Rails Envy PodcastA very short weekly newscast. Gregg Pollack and Jason Seifer - of the infamous gag videos shown at the last couple Railsconf gatherings - read through a list of highlights from the preceding week in the Ruby and Rails community. Unfortunately there's rarely any in-depth discussion of the items, just a smattering of corny jokes which may not be everybody's cup of tea.
raleigh.rbRecordings from guest speakers at the Raleigh Ruby meet-up. Unfortunately months pass between episodes, and without the accompanying video/slides some of them are hard to follow, but many are timeless so don't be afraid to listen to the older ones.
Ruby on Rails PodcastGeoffrey Grosenbach - the most distinctive voice you'll ever hear - interviews the who's who in the Ruby and Rails inner circles, often ambushing them at conferences, which sometimes results in less-than-stellar audio quality. Episodes aren't regular in schedule, but frequent enough to avoid disappointment.
RubyologyThis podcast started out rough with more of a tutorial focus but thankfully host Chris Matthieu switched to an interview format and has since managed to catch some good movers and shakers in the Ruby and Rails field. Unfortunately there's no regularity to the schedule of episodes.
VideoObviously I can't watch video podcasts during my long commutes... well technically I could on my iPhone, but that wouldn't be wise while driving... so when I get to the office and find a few minute to myself these are the ones I watch.
RailscastsYou must live under a rock if you haven't heard of Railscasts. Ryan Bates continues to amaze me with his clockwork release of high-quality tutorials on Ruby on Rails tools and techniques. His podcast has been the number one contributor to my personal knowledge advancement in the field. If I were running a Rails development team right now these would be required viewing.
Ruby BanterDevelopers from the company Fingertips pair up to demonstrate clever Ruby programming concepts in a live coding session; they type in the code and run it while explaining it, often evolving the program over time to ease the viewer into a complex concept. Unfortunately there hasn't been a new episode in six months, but there's nothing stale about the back log.
PeripheralSome podcasts out there aren't declaratively focused on Ruby and Rails but most of their content is undoubtedly so.
The Web 2.0 ShowYet another podcast that tries so hard and fails so well to keep a regular schedule of releases. Josh Owens and Adam Stacoviak (and formerly Chris Saylor) corner the founders of successful and/or popular Web 2.0 start-ups and try to pry their secrets from them.
Pivotal Labs Tech TalksThe almost-self-explanatory name gives it away, they just need to throw the word "Guest" in there and it's all summed up. Pivotal records (video) presentations by guest speakers to their staff and selflessly publishes them for the betterment of the rest of us. Insert broken-record complaint here about the regularity of releases.