Michael S Judge hosts the podcast Death is Just Around the Corner and is usually about parapolitics, shady history, the formation of the post-WW2 "rules based international order" which he refers to as the Fourth Reich and really gets a lot of mileage out of fleshing out the links from the Third Reich to the OSS and early CIA, the JFK assassination and CIA as organized crime and how the Bay of Pigs plays into it, global opiate market and Vietnam War, etc. but he also sometimes just gets really into the weeds on some aspect of psychology or linguistics, or mythology, or some music or movie he loves and thinks says something interesting about another broader thing he's interested in. He touches on Pynchon (Gravity's Rainbow especially) a lot, David Bowie, Charlie Parker, Stanley Kubrick, Dom Delilo, all kinds of stuff.

When he gets on a tear about something, he's one of the most impressive speakers I've heard at being able to really expand and detail complicated history or dense theory off the top of his head in really erudite long soliloquies where he can nest like three asides that expand on a point into one long point he's making and keep my attention the entire time. I'd recommend his entire podcast highly. His guest spots on Trueanon and Chapo are good starting places, but I'd give a heads up for CWs for substance abuse and mental health stuff, he was addicted to opiates and drinking by his own admission for a lot of the earlier stuff and sounds noticeably fucked up on some of them, and has frequently discussed having OCD and horror stories of his interactions with mental healthcare and pharmaceuticals. There's a multi part series he did on kicking opiates that gets really uncomfortable but is really well done.

(sorry for the long reply, but he's one of my favorites and super underrated imo.)