One book frequently overlooked when it comes to computer and internet history is The Dream Machine. It tells the story of J.C.R. Licklider, who was a psychology and computer science professor, and a director at ARPA. He had the vision for the "Intergalactic Computer Network" which became the Internet, and either directed or came into contact with nearly every project that created fundamental computing technologies.
The recent book by Brian Kernighan, "UNIX: A History and a Memoir" [1], was a fascinating personal memoir about the birth of Unix as well as how things used to work at AT&T Bell Labs.
Where Wizards Stay Up Late: The Origins Of The Internet
The Idea Factory: Bell Labs and the Great Age of American Innovation
The Chip: How Two Americans Invented the Microchip and Launched a Revolution
That last one is a little dry, I still found it interesting. It's about Jack Kilby and Robert Noyce. It's currently available for sale for $1.99 on the Kindle.
I'd add Eccentric Orbits and Skunk Works, both of which are about other fields (satcom and aero, respectively), but have similar themes of innovation and its mother, necessity. (And mother-in-law, politics.)
Along those lines, a personal favorite is Empires of Light, covering the race for electrification and lighting. It critically includes the role of George Westinghouse, which a lot of books leave out (typically focusing more on Tesla & Edison instead).
Dealers of Lightning is an order of magnitude more interesting than any other book in the genre I've ever read (mainly because of Xerox PARC of course). But for 90's stuff, Chapman: "In Search of Stupidity: Over Twenty Years of High Tech Marketing Disasters" is fun and really good as well :)
Seconded! In search of stupidity is a huge amount of fun. It can be a little mean-spirited/bitter at times, but it felt like a "Computer Chronicles: After Dark" kinda thing.
