CATO’s daily podcast has been quite informative, as is FMNN eradio.
I heard about Dan Carlin on Free Talk Live. I’ve enjoyed his rants on occasion; his tendency to deliver his points with emphasis, in a fashion reminiscent of Captain Kirk, can be distracting (or amusing) at times. I recommend his programs anyway. They do get the grey matter flowing.
As far as regular radio format, Jeff Ward in the afternoons on KLBJ-AM is probably the best three hours of local talk to be had on a daily basis. It’s too bad the morning show is so lackluster.
Most people will direct you to iTunes if you are looking for audio content to transfer to a handheld device for playback. I have no use for iTunes, I don’t have an iPod (it’s those pesky DRM issues that go along with iTunes purchases) although the iPod craze is to be thanked for providing a new market for the talk format. However, you don’t need iTunes (or an iPod) to download and listen to Podcasts. If you’re just looking for some new content to listen to, check out Podcast Alley. Get an RSS aggregator for your browser (I use Firefox and Sage myself) and start searching. I was able to find and download podcasts for Penn Jillette and the Mises Institute (recommended by a fellow FTL listener) within minutes using these tools. Loaded up and ready to go on the old Treo 650.
Keeping a constant stream of information going is critical for a news-talk junkie like myself.