The 15 Greatest Computer Books of All Time

DOS for Dummies
DOS for Dummies

Author: Dan Gookin

Published: 1991

Still in print? Yes, amazingly. (I wonder how many copies a year it sells?)

Googleosity: 122,000,000 (for all "for Dummies" references-91,400 for "DOS for Dummies" ones alone)

Why it matters: In 1991, I attended a cocktail party at a computer trade show and met some folks from the book-publishing arm of my then-employer IDG. One of them told me about a beginners' guide to PCs it was about to release. "The title is kind of controversial around the office," he said. "It's DOS for Dummies."

The moniker worked. IDG started cranking out Dummies volumes-computer-related ones at first, and then everything from cars to food to sex. Nearly twenty years later, over 1700 Dummies books have been published by IDG and Wiley, the publishing giant that bought IDG's book division in 2001. You could pretty much live your entire life based on the series. And it inspired both countless TV and movie references and multiple shameless imitators, such as the loathsome Complete Idiot books.

DOS for Dummies (which eventually sold more than a million copies) was written by Dan Gookin and illustrated with cartoons by Rich Tennant. The loose, funny personality was definitely Gookin's-I edited articles he wrote in the pre-Dummies era so I knew his style. It's mimicked in Dummies books of all sorts until this day, and Gookin probably deserves a nickel royalty for every tome ever sold. (He's still writing new Dummies volumes-here's his Droid X one-and Tennant cartoons are still a trademark of the series.)

Accidental Empires
Accidental Empires

Author: Robert X. Cringely

Published: 1992

Still in print? Yes, and you can sample it on Google Books

Googleosity: 33,400

Why it matters: Today, for bizarre reasons, there are two writers who toil pseudonymously as Robert X. Cringely-one who works for InfoWorld and one who doesn't. Accidental Empires was written back when there was only one Cringely-the one who doesn't write for InfoWorld. Except that at the time, he did. (Confused yet?)

Steven Levy's Hackers was a book about people Levy admired-at least in some respects-written before very many of them had made vast sums of money. (Microsoft hadn't even gone public yet.) Accidental Empires covers some of the same ground. But by the time it came along, computers had become a far bigger business. Cringely, InfoWorld's gossip columnist, is snarky where Levy was sincere, and treats his subjects as tycoons as much as nerds. And even though his analysis isn't flawless-"Alas, I'm not giving very good odds that Steve Jobs will be the leader of the next generation of personal computing"-it's an entertaining, insightful snapshot of the industry stood at the time. (The early-1990s vibe is strong: Cringely compares Bill Gates to the Emir of Kuwait, and Steve Jobs to Saddam Hussein.)

In 1996, the book was adapted into an even better PBS documentary miniseries, Triumph of the Nerds (which is still available on DVD and is online in transcript form). The TV version was made back when it was possible to convince both Bill Gates and Steve Jobs to sit for interviews for a TV program about the history of PCs, and is rife with great sound bites-including this gem.

The Road Ahead

The Road Ahead

Author: Bill Gates

Published: 1995

Still in print? No, but I saw a new (albeit marked-down) copy of the paperback edition for sale at one of my favorite bookstores just this weekend

Googleosity: 398,000

Why it matters: In 1975, Harvard student Bill Gates and his buddy Paul Allen saw that computers would eventually be everywhere and it would be a good idea to start a company to make software for them. That alone was foresight enough to establish Gates as one of the all-time great tech visionaries. Which is good, because his later, more formal attempts at predicting tomorrow's technology have been spotty at best.

Gates' most extended work of futurism was his book The Road Ahead, co-written with Microsoft research head (and future alleged patent troll) Nathan Myhrvold and journalist/technologist Peter Rinearson, and published at a time when Gates was still in the process of becoming a household name. Helped by a $1 million marketing budget, an Annie Liebovitz cover, and a booming interest among Americans in something vaguely known as "the information highway," it was a bestseller. Fifteen years later, it's an interesting read, in part because Gates' broad ideas about where tech was going were often right, but the more specific he got, the more he was hobbled by an understandable tendency to see everything as a PC. (He devotes several pages to something he calls the "Wallet PC," which-except for the fact it isn't a phone-sounds an awful lot like an iPhone.)

Gates repeatedly downplays his prowess as as predictor of trends in Road, and it wasn't just modesty: The first edition of the book also downplayed the Internet, just as the Internet was becoming the next big thing. He explained, in fact, that the Information Highway was going to be something else entirely. The moment the book came off the presses in late 1995, it was obvious that was a bad call. A heavily-revised 1996 edition emphasized the Net, at the same time Microsoft was doing battle with Netscape for the hearts and minds of browser users; a 1999 follow-up, Business @ the Speed of Thought , was even more cyberspace-centric.

The Road Ahead came with a CD-ROM that included, among other things, a video tour of the Gates family's megahome and a copy of a then-current piece of software called Internet Explorer 1.0. I'd love to express an opinion about it, but my copy of the disc (which I didn't opened until I began work on this article) won't run on Windows 7. (Apparently, it was glitchy even when you used it with Windows 95.)

The book, of course, still works great. There's a lesson there.

The Cathedral and the Bazaar
The Cathedral and the Bazaar

Author: Eric S. Raymond

Published: 1999

Still in print? Yes (and it's available in an evolving online version, too)

Googleosity: 60,900

Why it matters: In 1997, programmer and open-source software advocate Eric Raymond-the same guy who edited The New Hacker's Dictionary-gave an influential talk about contrasting approaches to open-source development at a Linux conference in Germany. It was titled "The Cathedral and the Bazaar" and became the title essay of a book published in 1999.

As defined by Raymond, the cathedral approach to open-source development keeps control of code in the hands of a small group of people. The bazaar approach most famously represented by Linux) allows a far larger, looser team of contributors to participate. The bazaar system has pretty conclusively won out in the years since Raymond spelled out the two systems, and his work played a significant part in its acceptance.

One concrete bit of proof of the importance of "The Cathedral and the Bazaar:" In 1998, Netscape CEO James Barksdale announced that the company was releasing the Netscape code as an open-source project called Mozilla-a move that eventually led to the creation of Firefox. Barksdale specifically credited Raymond's essay with inspiring the unprecedented decision.

...and that's my list of the great computer books. Did I leave out any? Definitely, and I know you'll point them out in the comments.

Here, I'll help get the debate going. Surely The Cluetrain Manifesto should be here, no? How about Ed Yourdon's Death March and/or Fred Brooks' The Mythical Man Month? Maybe Adam Osborne's Introduction to Microprocessors or Tsutomo Shimomura and John Markoff's Takedown or (thinking about recent works) Scott Rosenberg's Dreaming in Code ? Nominate your favorites; I'd love to do a sequel to this story.

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