Dan Carlin's Hardcore History is just awesome.
Dan Carlin's Common Sense suffers for the amount of effort that goes into Hardcore History. It takes him months to research and put out HH.
I keep up with EconTalk, ContraKrugman, Freakanomics and Security Now every week.
If you like Freakanomics give EconTalk a try.
I have a list of podcasts called 'On The Road' which is for when I have guests / gf in the car. This has:
Wait Wait Don't Tell Me
This American Life
The Dice Tower
Test and Code
Talk Python to Me