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Exemplary DM Podcast - ***** Simply the best rpg podcast out there. Timeless, genuinely funny, well produced, on topic (mostly), and bursting at the seams with great ideas for DMs and players alike. This is a podcast about playing tabletop games, not about any specific product releases, and as such it will be as relevant in five years as it is today. For the most part, it works for any gaming system, though they focus mostly on DnD. I love this podcast. They recently released their last episode of season two, and I hope that they will be able to continue in the future...though one of the hosts is moving, which makes this hard to guarantee.
Official DnD Podcast - ***** These are not frequently produced at this point (though there has recently been more activity following the release of dndnext), but there's a tremendous back catalog of episodes spanning the entire history of 4e. Many of these feature designers pitching their products, which can be interesting on their own. The best part, however, are the Penny Arcade actual play sessions. Most are DM'd by Chris Perkins, who is a phenomenal DM, and the characters include the guys from Penny Arcade as well as (starting in series 2) Wil Wheaton. Yes, that Wil Wheaton. They are super funny, and are a wonderful model of how DnD can be played. Really fun stuff.
Haste by Obsidian Portal - ***** Great current events in gaming podcast. They cover everything, from indie rpg's to kickstarter, but DnD gets a bit more attention than other systems in my experience. I love that it's fast, focused, and often has interesting guests. They also take questions from twitter and provide DMing tips and such. It is a vehicle for advertising Obsidian Portal, but these are genuine gamers behind that company so it is easy to overlook this...and they're not in your face about it.
Icosohedrophilia - ***** With the possible expection of the DnD podcast, this is the best live DnD action podcast that I've encountered. I tried to do with it like I did with Critical Hit (see below)--start from the first episode and move from there. Unfortunately, early episodes have pretty bad sound, which makes it very hard to keep track of all 7 PC's. I gave up on it this, but then later tried again by listening to "The Story Thus Far" episode and going from there. This is definitely the way to do it. More recent episodes have far better sound, this lets you enjoy the strengths of the podcast. Chris Heard is a terrific DM, with great mastery of the rules, and more importantly the ability to concisely and yet vividly tell a great story--both in and out of combat. The recent Kiss of the Spider Woman chapter was amazing fun, so perhaps start there?
Critical Hits - **** I've only recently started listening to this one, so I haven't explored the back catalog. But recent episodes include Mike Shea interviewing another blogger or industry person about a specific topic. I enjoy Mike a lot, and he does a great job conducting interviews. He asks good questions, and is always focused on pulling practical tips that can be directly integrated into folks' tabletop games.
Beer and Battle - **** Another live DnD action podcast. This one's overlooked, I think. It's focused on fun, but DM Peter tells a very good story (though sometimes can be a bit too heavy-handed with combat descriptions). The PC's know how to run their characters, and are genuinely funny people. I'm sort of taking a break from it for now, but that's more due to competition with other podcasts for space on my playlist than a lack of interest in continuing to listen. This sounds like the kind of gaming group that everyone wants to be a part of.
Critical Hit by Major Spoilers - *** This is the first live DnD action podcast I started listening to. It's ok. Rodrigo has created an extremely interesting world, and the story is absolutely top-drawer. I also quite enjoy DnD Brian (Randus), as he seems like a great guy and is does a great job as a player. Some of the other players, however, can be maddening. For some reason, I keep coming back, though I think it's mostly for Rodrigo.
The Tome Show/Dice Monkey/4geeks4e - *** I'm throwing all of these into one, which is probably not fair ...although they are all (as far as I know) basically part of the same family of podcasts. They are part of the same network (along with Icosohedrophilia) and often feature the same cast of characters. With the exception of the occasional (and quite good) Dice Monkey podcasts, the Tome Show and 4geeks4e podcasts tend to be pretty long and freeform. That's often not a good thing. Their product review episodes are worth listening to, but I often find myself skipping past substantial portions of their other episodes.