By now most of my Macintosh friends and the even the few friends who still use Windows (yes... I still consider them friends) should have tried the new iTunes 4.9 with Podcast compatibility by now.
I have been listening to all kinds of Podcasts for the past 8 months. The podcast "Fly With Me" produced by Joe d'Eon, a First Officer from an US Airline - well as of July 4th he has been promoted to Captain - is very funny.
Below is a quote from his web site to give you some idea
Hear from flight attendants and pilots as they tell you what goes on behind the galley curtain (and behind the cockpit door). The author is an airline pilot who takes his recorder on trips with him -- funny stories, insider info, and interesting insights.
There are content like this on various airline specific discussion forums, but because this one is in audio format therefore it is much funnier.
Even if you are not in the Airline industry you will find this an entertaining Podcast to listen to, and for those friends who are in the airline industry, they will definitely be able to relate.