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:

1. Hackers - Steven Levy's nice potted history of hackerdom from the MIT Tech Model Railroad Club to the Homebrew Computer Club and the resulting Silicon Valley microcomputer game hackers. Also highly recommended is Crypto by the same author.
2. The Soul of a New Machine - Tracy Kidder's Pulitzer prize winning story of pressured development in the days of Minicomputers. Riveting, with some great insight into the motivations for hackers in the zone.
3. The Code Book - Simon Singh's not strictly computing, but a very drinkable technical history from steganography exemplified by Histaiaeus shaving the heads of his messengers, writing the message on his scalp, and then waiting for the hair to re-grow, to the mind-bending world of quantum computing and quantum cryptography all interspersed with some great puzzles. Totally inspiring!
4. The Cookoo's Egg - Clifford Stoll's personal tale of how being tasked with resolving a $0.75 accounting error led him to foiling a computer cracker using Berkeley's lab to break into military systems. He grows tomatoes and microwaves his tennis shoes in the process.
5. Best Software Writing - Joel Spolsky's nice collection of snappy contemporary essays, possibly more likely to date badly than many of the above.

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?