I'm not really a fan of any podcasts for exactly the reason that most of them end up just being a bunch of boring people laughing at their own jokes. Or doing really deep dives on tedious pop culture stuff. But one that hooked me long enough to get through over 100 episodes was called Pirate History Podcast. I don't know how to link to it in a podcast player, but i listened to most of it on YouTube:
https://www.youtube.com/c/ThePirateHistoryPodcast
He does jazz what we know from fact up a little bit to make the stories more exciting, but he always lets you know the parts that are more likely to be legend. And for me, at least, someone who knew very little about this era of history before listening, i found that i learned way more about monarchies, religion and colonization. It led me down a bunch of wiki holes too, learning about sailing boats and rigging and the slave trade and the birth of capitalism and modern democracy and other interesting stuff.
Recently i've been following this guy on YouTube who does hour-long Powerpoints about the economics and politics of war:
https://www.youtube.com/channel/UCC3ehuUksTyQ7bbjGntmx3Q He was a computer game YouTuber till he did a serious post about the Ukraine war and suddenly blew up for creating a niche where he does dry and analytical takes on macro-level military thought. It's not really a podcast, i suppose, but you can get most of the information without looking at the slides. It's taught me a lot about how people in government think about the military, and the high level strategy of how armies are equipped and what purpose they serve in the modern world.
I think i prefer these kinds of things which are more one person giving a lecture on topics i know little about but still impact aspects of my life or our society today over a bunch of friends' banter. If i want to hear a bunch of unfunny dudes sounding off with there boring opinions i can just go to any bar anywhere in the world, you know?