I think recommendation systems actually are pretty good at recommending stuff you already like. I think a lot of us tend to buzz right past those as "well, obviously I've seen that already" and don't take note that it actually hit the nail right on the head for the first 5-10 results.

The trick is to find stuff that cuts across the space in some sense—stuff that's out of your current wheelhouse, but still has features that you would like. (E.g. I like the music of both David Rawlings and Mark Ribot, even though they are in wildly different genres, because they both have a certain ear for melody and relationship with dissonance that I like.) I don't think anyone is doing that well yet.