Aardvark'd: Twelve weeks with Geeks (watch free online)
Four interns are brought into Fog Creek Software's Manhattan office and given 12 weeks to design, develop, debug and ship a computer program that will, among other things, help millions of frustrated users fix their relatives computers via the internet. Boondoggle Films presents a journey through the world of software development from the perspective of a unique software startup, four quirky interns, and the world of the geek.
Make Better Software: 6 DVD Training Series (not free, really expensive)
For ten years, Joel Spolsky has been teaching millions of programmers how to make better software. Now, you can look inside his company and see how it's done. Boondoggle Films presents a behind the scenes tour of Fog Creek Software's development process, from recruiting new team members to releasing new products.
Watching Joel's precepts in action will help you learn the key to successful software: it's about building a team of smart people who get things done, and then getting out of their way.
Code Rush (watch free online)
Independent filmmakers followed the Mozilla team from March 1998 to April 1999, as they worked to open Netscape Communicator's source code to the world, in a last-ditch effort to save the company. The result is an amazing snapshot of computer history, capturing the people that worked on it, the first internal beta test, the moment Jamie Zawinski uploaded the first builds publicly, the launch party, the all-hands meeting announcing the AOL acquisition, and so much more. It aired on PBS nationally in March 2000, the same month as the beginning of the dot-com collapse.
Disclaimer: I work for the company that produced the first two.