Back to Work (http://5by5.tv/b2w) is one of my favorites too. It's not tech-centric, but offers some fantastic insight into life outside of the text editor. And if you're lucky, Merlin might do a Dr. Phil impression.
I think it's actually hypercritical, but I like your name better :)
5by5's shows are great live as well. They keep a backchannel open on IRC at #5by5 that has a fairly regular crew. Dan's an excellent host in that he's adept at skimming the backchannel for direction and relevant items.
I realise that Gruber gets a load of bashing on HN of late. But I love The Talk Show. It hits just the right not of apple, tech, film and schoolboy sniggering.
I especially like the schoolboy sniggering.
I like his site, but he has a lethargic demeanour on podcasts.
The Pipeline is another good 5by5.tv show. It's just interviews made by Dan Benjamin, different people each episode, but it's usually great!
Looks like they have a bunch of great shows I look forward to exploring.