Joe Rogan Experience - Lots of very interesting guests, though I outright ignore any of the MMA features. Duncan Trussel and Joey Diaz are my two favorite guests. Stuff You Should Know - Wide variety of topics, explained in a super digestible way. In the same podcast family as Stuff You Missed In History Class. Kevin Smith's Smodcast for silliness and sometimes motivation. I don't like all of his films, but I really dig the dudes philosophy. Common Sense and Hardcore History from Dan Carlin - Dan just rocks, in a very general manner. Wrath of the Khans is possibly one of the best pieces of spoken word literature that exists. I listen to a lot of others, non as regularly as those four.*
You might like WTF with Marc Maron. Obama, Conan, Rogan and Joey Diaz were some of my favorites. Maron takes some getting used to but his conversations get really interesting.