One of the best podcasts is a show you likely already know and love. The Ongoing History of New Music, hosted by Alan Cross (hear his episode of Toronto Mike'd here), has been heard on CFNY (and other Corus radio stations) for almost 25 years. Ok, it went on hiatus for a while when they let Cross go in 2011, but it returned in 2014 and is still in production.
The Ongoing History of New Music has also been available as a podcast these past few months. I've been listening to it and it's the exact same show you hear on the radio with one exception.