I'm going to make a recommendation here that I think is the best way for experiencing new jazz, so take it for what its worth but I'd say use Pandora or LastFM and just let it run.
Jazz is like any other art form, just experience a whole bunch without making a concious effort to do so.
I think its healthier for your understanding but thats just what i think. Too many people want to decide "I'm going to be intelligent, i'm going to listen to jazz" and then they come here bemoaning the death of "real music like jazz" and they end up getting screwed.
I don't think you're in the same boat but I'm trying to illustrate the issues with forcing it.
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