Conversations With Tyler: he tends to ask some of the most creative and interesting questions. For a specific episode recommendation, I really enjoyed "Donald S. Lopez Jr. on Buddhism". He also has an older interview with Paul Graham (pg), but I don't think the questions were as deep or challenging.
Dwarkesh Patel: he gets extremely high quality guests and he doesn't just roll over completely when the guest makes a claim, at least he's willing to ask follow-up questions. His guest lectures with Sarah Paine are outstanding for helping to contextualize your understanding of the world order of the past 100 years from an American perspective.
Wookash Podcast: very technical and focused on more advanced programming topics. For specific episode suggestions I suggest the recent ones with Anton Mikhailov where they talk about ~~ECS~~ arrays of things.
Two's Complement: a podcast by the guy who made the Godbolt Compiler Explorer. It doesn't release very frequently but it provides interesting perspectives. Just
Ezra Klein Show: this is one of the guys that wrote the Abundance book, which I think was a much-needed message. Most recently he had an interview with Clark from Anthropic, but it's from a fairly normie / non-AI-obsessed perspective.
I have to rant about podcasts:
My biggest issue with most podcasts is that it often feels like there's very little effort put into preparing for the discussion and there's not many interesting follow-up questions. I think you can challenge people's claims in good faith to make for more interesting discussions. At least ask some reasonable follow-up questions when the guest makes outrageous claims! A lot of podcasts are just an advertising platform for people to talk about their new book; if you can listen to a guest give the same conversation with a different host then that's probably a sign that the questions are bad and shallow, so you shouldn't keep listening to that podcast.
One of the issues with asking deeper questions is that anything truly interesting or new will probably require having thought about the topic a lot ahead of time. Otherwise you just end up getting a very shallow answer because people can't usually think through complex topics on the fly so the best you can hope for is to get a pre-cached or partially computed answer. It would be great to have a podcast dedicated to exploring more challenging and underexplored questions which are shared with guests ahead of time so both parties can have time to think and explore. Most famous people just go on podcasts to play their "greatest hits" without saying anything substantially different or new.