I've shilled him in other threads, but I'm a big fan of
Pseudiom, a youtuber that really deserves a much larger audience.
He makes videos about all sorts of subjects, often very niche. Anything from the story behind the Big Iron song, to a classic historical Japanese movie starring Johnny Cash, to the many potential names the US could have had, to the Dead Internet Theory, to the weird Mexican DBZ lore, to the Vatican's top ten rock albums, to the online blood cult based on Naruto, to many, many more.
Another thing I like is
Jonkari P, a guy who makes these little skits out of movie or tv show clips through clever editing, 3D models, and really good masking.
My favorites are the "Top Gear in Skyrim/Fallout" ones, but there's a bunch.
Last thing I wanna mention is the webcomic
Kill Six Billion Demons. Not obscure by any means, but I really like it.