There are some pretty good videos on hacking, startups and open-source culture. Here is a list of them that I have been collecting since long. You will definitely enjoy them.
Go watch The Social Network first, if you havent and then come back to this list :P
I will keep updating this list by any new I find. Drop me an email, or comment below if you want to add something to this list.
[link] The History of Hacking – Discovery Channel Documentary
[link] The Code Linux
[link] Hackers: Outlaws and Angels
[link] CodeRush – The Netscape Mozilla documentary
[link] Freedom Downtime – The story of Kevin Mitnick
[link] The Google Documentary
[suggested by Darren Teoh]
[link] Revolution OS
[link] The Code Breakers
[link] The Secret History of Silicon Valley – by Steve Blank
[link] Richard Stallman of Free Software Foundation
[link] Pirates of the Silicon Valley – a movie about Apple and Microsoft in their early days.