Vaniver comments on Things you are supposed to like - Less Wrong
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Try Pandora? Their licenses prevent them from playing songs too frequently, but they replay songs you upvote more than songs you don't (and never play songs you downvote), as well as learning from your preferences to give you new music you might enjoy.
I have found that their selection can be somewhat limited in some subgenres, to the point where you can have upvoted or downvoted enough that it no longer has new music it thinks you'll be interested in. (So far, I've only done this with Celtic Punk, and that was made easier by my dislike of The Pogues.)
I like Pandora enough that I pay for it. That said, there are some issues with it: