Here's what I'm listening to this month. If you have any suggestions for things I might like, especially tech/programming podcasts, send them my way.
I listen to these regularly:
Major Nelson - Covers the world of the XBox360. News, reviews, interviews with insiders.
This Week in Tech - Leo Laporte and a cast of characters talk about the technology news of the day. Includes guests like Steve Wozniak. A bit chaotic but you get a good overview of the week's happenings so you can dig in more later.
Security Now - Very informative show about the world of computer security. Lately they have been doing information series covering networking, crypto, etc. Also covers practical tips.
The Dice Tower - Best of the board gaming podcasts. Reviews, news, and top ten lists. Gives a good overview of what is out there. Good place to become introduced to new games. The hosts are good natured and fun to listen to.
Engadget - This is last on my list but I usually get to it. Everything you need to know to stay atop the fast-paced world of cell phones and gaming systems.
These are not published regularly but I find interesting listening when I run out of regular podcasts:
Nerd TV - Interviews with lots of big names in technology. The interviews sometimes wander (Bill Joy's sailboat?) but are always interesting.
ITConversations - I've started listening to the programming series there. It doesn't appear to be getting any new podcasts but the archives are fun.