I think the vast majority of everything there is to know about investing is contained in a relative handful of books and articles written by just a few people. The big ideas don’t change even if the circumstances do.
This list is arbitrary by definition because it’s based solely on my opinion. It’s sorted alphabetically because they’re all excellent and there’s no sense in splitting hairs. There are also dozens of good books and articles that could have made the list, but I had to stop somewhere. My point is that if you read everything on this list, you would have covered almost everything important that there is to know about investing.
My expanded list, running some 220 items and counting, is sorted into tiers and can be found here. Suggestions are always welcome.
Bernstein, Peter L. Against the Gods: The Remarkable Story of Risk. New York: Wiley, 1998.
Bevelin, Peter. Seeking Wisdom: From Darwin to Munger. 3rd ed. Sweden: PCA Publications, 2007.
Browne, Christopher. "Value Investing and Behavioral Finance." Presentation to Columbia Business School. New York, New York. 15 Oct. 2000.
Buffett, Warren. The Essays of Warren Buffett: Lessons for Corporate America. Ed. Lawrence A. Cunningham. New York: The Cunningham Group, 2001.
Buffett, Warren. "Berkshire Hathaway, Inc. Shareholder Letters, 1977-2010." BERKSHIRE HATHAWAY INC. <http://www.berkshirehathaway.com>.
Buffett, Warren. "Buffett Partnership Letters." 1959-1969. <www.ticonline.com/buffett.partner.letters.html>.
Buffett, Warren. "The Superinvestors of Graham-and-Doddsville." Hermes: The Columbia Business School Magazine Fall 1984: 4-15.
Cialdini, Robert B. Influence: The Psychology of Persuasion. Revised Ed. New York: Harper, 2006.
Fisher, Philip A. Common Stocks and Uncommon Profits. New York: Wiley & Sons, 1996, and Fisher, Philip A. Conservative Investors Sleep Well. New York: Wiley & Sons, 1996.
Graham, Benjamin, and David L. Dodd. Security Analysis: Principles and Technique. 2nd ed. New York: Whittlesey House, McGraw-Hill., 1940, and Graham, Benjamin, and David L. Dodd. Security Analysis: Principles and Technique. 6th ed. New York: McGraw-Hill, 2009. "
Graham, Benjamin. The Intelligent Investor: A Book of Practical Counsel. 4th Revised ed. New York: Harper & Row, 1973.
Greenblatt, Joel. You Can Be a Stock Market Genius: Uncover the Secret Hiding Places of Stock Market Profits. New York: Simon & Schuster, 1999.
Hagstrom, Robert G. Investing: The Last Liberal Art. New York: Texere, 2000, and Hagstrom, Robert G. Latticework: The New Investing. New York: Texere, 2000.
Hagstrom, Robert G. The Detective and the Investor: Uncovering Investment Techniques from the Legendary Sleuths. New York: Texere, 2004.
Hagstrom, Robert G. The Warren Buffett Portfolio: Mastering the Power of the Focus Investment Strategy. New York: Wiley, 1999.
Hagstrom, Robert G. The Warren Buffett Way. 2nd ed. Hoboken, NJ: John Wiley, 2005.
Kahneman, Daniel. Thinking, Fast and Slow. New York: Farrar, Strauss and Giroux, 2011.
Klarman, Seth A. Margin of Safety: Risk-Averse Value Investing Strategies for the Thoughtful Investor. New York: Harper Business, 1991.
Loomis, Carol. Tap Dancing to Work: Warren Buffett on Practically Everything, 1966-2012. New York: Portfolio, 2012.
Lowe, Janet. Damn Right! Behind the Scenes with Berkshire Hathaway Billionaire Charlie Munger. New York: John Wiley, 2000.
Lowenstein, Roger. Buffett: The Making of an American Capitalist. 1st ed. New York: Random House, 1996.
Lowenstein, Roger. When Genius Failed: The Rise and Fall of Long-Term Capital Management. New York: Random House, 2001.
Marks, Howard. “Oaktree Memos from Our Chairman." Oaktree Capital Management, L.P. 1990-2011. <http://oaktreecapital.com/memo.aspx>.
Marks, Howard. The Most Important Thing: Uncommon Sense for the Thoughtful Investor. New York: Columbia University Press, 2011, and Marks, Howard. The Most Important Thing Illuminated: Uncommon Sense for the Thoughtful Investor. New York: Columbia University Press, 2013.
Montier, James. Value Investing: Tools and Techniques for Intelligent Investment. West Sussex: Wiley, 2009.
Munger, Charles T. Poor Charlie's Almanack: The Wit and Wisdom of Charles T. Munger. Ed. Peter D. Kaufman. Virginia Beach: Donning Co., 2005.
Risso-Gill, Christopher. There's Always Something to Do: The Peter Cundill Investment Approach. Montréal: McGill-Queen's U. Press, 2011.
Schroeder, Alice. The Snowball: Warren Buffett and the Business of Life. New York: Bantam Books, 2008.
Taleb, Nassim Nicholas. Fooled by Randomness: The Hidden Role of Chance in Life and in the Markets. New York: Norton, 2001.
Thorndike, William Jr. The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success. Boston: Harvard Business Review Press, 2012.
Tweedy, Browne & Co. “What Has Worked in Investing.” New York, Tweedy, Browne & Co.: 1992.
I have learned an enormous amount from these people and I highly recommend them and their work.