The Ruby Show – The Ruby podcast, with Dan Benjamin and Jason Seifer.

Ruby5 – Frequently-released short podcasts on what’s new in the Ruby and Rails community. By Gregg Pollack.

Ruby On Rails Screencasts – Free Ruby on Rails screencasts

SD Ruby Podcast – Ruby podcasts by the San Diego Ruby community.

Ruby Pulse – Free Ruby-related podcasts.

Ruby Kickstart – Hours of free screencast to teach you how to program in Ruby, with loads of free material, quizzes, and goodies.