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Shoot I have a LOT. Documentaries and educational youtube channels are my JAM. If people like my top picks here and want more recs, let me know and I will spill out my list of followed channels.
But the top ones that spring to mind:
Most of Barely Sociable's work (especially the two parter on bitcoin) but of all of his, my absolute favorite is The Dark Side of the Silk Road.
Again, most of Lemmino's works, but particularly Cicada 3301: An Internet Mystery
and honorable mention to Summoning Salt for The Quest to Beat Matt Turk a documentary about the history of Mike Tyson's Punchout speed running.