Nerdy Documentaries

Triumph of the Nerds  - Mid '90s documentary about the computer industry.

BBS:  The Documentary - BBS was the pre world wide web, a glimpse of what was to come. https://archive.org/details/BBS.The.Documentary/BBS.The.Documentary.ep1.avi

UNIX: Making Computers Easier To Use - Vibe with some AT&T gems, featuring Dennis Ritchie et al.  There's another one called "Making Computers More Productive." UNIX is explained very well in these.  

Freedom Downtime - Documentary about Kevin Mitnick and the crazy stuff he went through being an OG hacker.

Pirates of Silicon Valley - There's like 5 movies they made about Steve Jobs but the best in my opinion is the made for TV movie in 1999.

Revolution OS (2001) - Open source development people are interviewed. I think this is the more well-known Linux documentary. Captures a lot of early history.
https://www.youtube.com/watch?v=jw8K460vx1c

The Code (2001) - I had never seen this and confused it with Revolution OS. It's sort of the same premise.
https://www.youtube.com/watch?v=zPt_e9Cdk08

Hackers: Wizards of the Electronic Age (1985) - This is really OG. Lots of stuff in this short documentary.
https://www.youtube.com/watch?v=zOP1LNr70aU

NYC Hackers (2000) - Short documentary made for a visual anthropology project. Covers 2600 and the DeCSS code, media fears, civil liberties, MIT model train origins of hacking etc.
https://www.youtube.com/watch?v=2nxZe49mhS0