Now that my musical tastes are pretty much stuck in my early-90s college era, I've found myself gravitating more toward podcasts for entertainment. One that I've found particularly interesting/entertaining is Back to Work. The hosts are Dan Benjamin, who is the Rupert Murdoch and common thread of the 5by5 Network and acts as the straight man to Merlin Mann, who made a name for himself in the productivity arena. I had been a casual follower of some of Merlin's earlier work, like 43 Folders and stumbled across this show by happy accident.
The basic format of the show is a collection of tangents with a theme/topic thrown in at some point. Dan and Merlin let their geek flags fly proudly, discussing Star Wars, Comic Books and Software Development Tools with equal ease. The side discussions are entertaining on their own, and the hosts bring their own insightful and often counter-intuitive views on various life topics like persistence, productivity, etc. They tend to be long shows (90 minutes is not uncommon), and riddled with inside jokes, but are definitely worth a listen.