This documentary by the Discovery Channel was done back in 2001 with John Draper AKA Captain Crunch, Steve "Woz" Wozniak, Mitnick and more. There is no longer a section for it on their site, but you can find this pretty much anywhere. So here's a link to see the whole thing for free:
http://video.google.com/videoplay?docid ... of+hacking
There are plenty of good documentaries on hacking and the computer industry. Guess I'll have to plow through the old AVIs and start posting them.