[CJefferson]

These are going to seem a bit strange, as they don't go that far into history, but I found the really interesting in showing how projects grow and evolve over time.

The Design and Evolution of C++ by Bjarne Stroustrup: This book is quite old itself now, but it talks about the early days of C++, and does a good job of describing how we ended up with the language we did.

The Old New Thing, Practical Development Throughout the Evolution of Windows by Raymond Chen. You can also read lots of the parts of this book on Raymond's blog, of the same name. This book really gave me a lot more respect for Windows and Microsoft on a technical level, giving many small fun stories on how functionality evolves over time, and how sensible decisions cause pain 10 years later.