Everyone should listen to This American Life.
It's produced by Chicago's NPR station weekly, and is all archived free online. And it's so good. They range from ok up to really profoundly excellent.
here are the 'staff favorite' which is kinda like a best-of
http://www.thislife.org/pages/favorites.html my personal favorites that are on this page are:
Act V: a version of Hamlet performed by prison inmates: murderers doing a play about murder.
My Pen Pal: a woman who as a little girl ended up pen pals with Noriega. Hilarity ensues.
Babysitting: Really funny stories about disastous babysitting experiences.
Ok just trust me. Listen.