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Most of these are older, some are more slept on.
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.
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.
Synthetic Pleasures (1995) - I remember trying to find this movie back in the day and being unsuccessful. Super graphics and vintage flavor. One of my favorites.
Cyberpunk (1990) - William Gibson, Timothy Leary, and more! This is 1990s hip. A young Jaron Lanier makes an appearance.
Extras
No Maps For These Territories (1999) - William Gibson interviewed in a car and lots of millenium cybertech mood.
Mondo 2000 Flashbacks From The Future (2018) - R.U. Sirius interviewed. There is no Mondo 2000 documentary but there should be. Better yet a feature film.
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bornXslippy
awesome. Thanks for sharing.
Valis
Wow! Great list! I will check out some of these for sure!
Working on an addendum but couldn't really find many other films that fit as much. I like the early 90s vision of the net and technology and how it was thought these would impact culture. Almost in a retro-futuristic way. There are certain values and ideals from that era which are worth looking back upon.
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
TechnoCalyps (2006) - 3 hour long documentary about transhumanism. I need to watch this one again. I'm skipping through it and there's tons of people in here. Terence Mckenna, the Dalai Lama, etc.
https://www.youtube.com/watch?v=Thd8o47kep8
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
by Relish Ubiquitous; ; Report
I had 2 more written down:
Building Gods - Short documentary. This is sort of cyberpunk but more on the transhumanist/AI side of things. I think this came out in the mid 2000s.
https://www.youtube.com/watch?v=fbIwZjuLh00
Becoming Transhuman - Mark Pesce's spoken word documentary. I need to watch this again. It was for a Mindstates conference back in 2001.
https://www.youtube.com/watch?v=_PNHnxnIOHE
by Relish Ubiquitous; ; Report
Hyperland (1990) - Interviews with Ted Nelson, creator of hypertext and others. Presents the future World Wide Web, it's capabilities for learning about the world, and also interestingly predicts the development of algorithms for presenting content to the user. Multimedia as a concept is also presented, which would seem weird to have to explain in 2022, but this was all new in 1990. Features a pretty cool early VR demo also.
https://archive.org/details/DouglasAdams-Hyperland
by Relish Ubiquitous; ; Report