I’ve been asked by the parents of an enthusiastic 14 year old computer nut for some fun “ICT” reads. Resisting an urge to cry “oxymoron”, I morphed what sounded like a request to reinforce the current curriculum of government procurement writ large in today’s schools into a subversive introduction to old school free software and hacker culture:
Actually, I’m unhappy with the fifth choice so wondered about Eric S. Raymond’s The Cathedral and the Bazaar mainly for the How to be a Hacker essay, Fred Books‘ The Mythical Man Month as an entertaining glimpse into large scale computer development, chocked full of great adages such as There is no Silver Bullet, Paul Graham’s Hackers and Painters because it says, it’s OK to be a geek and encourages learning LISP, and the rather dense Beautiful Code, for once he’s actually smitten with programming.
So, dear LazyWeb, did I do wrong? What other gems did I miss?

[...] http://blog.whatfettle.com/2008/10/27/suggested-books-for-an-aspiring-hacker/ asks Hoosgot, [...]
Apropos codes, I really liked Leo Marks’ Silk and Cyanide; describing how a self taught code breaker worked with SOE in the Second World War - rather touching and deeply interesting.
The Pattern on the Stone: The Simple Ideas That Make Computers Work by W. Daniel Hillis
A very good list. I’d say Hackers and Painters is a sure bet, and would add Glyn Moody’s Rebel Code.
How about Godel, Escher and Bach?? Or would that be too out of track from a strictly ‘hacker’ perspective. That book has made me a more rigorous thinker, though I have not crossed chapter 4 as yet!
If you want to mix things up a bit I’d recommend “Little Brother” by Cory Doctorow.
While fiction, it is a great way to inspire young hackers. He can even get involved in the Paranoid Linux distribution that was inspired from the book: http://paranoidlinux.org/
You can see if Little Brother would be appropriate or just give him the link: http://craphound.com/littlebrother/download/
I quite liked Open Sources 2.0
I think A Pattern Language has its merits
The Programmer’s Stone is not bad
Interface Culture is to be considered in such a list
But the one I would really fight for is The Social Life of Information