Down the Rabbit Hole for EVE Online is absolutely amazing. I've played the game here and there for quite a long time, and it's one of my favourite experiences, that is however really hard to put into words.
That game is weird. I still can't explain why it's one of the best games I've played, but I always keep returning to it and love consuming content about it from time to time. And this document is amazing in explaining how extremely unique and cool the game is in it's metagame and the stories it generates. The game has it's problems, but I still think it's one of the most unique lifestyles in gaming, that nothing ever comes close to. It's the only MMORPG that's actually literally roleplay, that basically forces you to roleplay without you even realizing it. Sure, you may not speak in character, but the fleet doctrines, logistics, corp organization, propaganda, corp-politics and everything around it people do - that's literally roleplaying.
Another one would be B-Movie: Lust & Sound in West-Berlin 1979-1989. This document is really really hard for me to watch, because it's a subculture that was always really important to me, to the point where I help with event promotions and DJ at local 80s goth/synthpop events and it's my main hobby. But, since I'm now in my 20s, I've missed it. The way internet transformed music subcultures is terrible, especially so the alternative ones, but music consumption in general - sure, it's really amazing to have every almbum ever in the palm of your hand, but there's just so many that I don't know any. If I talk to anyone who started with music with the one MC tape, and each new relleas was something hard to get that you actually treassured, I really envy their relationship with music. And that's something that's almost impossible to build in this day and age.
The fact that I'll never get to experience the scene as it was in the 80s is one of the saddest things for me, and this documentary shows it in really genuine and amazing way.
And then there's The Social Dillema, about the dangers of social networks. A word of warning from people who worked at large social network companies and left because the way they exploit users got too much for them, and now they are trying to spread the word. I really recommend this for everyone, it's eye openning and really terrifying. It was one of the first impulses that got me heavy into privacy, and it everyone should see it at least once.