If you're a Facebook user, you might want to check out my company's FlyFi Community Playlist app which lets a Facebook community collaborate on a playlist... but it's more than a playlist because it also provides tracks related to the manually entered ones.
A fair number of the tracks are legally downladable free MP3's, from superb artists like Randy Newman (one of my personal top 5 artists), Ani DiFranco, Suzanne Vega, Dar Williams, and many others.
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