Since searching wikipedia turned up the Timeline of Non-Sexual Social Nudity(TIL) I'm just going to guess you're you're looking for a more techie true to life rendition of the hacker archetype based on the amazon synopsis.
These are told in a chapter/viewpoint style, each chapter is usually written by a different knowledgeable, and sometimes security famous, security dude. Out of those I've only read How to Own an Identity so far, but it was pretty good and and my guess is that the rest hold up to that standard, so dive in. They are a series from what I understand so reading them in order is probably a good idea, but not completely necessary.
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And then for flair (these are more scifi/cyberpunk-ish; so if that's not your thing avoid):
The main character's name is Hiro Protagonist. No seriously. He's a ninja, he's a hacker, he lives in a U-Store-it container, and he delivers pizza for the Mob in a post-collapse USA, can you really not read this book now?
All about the practical social implications of nanotechnolgy told through the eyes of a young girl, her father, and an assortment of disposable associates.
Cryptonomicon by Neal Stephenson if you like technology. As someone who usually reads non-fiction, I found it appealing and engaging, and the book will definitely get you through your flights there and back.
After I powered through the first 100-200 pages I couldn't put it down (This is not sarcasm) It made me realize some (Cant think of the word here... Amazing? Earth Shattering? Life altering?, meh) things! Such as there is no "chance". For example we say the flip of the coin in a chance thing, but it isn't, if you could replicate all the variables (how hard you hit the coin, the angle at which you hit the coin etc.) the coin would land on the same side every time.
It's long too! I think it was at 1000 pages? It had me reading a good two weeks before I finished it... That was in a third world country where I had nothing to do BUT read.
I never liked Snow Crash much although not as bad as the Baroque cycle. Of all Stephenson's books: Anathem and Diamond Age are excellent and Cryptonomicon and The Cobweb are very good.
Well, we hit the 10000 limit. Reserving this comment for the misc. section.
FREE TIME/FUN/MISC.
The Art of Deception: Controlling the Human Element of Security
The Art of War
Steal This Computer Book 4.0: What They Won't Tell You about the Internet
How to Disappear: Erase Your Digital Footprint, Leave False Trails, and Vanish without a Trace
The Best of 2600: A Hacker Odyssey
Super Crunchers: Why Thinking-by-Numbers Is the New Way to Be Smart
Casting the Net: From ARPANET to INTERNET and Beyond thanks sjhill
A Quarter Century of UNIX thanks sjhill
A Reading List For the Self-Taught Computer Scientist thanks zinver
How to Talk So Kids Will Listen & Listen So Kids Will Talk thanks segamix
The Black Swan: The Impact of the Highly Improbable thanks AgonistAgent
Snow Crash thanks AgonistAgent
Cryptonomicon thanks Mirple
Cryptonomicon - ciphers, startups, WW2 references and haiku writing marines.
Cryptonomicon, assuming he hasn't read it already. It should be right up his alley.
Since searching wikipedia turned up the Timeline of Non-Sexual Social Nudity(TIL) I'm just going to guess you're you're looking for a more techie true to life rendition of the hacker archetype based on the amazon synopsis.
Based on that I'd recommend:
Cryptonomicon
just.go.read.it.right.now.
It may take a little effort to get into, damn thing is a tomb, but give it a chance. You will not be disappoint.
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Stealing the Network Series
How to Own a Box
How to Own a Continent
How to Own an Identity
How to Own a Shadow
comments
These are told in a chapter/viewpoint style, each chapter is usually written by a different knowledgeable, and sometimes security famous, security dude. Out of those I've only read How to Own an Identity so far, but it was pretty good and and my guess is that the rest hold up to that standard, so dive in. They are a series from what I understand so reading them in order is probably a good idea, but not completely necessary.
_____
And then for flair (these are more scifi/cyberpunk-ish; so if that's not your thing avoid):
Snowcrash
comments
The main character's name is Hiro Protagonist. No seriously. He's a ninja, he's a hacker, he lives in a U-Store-it container, and he delivers pizza for the Mob in a post-collapse USA, can you really not read this book now?
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The Diamond Age
comments
All about the practical social implications of nanotechnolgy told through the eyes of a young girl, her father, and an assortment of disposable associates.
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The Sprawl Trilogy
Neuromancer
Count Zero
Mona Lisa Overdrive
comments
I've only read Neuromancer and Mona Lisa Overdrive, which were both great, so I'm guessing Count Zero is probably good too.
Similar to Snowcrash in the lone gun hacker sense, except with more drugs a little bit more of a scattered tone.
And if all else fails there's always the DEF CON reading list.
ninja edits because I suck at markdown
Cryptonomicon by Neal Stephenson if you like technology. As someone who usually reads non-fiction, I found it appealing and engaging, and the book will definitely get you through your flights there and back.
Not horror, but this one is brilliant:
The Illuminatus! Trilogy: The Eye in the Pyramid, The Golden Apple, Leviathan.
Also very good: Cryptonomicon.
Cryptonomicon
After I powered through the first 100-200 pages I couldn't put it down (This is not sarcasm) It made me realize some (Cant think of the word here... Amazing? Earth Shattering? Life altering?, meh) things! Such as there is no "chance". For example we say the flip of the coin in a chance thing, but it isn't, if you could replicate all the variables (how hard you hit the coin, the angle at which you hit the coin etc.) the coin would land on the same side every time.
It's long too! I think it was at 1000 pages? It had me reading a good two weeks before I finished it... That was in a third world country where I had nothing to do BUT read.
http://www.amazon.com/Cryptonomicon-Neal-Stephenson/dp/0380973464
I never liked Snow Crash much although not as bad as the Baroque cycle. Of all Stephenson's books: Anathem and Diamond Age are excellent and Cryptonomicon and The Cobweb are very good.
Edit: grammar and links