The cracked.com podcast, specifically the episodes with Jason Pargin were God-tier.

I can't see a world in which I would re-listen to the archive, but they were foundational to so much of my thinking. And to this day I follow Pargin on whatever podcast episode he goes on, and on any subject, knowing it'll be incredible.

If you somehow haven't heard, the Secretly Incredibly Fascinating Podcast has him as a regular guest: https://sifpod.podbean.com/

As does 1-900-HOTDOG - https://soundcloud.com/1900hotdog

Each of these are by former Cracked employees, so when Jason Pargin is on, the conversation gravitates to a lot of the same big subjects - society, art, culture, science, and all the ways in which we take it for granted, or don't understand nearly the way we should.