100 Books Like A Random Walk Down Wall Street

As everyone knows at this point, anything Michael Lewis writes will be enormous fun to read, while being about something really important—something he’ll make you care about even if you didn’t when you started the book.

In this case, the subject is people who bet on the direction of mortgages (and thus, house prices), and how those who bet on a huge plunge were right. This book has an amazing cast of characters, all richly drawn: some are smart, some are not so smart; some are excellent schmoozers, some can barely tolerate human interaction; some care a lot about money, some care more about being right, especially if everyone else is wrong.

Each book I've recommended cries out to be made into a movie. This one actually was.

Another book on money. I couldn’t have survived the leaner times as an actor without the lessons in this book about how important saving money is. It seems logical, but most people don’t do it or don’t do it correctly.

This book helped me to further increase my financial acumen. What happens to a successful actor who knows little about money? He loses his house and his car and loses out on great opportunities. I vowed never to be that type of actor. I vowed to be the entrepreneur that I know I am.

I’ve never found a book that lays out the whole-life approach to success as well as this book.

I was particularly impressed by the emphasis on things like marriage and masterminds—the impact those have on our success in life is often overlooked. It gave me a solid framework to look at my own life and see what areas I needed to focus on more, and I consider this book a big part of my success in life.

To build wealth, we need an environment that allows for unequal outcomes. The Friedmans argue that using societal or governmental force in the name of equality will destroy the environment where we are free to choose how wealth is grown. In their words: Freedom “preserves the opportunity for today's disadvantaged to become tomorrow's privileged and, in the process, enables almost everyone, from top to bottom, to enjoy a fuller and richer life.” Let the market determine the outcome. Bad ideas will wither away, and good ideas will thrive.

Life expectancy among the working-class population in the United States was decreasing at an astounding rate well before the Covid-19 pandemic. While I was aware of growing inequality and decreasing access to health care for many, I didn’t realize how desperate the conditions of life seemed for many working-class Americans.

This book forced me to confront the uncomfortable reality of the health crisis among the many blue-collar workers living in the heartland of America.  

Who knew that a book on tax reform could be so interesting? Showdown at Gucci Gulch, which tells the story of the 1986 federal tax reform, remains the best in depth look at how a bill really becomes a law, including a cast of interesting characters, from Ronald Reagan to Dan Rostenkowski. The book is also a good primer on what a good tax system ought to look like and how myriad special interests invariably oppose such a system. Murray and Birnbaum were reporters for the Wall Street Journal who covered the 1986 tax reform and write with a reporter’s eye for detail. Really, this is an entertaining book.

This book gave me a deeper appreciation of how moral intuitions shape political divisions—not as accidents of ideology but as features of human psychology. Haidt’s metaphor of the elephant and the rider helped me see why rational argument so often fails to persuade across political lines: because reason follows intuition, not the other way around.

His mapping of multiple “moral taste buds”—including authority, loyalty, and sanctity—also challenged the narrow moral frameworks that dominate secular discourse. While I don’t agree with everything—particularly his optimistic lean toward moral equilibrium or his underemphasis on structural power—I admire his effort to move us beyond outrage toward curiosity. It’s a valuable guide for understanding why we talk past one another—and how we might start listening instead.

While most Americans make charitable gifts every year, people don’t give at uniform rates—there are vast differences by faith, family structure, political views, geography, and business involvement. For instance, people who worship every week give away three times as much money as those who rarely or never worship, and religious people are twice as likely to volunteer (for secular as well as faith-based causes).

Brooks shows that generosity isn’t just healthy for the nation; it makes the givers happier as well. He cites a host of social science studies demonstrating that charitable Americans are much more likely to be satisfied with life than non-givers who are demographically identical.

Bogle’s philosophy is simple yet powerful: focus on the long term, keep costs low, and let compounding do the heavy lifting. I’ve always believed that great investing is about avoiding unnecessary risks and staying disciplined, and Bogle’s book distills that wisdom better than anyone else.

While I take a different approach than pure indexing, his principles of cost efficiency and long-term thinking are universal. Every investor—whether a stock picker or a passive indexer—should read this book at least once.

Why a book about investment in a list about trading? Many experience unaffordable losses trying to become day traders. Anyone thinking about becoming a trader should first understand the fundamentals of investment and whether they might be a better investor than a trader.

First, written in 1949, the advice in this classic work has stood the test of time. This edition has an introduction from one of the most successful investors of our times (Warren Buffet) and a commentary bringing it up to date from Wall Street journalist Jason Zweig.

Above all, I love this book because it avoids flashy but misleading get-rich-quick narratives and focuses on how to invest in the creation of value. And if you do decide to be a trader, this book will teach you a great deal too.