This American Life

Image by Getty Images via Daylife

This American Life is an excellent radio program out of Chicago, which tells (real and fictional) stories of people's lives. It has a free podcast, and also free access to its archives. I highly recommend Episode 355: The Giant Pool of Money and Episode 289: Go Ask Your Father, but really I have enjoyed almost every episode I have ever heard (and that is many, many episodes).

Image shows Ira Glass, the show's host.