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Michael David Madonick is my hero.
Waking the Deaf Dog
Michael David Madonick
My degree in nonfictional rhetoric isn't so much a product of my coursework as it is a side effect of my association with Michael David Madonick. He taught me many things, foremost among which are these:

Get used to throwing away almost every word you write; keep only the stuff that's really good. Also, Rebel Yell bourbon is about as good as you're going to find for under ten bucks a quart. Anyway, Waking the Deaf Dog is a volume of his poetry, and all I can really tell you is this: if you like my writing, then you should read the work of the man who taught me.

If Neal Stephenson wrote a book about pocket lint it'd still somehow involve a helicopter.
Interface
Stephen Bury (J. Frederick George and Neal Stephenson)
Yup, it's one of those "Successful genre author writes a book under a pen name and after he gains mainstream success everybody goes digging for everything he ever wrote and then the oddball book gets popular too" things. I'm still reading Interface, personally, so I can't say much yet, but I assure you: it's Stephenson.

Stephenson spent much of his young life in Champaign-Urbana, Illinois, which is where I went to college; now he lives in Seattle, where I've been for the past year. Part of Interface is set in one of Denver's nameless ghost-town suburbs. I spent a year near Denver. I have thuswise determined that Neal Stephenson's destiny is inextricably intertwined with my own. My life is simply one of the threads in an immensely complex parallel plot structure. I know now that when I die it will be on page 475 of a 478-page novel and it will be truly spectacular -- maybe a powerdive into the heart of a runaway fusion reaction on a jet-black speedbike/hovercraft while a hundred million viewers watch on in horrified elation as I slip into the nuclear bloom, destroying the deadly retrovirus, saving the world, and being a MASSIVELY FRAGTABULOUS BADASS in the process. Damn, I feel like doing some pushups.

Cryptonomicon
Neal Stephenson
I, like most sysadmins I know, ran straight to a terminal when I reached the part where eruditorum.org is mentioned. Alas, it was taken (by a friend of a friend of mine, oddly enough), so out of desperation I registered qwghlm.com before I realized I couldn't think of a damn thing to do with it. I think my epitaph should be "It was funny at the time". Anybody want qwghlm.com?
Snow Crash
Neal Stephenson
One of the undisputed classics of geek scifi. Essential reading for anyone who's ever secretly dreamed of being a badass.

The Diamond Age
Neal Stephenson
It's not my fault that Neal Stephenson dominates this list. He just rules too much to be eschewed.
Real life seems so boring now...
The Hobbit
J.R.R. Tolkien
Some books have such a deeply pervasive influence on our culture that their actual existence as a piece of literature becomes secondary to their existence as a source of references, like when I'm trying to trace a network problem on a server with lsof and I get to say, "Mmmm... what has it got in its socketses?" to whoever's unlucky enough to be nearby. If you like sacrilege, profanity, and toilet humor (who doesn't?) check out the Harvard Lampoon parody, Bored of the Rings.
Fool On The Hill
Matt Ruff
I can't comprehend how I could possibly have neglected to mention this book for so long. Fool On The Hill is one of the most wonderfullest books I have ever read in the roughly 9,060 days I've been alive. There's a fight scene (you'll know it when you get to it) which had me yelping in tiny excited gasps as I read. When I was done I read it again. Sorry for gushing, but this is the sort of book you feel compelled to evangelize for. It's textual espresso. Yow.
Sandman: Preludes and Nocturnes
Neil Gaiman
The first of Gaiman's Sandman collections. I feel foolish when I try to describe Neil Gaiman's work, so I'll refrain. I'll just say that I would trade my legs for his skills. If you've been curious about why people get so obsessed with Sandman comics, you really ought to just take the plunge: get this book and see for yourself. A note: this collection is widely acknowledged to be the runt of the litter. Knowing this makes it all the more fascinating to read; if this is the weak one, what are the rest like? Gaiman fans: have you read Signal to Noise? It's a beautiful and mildly brooding collaboration with Dave McKean . Signal to Noise is the sort of book you can keep on hand as a spiritual aperitif when your soul needs some shaking up. Alas, it's out of print now, but you can probably find it used. Then there's The Day I Swapped My Dad for 2 Goldfish, a slyly disturbing, masterfully absurd tale for the impressionable wee tyke in us all. (Credits: Melissa Binde for showing me Signal to Noise; Erica Erfman for lending me all her Sandman books.)
Neuromancer
William Gibson
The grandfather of Snow Crash. An entire genre of modern entertainment is essentially derivative of this book. It's required reading, and hey -- unlike Stephenson's epic tomes, you won't need to take a week off work to read it.
Ender's Game
Orson Scott Card
This is for anyone who felt as a child that being smart was a pain in the ass. If you've read Ender's Game, you should check out Ender's Shadow.

Catharsis is like sneezing, only not quite so moist.
Our Dumb Century
The Onion
I'd have to say my favorite Onion article is "P-Funk Mothership Accidentally Descends on Hootie Concert".

User Friendly
Illiad
The first collection of User Friendly comics. The best part is that it's published by O'Reilly.

Johnny the Homicidal Maniac
Jhonen Vasquez
I'm including this, not because it's actually well-known -- it isn't, really -- but because it's EXACTLY the sort of black humor that best typifies the dark side of geekdom. If you liked JTHM, you'll also like Squee's Wonderful Big Giant Book of Unspeakable Horrors and Sam & Max.

The Hitchhiker's Guide to the Galaxy
Douglas Adams
If I were trapped on a desert island, the one thing I would most like to have with me is this book. No, wait. That's stupid. I'd want an Iridium phone. But if I could have TWO things, I'd want... well, enough potable water to support me until help arrived. Okay, THREE things, I'd -- oh, screw it. I sat down to write a snappy little blurb on this sucker and ended up with an essay on the nature of geek humor.
Weird Memes and Strange Attractors
Memes are viral ideas: thought patterns which replicate by altering the carriers' minds in a way which compels them to spread the meme to others. The idea of memes is itself a meme, and a really cool one.

Strange attractors are well-defined forms generated by graphing the multiplicity of possible solutions to equations whose variables are all interrelated. They represent the chaotic nature of fundamentally unpredictable systems and the order that emerges if you just know where to look.

Godel, Escher, Bach: An Eternal Golden Braid
Douglas Hofstadter
This is the 20th anniversary edition of the book that made it just ever so slightly cool to be a math geek. My favorite part of the Amazon review is the summary of topics covered: J.S. Bach, M.C. Escher, Kurt Gödel: biographical information and work, artificial intelligence (AI) history and theories, strange loops and tangled hierarchies, formal and informal systems, number theory, form in mathematics, figure and ground, consistency, completeness, Euclidean and non-Euclidean geometry, recursive structures, theories of meaning, propositional calculus, typographical number theory, Zen and mathematics, levels of description and computers; theory of mind: neurons, minds and thoughts; undecidability; self-reference and self-representation; Turing test for machine intelligence. Hoo-ee! Them's some GOOOOD readin'!
Wicca : A Guide for the Solitary Practitioner
Scott Cunningham
Wicca has a strong following in the geek community, and it makes sense: the rituals of Wicca are like software with which you can query or alter the data structures and processes of the universe. Call it reality hacking. This book is often cited as a good Nutshell guide: a combination primer/manual/reference for both novice and expert.
Principia Discordia
Malaclypse the Younger
The essential introduction to Discordian thought. If you're been looking for a book to call your Bible, this might just be it.
The Illuminatus Trilogy
Robert Anton Wilson
The classic Discordian epic. The great thing about this book is that even if you don't like it, you'll be astounded at how many in-jokes suddenly make sense. If you already know and love this book, you should check out the further revelations of Robert Anton Wilson.
Some books don't have unicorns in them.
Microserfs
Douglas Coupland
This book is fun on a couple of levels: great postmodern-influenced fiction, yes, but if you live in Seattle or San Francisco you'll enjoy seeing your city as the backdrop (DUDE, you know that part where that guy goes to Uwajimaya in Redmond? That's like right by Paul's house!)

# find /home -regex '.*\(mp3\)\|.*MP3' -exec mv {} /scratch/.warez \;
Unix System Administrator's Handbook (3rd Ed.)
Nemeth et al.
One of the best ways I know to jumpstart yourself into Unix system administration is to read this book cover to cover, like a novel. How many technical books advise you to take a forty-ounce bottle of Pabst Blue Ribbon to the machine room?

Essential System Administration
Æleen Frisch
The Armadillo book. I cut my teeth on the first edition, and whenever I need a quick refresher on some aspect of Unix I'll usually look it up in this one. Æleen spells her name with a Æ, which is a capital AE ligature. This is extremely, deepy, pathologically geeky. I'd never even seen one before I got this book. I had to go check an HTML guide to find out how to produce one. Incidentally, if you aren't seeing the capital AE ligature, but instead are seeing a lowercase Z with a slash through it, then you are not using an ISO8859-1 compliant font and that is NOT MY PROBLEM. Such is the righteous tyranny of the hegemonic fonts! ISO8859-1 Über Alles!
UNIX Power Tools
Jerry D. Peek, Tim O'Reilly, Mike Loukides
This book rocks. It's like spending a year in an office with an experienced sysadmin. It even proselytizes at you about why you shouldn't write scripts in C shell. Reinforces the old saying that Unix is not so much an "Aha!" experience as it is an "Oh my god..." experience.
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