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Sorry if I made light of your question, but honestly, no one other than an entertainment lawyer should offer legal advice with anything related to copyright. This is an issue that we've struggled with and debated for years here on the GPPN but it hasn't prevented any of us from playing whatever the hell we want on our podcasts. And it's also why we spend a lot of time and effort encouraging bands and labels to upload their music to the Podsafe Music Network at MusicAlley.com. The bottom line is you're on your own. You run the risk of getting busted or "caught" for redistributing music that you don't have the "right" to redistribute. It's a pretty small risk, obviously, since we're all in the same boat and, as far as I know, no one has ever been busted for copyright violation for playing a song on a podcast. That said, I *have* heard that PROs (Performance Rights Organizations like ASCAP, BMI, SESAC, etc.) will go after podcasters as well as Web radio stations for artist royalties if they find out your show has played a song from one of their artists. It's all a big gamble... just like uploading copyrighted videos to YouTube. You may or may not get busted... it's anyone's guess. Good luck.
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"Go read a book and flunk a test." -Iggy