I wrote about Mac OS Ken in my work blog, kicking off entries about tech-related podcasts. As far as non-tech podcasts go, Coverville is easily one of my favorites. Brian Ibbott releases episodes several times a week chock-full of cover song goodness. Other than becoming more refined over the years, the show has stayed true to its roots. I may not always enjoy all the music, but even my least favorite shows are interesting enough for me to listen through.
I've been a long-time fan of cover songs and actually didn't realize it. I grew up in the same city as The Carpenters (Downey, CA), who did a lot of covers; my favorite of theirs is "This Masquerade" (most people probably know the George Benson recording). Also, when I was young my mom had several Peter Nero records which contained mostly covers, and I enjoyed listening to those. The bands that would come to my high school and play during assemblies? Covers.
Many of the Coverville shows are grouped by theme, such as covers of a particular artist's songs, cover songs in a specific genre (a capella is the most popular), or songs relating to a particular holiday. Other times he'll play a collection of covers submitted by indie artists, and he has a weekly show for requests.
While the show focuses on cover songs, every now and then Brian throws in "Originalville" songs which are ones where the cover song is more well known than the original. For example, Mark James recorded "Suspicious Minds" before Elvis did. "I Go Blind" by Hootie and the Blowfish? Originally released by 54-40. And so on.
It's hard to say which shows in particular to recommend to a new listener, so if you'd like to try out Coverville, I'd recommend going backwards through the show notes until you find one that sounds interesting. If you like a particular artist or group, it's very possible he's played a cover either of or by that performer. Just don't be surprised if you start buying more music after listening to several shows.