By far, my favorite podcast is This American Life. If I were stranded on a desert island and could only receive one piece of media regularly, it would be TAL. If by chance you aren’t familiar with this show, it’s a weekly radio show by Chicago Public Radio. It’s kind of a documentary magazine format with different stories all revolving around a theme. The stories tend to be personal stories, sometimes told by the participants, sometimes a reporter will edit together different materials, mostly interviews. At times the stories are funny, at other times the stories can be deeply moving. They are almost always interesting.
Every week, the latest episode is available for download free of charge. Also, if you are online, you can listen to their entire back catalog of shows, going back years. Older shows can also be downloaded for 99 cents from itunes.
One of my favorite episodes of recent memory is episode 355, The Giant Pool of Money which was a great dissection of the sub prime mortgage mess, told through individual stories from every link in the chain from home buyers all the way up to Alan Greenspan. This show, made in conjunction with NPR News, spawned another one of my favorite podcasts called Planet Money.