I don't read a lot of "business books". I find most of them are simply rehashing and repackaging concepts that have been discussed before, or are trying to sell books based on a new buzz phrase ("viral marketing", "guerilla marketing", "paradigm shift", the list is endless). For this reason you will find that my picks lean towards stories about business rather than theoretical or "how to" business books. And I don't include "self help" or motivational books in my picks (Think and Grow Rich, for example, is on a lot of lists).
So my list of "best" business books isn't drawing from a very deep pool and are skewed towards historical story telling, so feedback in the comments if I sorely missed something you like. Note that many of the books on my list were required reading in business school so they may seem a bit dated:
1. The Prize - An outstanding read on the history of the oil business, plus lots of geopolitical discussion (would Japan have won the War in the Pacific if they hadn't missed the oil depot during Pearl Harbor?). Anyone even remotely connected or interested in this industry, or is interested in how oil has shaped and is still shaping world affairs should read this book (there was a PBS series based on this book which was "okay")I notice that I don't have Drucker and a few others, so there is a lot "required" reading that I didn't put on this list. In addition I didn't include Wealth of Nations and a few other economic texts since I don't consider them "business" books, as well as a few books sitting on my shelf that are pretty helpful (books on negotiating, doing business in Japan, etc.).
2. Liar's Poker - See the dirty side of the bond industry from a jaded, cynical point of view that gives lots of laughs. This was probably one of the most interesting reads I have had in all the classes I have taken. Unfortunately Michael Lewis's later book The New New Thing - about Silicon Valley - was a bit dry.
3. Barbarians at the Gate - Dramatic story of the RJR Nabisco LBO (leveraged buyout for you non-business types). I picked this up again a few years ago and find that it is getting a little dated, but it is still an eye opener on corporate excess, greed and the art of the deal (I hated Ross Johnson after reading this book, although James Gardner made him sympathetic in the HBO movie).
4.Competitive Strategy - The top theoretical book on my list and the basis from which I draw for nearly all my marketing analyses. If you want to do strategic marketing, this is your Bible.
5. Something by Tom Peters - Yeah, I know there are a lot of Tom Peters fans out there, and reading him does pump you up, but if you read one of his books, you pretty much have read them all. I read In Search of Excellence, Thriving on Chaos, and a few others, so just go find the one with the most recent publication date and you'll be okay.
6. The Goal - This is one of those books you read, think "whatever", and move on, but then find yourself thinking about it as certain operational business situations come up.
7. Rites of Passage - Maybe shouldn't be classified as a "business book", but as a "career book". I referred to it before while discussing Headhunters. It has lots of good information for managing your career and dealing with recruiters.
8. Extraordinary Popular Delusions and the Madness of Crowds - You think the Internet Bubble was unique? There was Tulipmania nearly 200 years ago, the South Sea Bubble and dozens of previous instances where speculation drove up assets far beyond what they were worth before crashing down and reeking financial havoc on countries and people. I read this a good 6 years before the internet bubble, and while I was more cautious than many, I still managed to get somewhat singed at the end..
Now for a few business books that will never make my "best" list:
1. Who Moved My Cheese - I spent 10 minutes reading this in a book store (yes, the entire thing) and thought "If this is the best selling business book in America, it's no wonder that over half of new businesses fail." At least I didn't pay anything to read it.
2. Seven Habits - This is a whole cottage industry: Seven Habit of Effective People, Seven Habits of Effective Families, Seven Habits for Teens, you name it. But let's face it, if you want to read this book and don't already have a work ethic in place, you need a lot more help than a book can provide.
3. Anything by Gates - Bold statements of the obvious told in a way that will induce slumber.
4. My Years with General Motors - This is supposed to be one of the business "classics", and even though I find the automotive industry interesting, and admire Sloan as a business person, I found this book unbelievably boring. It figures that it is one of Gate's favorites (it has five stars from eight reviewers at Amazon, so note that I am not in the majority on this one).