Caring For Mothers and Children, an obscure 2-part documentary looking at the GDR and how they set about towards achieving gender equality:
https://tankie.tube/w/dJHRFjS3yYjy3T8EXwPUhn
https://tankie.tube/w/u6XkjrMYW5yjqemf4b5ZtQ
It's less than 25 minutes altogether.
This next suggestion is not like something from the darkest, forgotten corners of YouTube kinda obscure but for a film that had a mainstream release I don't think it's very well known. It did receive a lot of critical acclaim:
It's a foreign language adult's stop-motion animation film that draws directly from the story of Colonia Dignidad in Chile.
If you haven't heard about Colonia Dignidad and you're interested, I can bring you up to speed on the backstory (there's benefits to watching it both with that foreknowledge and without it though.)
I found a YouTube link in your comment. Here are links to the same video on alternative frontends that protect your privacy:
A movie? Slacker - by Richard Linklatter
Something interesting?
The Empire Files : The US School That Trains Assassins short video about the School of the Americas in Fort Benning GA.
Maybe they’re not obscure enuff, I dunno
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Link 1:
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Obscura for you.
https://www.youtube.com/watch?v=kGnutyhfIL0
https://www.youtube.com/watch?v=X6oUz1v17Uo
https://www.youtube.com/watch?v=o0x9ymMQUg8
I found YouTube links in your comment. Here are links to the same videos on alternative frontends that protect your privacy:
Link 1:
Link 2:
Link 3: