I listen to podcasts more than I listen to music, haha. Here's my choices:
Buzz Out Loud: I've been listening to this one since episode 316, so that's 760 episodes as of now. :) Great show, it's a great way to keep up with news in tech, and it's just long enough for my commute.
The 404 (CNET): I've actually just started listening to this one, and it's actually very funny. Give it a few episodes to kinda 'get to know' the hosts, and you'll most likely enjoy it. It's mostly random, but they cover some actual news sometimes.
Gadgettes: Another CNET podcast, it's a once per week podcast, and it's pretty freaking funny most of the time! :)
Buzz Report HD: One of my few video podcasts, I usually stick to audio, as most of my listening is done while driving, but this is a short, humorous take on the week's tech news hosted by Molly Wood.
Windows Weekly: These are usually about 1-1.5 hours long, but Paul Thurott and Leo Laporte really work well together, and it's very informative and humorous at the same time.
This Week in Tech: Absolutely fantastic show, but they often reach or exceed the 2 hour mark, so I end up having to skip episodes to keep up, I just don't have enough time. :P
Onion News Network (Video): What more can I say? If you don't watch the Onion's videos, you owe it to yourself to start watching them now. I suggest starting with the one entitled "Should We Be Doing More To Reduce The Graphic Violence In Our Dreams?".
Scam School: Brian Brushwood is just funny to listen to, and you can learn some pretty neat tricks too. I've never had a chance to put any of them into practice, but hey, you never know when it could pay off to know how to jam a nail through your face.