My podcast line up is as follows:
CagCast - Cheapassgamer's podcast. Wombat is either annoying or insanely funny. Shipwreck is the brains, and Cheapy keeps things moving.
Critical Hit - A Dungeon's and Dragon's podcast. I do not play DND, and I know nothing about it, but these guys generally fall apart midgame anyway.
Dan Carlin's Hardcore History - He charges for old episodes (his series on Hannibal was amazing), but the new stuff is free. The way he talks about history is almost like he's reading you a great book.
Giant Bombcast - It's the Bombcast.
Highlands: A Peephole History - Kevin Smith's podcast about Highlands.
Hollywood Babble-On - Kevin Smith's celebrity news/film podcast with Ralph Garman (my personal favorite of the Smodcast podcasts)
How Did This Get Made? - A Podcast that discusses terrible movies that are currently in theaters.
Jay and Silent Bob Get Old - Still a good podcast, but since they're playing at the John Lovitz Comedy Club now, they seem to do more visual gags that don't play on the podcast. (IE: Let Us Fuck!)
Joystiq Podcast - I get tired of Chris Grant going on and on about his Iphone, but Justin's funny in a snotty know-it-all style, and Ludwig is pretty interesting himself.
Live From Smodcastle - Occasional shows recorded at Kevin Smith's podcast studio, the most interesting (imo) being Having Sex With Katie Morgan.
Midwest Wasteland - The guys from VGN would get together and discuss their childhoods and current lives, topics like being broke and crazy ex-girlfriends.
My Brother, My Brother, and Me - This one's hit or miss for me. I don't always listen to the entire episode, but sometimes they're real gems.
Plus One - Kevin Smith's podcast with his wife. It's not quite as funny as some of his other podcasts, but it's interesting all the same.
Smodcast - Kevin Smith's first and main podcast with Scott Mosier. Probably second only to Hollywood Babble-On in terms of off the wall humor. I still chuckle whenever I think about "Forgeticus"
StarCast - I don't like, play, or know much about Starcraft, but this podcast is interesting. Listeners send in tips and strats, and the hosts discuss the Pro-gaming side of Starcraft in depth.
Tell 'Em Steve-Dave! - The podcast of Kevin Smith's childhood friends Bryan Johnson and Walt Flanagan. These two can be extremely oversensitive and whiny sometimes, but they can also be extremely funny.
This Is Only a Test - Tested.com's podcast
Video Game News Radio - Group of Midwestern guys that listen to hair metal, drive trucks, pay child support, and play video games. Kevin and Brian bicker a lot, and it is very amusing.
Video Game Outsiders - John and Michelle, usually informing us that Kyle couldn't make it this week, host the show. I don't think Michelle really games outside of WoW, but John is passionate about it, and probably clinically insane.
Weekend Confirmed - Garnett Lee's post Listen UP podcast. Brian Leahy just quit Shacknews, so there's no real "hardcore" gamer perspective on the show currently, and Garnett is often preachy and pretentious. That said, show is good.
Those are my weekly podcasts, most of which I feel have a comedic bent. They don't all update every week (Midwest Wasteland, Dan Carlin, Highlands, etc.), but I listen to podcasts for a good five hours a day, and I only run out of new shows during the holidays and such.
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