The Gauntlet's Fear of a Black Dragon takes a look at (mostly) TSR-era and OSR adventures, analyzes how they play, and then pivots to deeper discussion on GMing a particular facet of that adventure.
My vote would be for d20 Dames, a dnd5e actual play podcast. It's dmed, casted, and produced by a diverse group of women. It's super funny and super engaging.
www.d20dames.com
http://www.chimpions.co.uk great super hero actual play RPG fun .
Dungeons & Randomness - This is a fun group of people who have a good global community to of players from all over the world. They have been consistently playing D&D campaigns for some time. The most amazing thing about this pod cast has been listening to the transformation of the Dungeon Master's life. He started the pod cast as a factory worker who was always told that he shouldn't follow his ambitions, and through help with the community he transformed his life so that he was able to do this pod cast and make a living by doing it! He even eventually meets his wife. The blend of real and fantasy is truly inspiring in this epic podcast.