I've been listening to podcasts for a while and I want you to listen to them too. Here's a list of my favorites.
Back to Work
Merlin Mann and Dan Benjamin talk about how to be better at life, especially in regards to your job and any other kind of work you do.
Favorite episode: Brick Building Full of Lies
Roderick on the Line
Again, I'm a huge Merlin Mann fan, so it's hard to not recommend this one as well. He and John Roderick just want to help you. Why won't you let them help you?
Favorite episode: Everybody Knew What Mr. Finnell Did
Judge John Hodgman
Deranged millionaire John Hodgman renders judgement on any dispute set before him. He's a genius of wit and I can't recommend this one enough.
Favorite episode: Out of REC-order
You Look Nice Today
This is the canonical Great Podcast That Some Might Not Understand. Basically, it's absurd, well-edited humor. And it comes in at the middle. So, buckle up.
Favorite episode: Razzledazzle
The YoGPoD
This one isn't quite for everyone. It helps if you're already a fan of the Yogscast guys. Simon and Lewis are such a terrific duo and it's quite entertaining to just listen to them discuss anything. Also, don't miss Simon's voices. They're solid gold. It updates sporadically, so don't expect weekly episodes.
Favorite episode: Dungeons & Dragons Part I (sorry, no permalink)