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In time spent as a sell-side research analyst, managing long/short money and then building Seeking Alpha, I've read literally hundreds of investment books. These recommendations are all personal, so don't treat this as an objective list of what's best. If you think I've forgotten something, please leave a comment with your suggestion below. The links are to Amazon, where you can read more about the books:

MONEY MANAGERS' EXPERIENCES

  1. Confessions of a Street Addict by Jim Cramer. Jim Cramer's experience as a fund manager; best of all his books.
  2. Running Money by Andy Kessler. Running a tech hedge fund in the bubble.
  3. Wall Street Meat by Andy Kessler. Life as a sell-side research analyst.
  4. When Genius Failed by Roger Lowenstein. Gripping account of the failure of Long Term Capital Management.
  5. Beating the Street by Peter Lynch. Magellan Fund Manager's famous book on stock picking.
  6. John Neff on Investing by John Neff. Contains stock diary of the market-beating Windsor Fund.
  7. Market Wizards by Jack Schwager. Readable interviews with top traders and fund managers.
  8. The New Market Wizards by Jack Schwager. Schwager's follow-up; more generic, but still worthwhile.
  9. Julian Robertson by Daniel Strachman. Portrait of arguably the most influential hedge fund manager ever.

VALUE INVESTING

  1. The Essays of Warren Buffett by Warren Buffett. Excerpts of his writings arranged by topic.
  2. Security Analysis by Benjamin Graham. The reference book for all value investors.
  3. The Little Book That Beats the Market by Joel Greenblatt. Value investing handbook by successful money manager.
  4. Value Investing by Bruce Greenwald. Rigorous discussion of valuation metrics.
  5. The Essential Buffett by Robert Hagstrom. Outline of Buffett's views.
  6. Buffett by Roger Lowenstein. The best portrait of Buffett.
  7. Contrarian Investment Strategies by Marty Whitman. Famed value-oriented fund manager on his methodology.

SHORT SELLING

  1. Sold Short by Manuel Asensio. Experiences of the most famous short seller.
  2. The Art of Short Selling by Kathryn Staley. Case studies in short selling.

INDEXING AND MARKET EFFICIENCY

  1. The Great Mutual Fund Trap by Gregory Baer. Why you shouldn't buy mutual funds. Ever.
  2. On Investing by John Bogle. Essays by the guru of indexing.
  3. A Random Walk Down Wall Street by Burton Malkiel. The case for indexing and against stock picking.
  4. Searching for Alpha by Ben Warwick. The best discussion of market efficiency versus stock picking from an active manager.

INVESTMENT PSYCHOLOGY

  1. Why Smart People Make Big Money Mistakes by Gary Belsky. Behavioural economics applied to stock picking.
  2. Fooled by Randomness by Nassim Nicholas Taleb. How to spot the signal in the noise and invest accordingly.
  3. The Psychology of Finance by Lars Tvede. Understanding the market with psychology.

ASSET ALLOCATION

  1. The Intelligent Asset Allocator by William Bernstein. Asset allocation using index funds.
  2. Pioneering Portfolio Management by David Swenson. Asset allocation and valuation by the market-beating manager of the Yale Endowment.

TRADING STRATEGIES

  1. Trade Like Warren Buffett by James Altucher. Buffett as a trader, not an investor.
  2. The Hedge Fund Edge by Mark Boucher. Hedge fund strategies; serious but readable.

CONTRARIAN INVESTING

  1. The Triumph of Contrarian Investing by Ned Davis. How to measure investor sentiment.
  2. Contrarian Investment Strategies by David Dreman. Excellent outline of contrarian investing.

LONG TERM INVESTMENT STRATEGIES

  1. Investment Fables by Aswath Damodaran.Exposure of investment fallacies by respected academic; it's even highly readable.
  2. Tomorrow's Gold by Mark Faber. Slightly rambling argument for emerging market stocks.
  3. Common Stocks and Uncommon Profits by Philip Fisher. The case for long term investing in stocks.
  4. The Gorilla Game by Geoffrey Moore. The case for high-growth tech stocks.
  5. Bull's Eye Investing by John Mauldin. Hedge fund broker on long-short investing; poorly edited but interesting ideas.

OPTIONS

  1. Options as a Strategic Investment by Lawrence McMillan. The authoritative book on options valuation and investing.

FINANCIAL ANALYSIS & VALUATION

  1. The Financial Numbers Game by Charles Mulford.Careful examination of accounting tricks to look out for.
  2. Quality of Earnings by Thornton O'Glove. How much are companies really earning?
  3. Expectations Investing by Alfred Rapaport. Stock picking based on what's priced-in.
  4. Financial Shenanigans by Howard Schlit. Financial manipulations to look out for.
  5. Irrational Exuberance by Robert Shiller. Called the market top in the late 90s; methodology is still important.

TECHNICAL ANALYSIS

  1. Technical Analysis of Stock Trends by Robert Edwards. Probably the most popular book on technical analysis.
  2. How to Make Money in Stocks by William O'Neil. Combination of fundamental and technical analysis by founder of Investors Business Daily.
  3. Technical Analysis Explained by Martin Pring. Popular guide to technical analysis.

Note: All links are to Amazon.com. If you buy there, Seeking Alpha gets an affiliate fee without it raising the price to you.

Source: The Best Investing Books Of All Time