Criteria for The Most Enjoyable Investment Books of All Time are: (1) they should be gripping reading; (2) they should be superbly written; (3) if appropriate they should be really funny; and most of all, (4) they should enhance your professional knowlege without making you feel you're working. Here's the list:
Roger Lowenstein's books stand out because they are so thoroughly researched and well-written. Best of all, they read like thrillers. While his books are fun, they also contain insights and lessons that are highly useful for portfolio managers. Buffett is his analytical portfrait of Warren Buffett; When Genius Failed is his account of the collapse of Long-Term Capital Management. If you're going to read only one book on this list, go for When Genius Failed.
Andy Kessler's terrific account of his time as a sell-side analyst covering semiconductor stocks for Morgan Stanley is called Wall Street Meat. It's hilarious, insightful, and contains wonderful portraits of people who are still players today. Take this on a plane journey and you'll finish it before you land.
Andrew Tobias is smart, experienced, and extremely funny. My Vast Fortune is a catalog of his mistakes and successes, as well as a exposure to the way he thinks about money. His personal finance book, The Only Investment Guide You'll Ever Need, is an insightful and hilarious read for investment professionals, and also makes a great gift for people looking for basic investment advice.
Michael Lewis describes four years with Salmon Brothers, and the events from 1984 through the crash of October 1987 in Liar's Poker. Don't expect many insights into how the Street works today; do expect a gripping and enjoyable read.
James Stewart's Den of Thieves is an account of the junk-bond insider trading scandal, and the people who pulled it off - Milken, Boesky, Siegel and Levine. Like many "scandal" books, it fails to recognize the importance and benefits of innovative financial instruments; but it makes great reading.
Interviews with investors and traders often make fun, enjoyable and thought-provoking reading, and a more stimulating way to think about investment methodology than reading heavier books. The best collections of interviews capture the uniqueness of the person being interviewed and highlight the key lessons for other fund managers. There are three good books to buy here: Investment Gurus by Peter Tanous, and two books by Jack Schwager: Stock Market Wizards and The New Market Wizards.
If you have nominations of your own for The Most Enjoyable Investment Books of All Time (not necessarily the best investment books, just the most enjoyable), leave a comment below.
Here are links to the books suggested by readers:
K Gala nominated Education of a Speculator and Practical Speculation, both by Victor Niederhoffer.
R Lubman nominated The Money Game by Adam Smith and Reminiscences of a Stock Operator by Edwin LeFevre.
Lou nominated F.I.A.S.C.O and Infectious Greed by Frank Partnoy.