Triumph of the Nerds
If you haven't seen the Triumph of the Nerds series from PBS' Robert X. Cringely, check it out! It was made in 1996... but it is still fascinating for anyone who either lived through it or is interested in computer history.
Part 2 and 3 are in the full article.
You can download the videos from Google in .mp4 format as well... but I don't know how good the A/V sync is.
Hey, while I'm add it, I might as well include Pirates of Silicon Valley.