps the reader understand how modern personal investment got where it is and why it's so hard for us to win at the personal investment game. It also provides some really solid advice (that I don't completely agree with, but that's another story) on how to build a portfolio.
Much of modern theory on portfolio construction is based on the assumption that stock markets follow normal distributions or other equally predictable distributions. We've known for a long time that this idea is just wrong but you'll be hard pressed to find many books that discuss this because the implications for predicting the future are fairly scary. But closing our eyes to reality isn't a recipe for success. Which is I strongly recommend the next book.
The (Mis)behavior of Markets - Benoit Mandelbrot & Richard L. Hudson -?Yes, that Mandelbrot, the father of fractals. A walk through the history of modern financial theory. Followed by an exploration of why market behavior appears to be fractal and why that insight may be useful for science but not for building portfolios. The main insight is that you can't predict anything about the future of finance which means we are planning our portfolios blind.
The next book is also an attack on what passes for financial orthodoxy on Wall Street. Maybe stocks and most bonds aren't a good idea at all? No, this isn't some crazy spiel about gold. It's something much more socialist than that.
Worry-Free Investing: A Safe Approach to Achieving Your Lifetime Financial Goals - Zvi Bodie & Michael Clowes -?Dr. Bodie is one of the leading researchers on life cycle investing, he got his PhD from MIT, is a professor at Boston University and has served on the finance faculty at Harvard Business School and MIT's Sloan School of Management. So this guy isn't some wacko. His book proposes that perhaps you can retire just on TIPS bonds, social security and perhaps some stock options. I'm not completely sold but I do use the ideas in this book as a building block of my portfolio.
The last three books don't have anything radically new to say. But they cover ideas touched upon in the previous books in a lot more detail. So, dear reader, if you actually enjoyed reading the previous books then these books will probably be a lot of fun and help you understand the finance (that your life and the life of your family actually does depend on) a lot better.
A Random Walk Down Wall Street - Buton G. Malkiel -?This is one of the grand daddy's of personal finance. It's updated every few years so make sure you have the latest copy. It provides a ton of background and information on how modern finance works. I have read three different versions of it cover to cover and with a new version out this year I'll probably be reading it a fourth time.
Common Sense On Mutual Funds - John C. Bogle -?I don't think it's an exaggeration to say that Bogle was one of the most important people to drive personal finance in America in the last century. He was the driving force behind indexing in general and Vanguard in particular. This book is his manifesto on investing. I actually think this book is better in terms of content and coverage than The Investor's Manifesto but it's also a lot longer and I think the Investor's Manifesto hits the key points in a lot less space.
The Black Swan - Nassim Nicholas Taleb -?This book explains the ideas behind the 'black swan' and why it drives so much of what happens in our financial markets. In theory if one is smarter than me then all the ideas in this book would pop for free out of Mandelbrot's book. Which isn't surprising since Mandelbrot was Taleb's mentor. But if your as dumb as I am reading this book helps to drag out a bunch of key insights into why finance is so unpredictable.