- Robert X. Cringely's book "Accidential Empires" is definitely dated but you can read most of the chapters on his blog here: http://www.cringely.com/tag/accidental-empires/
- Cringely also did a three part special back in the 90s that I like revisiting every once in a while. Again, pretty dated but entertaining nevertheless: https://www.youtube.com/watch?v=HuBXbvl1Sg4
- Skip the newer Steve Jobs movies and watch the history of Apple and Microsoft with Pirates of Silicon Valley. It's said to be mostly accurate: http://www.veoh.com/watch/v46093745wbEGkakh
- Kind of random but if you want a look back at what the 90s tech bubble was like then watch Startup.com: https://www.youtube.com/watch?v=ibuiUXOTE4M