Revolution OS is a 2001 documentary which traces the history of GNU, Linux, and the open source and free software movements. I like Richard Stallmann.
Also consider watching The Social Network for some geek fun about the creation of Facebook. (Thanks to Umut for these two)
Discovery Channel - The History Of Hacking
History of Video Games
Guns Germs and Steel
Blackadder - Final episode
Code Rush (Netscape Mozilla Documentary 1998 - 2000)
ps: I was surprised to learn that Sourceforge was VA Linux before.
* Juanes - A Dios Le Pido
* The Sisters of Mercy - Ribbons
* The Sisters of Mercy - This Corrosion
* Duran Duran - Wild Boys
* Nine Inch Nails - Just Like You Imagined