In no particular order, I listen to all of them regularly:
-
Omnibus - general obscure history hosted by indie rocker John Roderick and Jeopardy's golden boy Ken Jennings
-
The Dollop - (mostly) American history with a leftist bent. One comedian reads a story the other hasn't heard before.
-
Not Another D&D Podcast - apologies for the first episode, but great world- and character-building. Really shows how great cooperative storytelling can be
-
Last Podcast on the Left - comedy/horror. Conspiracies, cults, UFOs, and other weird shit. Their historical deep dives are awesome.
I listen to these regularly, but there's a limited series podcast I like to recommend called S-Town. It's excellent, especially if you're from the southern US or grew up in a rural area. If you aren't from the south or a rural area, it'll probably be an extra-wild ride!