TWIT A network of about a dozen technology related podcasts started by Leo Laporte after TechTV was bought and dismantled by G4. Many of the former personalities from TechTV can be found here.
This is Screaming halibut One of my favorite comedy poscasts. No longer having new ones made, but there is a large archive. They used an e-mail of mine as the springboard for a sketch about how to spell a maniacal laugh. (The episode on 7-10-2006, titled "He aint heavy, he's my halibut") You need to start at the beginning as they have a cast of recurring characters that they introduce over time.
The Monkey Box another funny, though sometimes rude comedy show. The recent ones are leaning more toward video than audio.
The Working Podcast This started out with a theme of "work sucks", and has evolved into a good work advice podcast, but with a snarky attitude. The attitude now is more like "Work sucks, but being unemployed sucks more". He tries to do a weekly show, but in reality it is only one every couple of months. Large archive of prior episodes.
Think I listen to a few podcasts? They saved my sanity when I had commutes of 2 hours or better for a couple of years.
I have a serious crush on this man, but that aside his podcasts are awesome - and have appeal right across the board in demographics - my kids to my own parents have been converted into fans of Jeff's music. :)
They do a weekly show on tech/web culture. It's pretty entertaining when they get on random rants. Especially when they don't even pertain to the stories they supposed talk about.