Here's the tip: Find somebody who is knowledgeable about jazz music and who shares similar tastes as you and ask them what they are listening to. Buy their recommendations for starters as you continue to build confidence in your own knowledge and familiarity with your own tastes. If you can't find such a person or don't trust their musical sensibilities to be close to yours, I suggest picking up a book like the The Penguin Guide to Jazz Recordings and working on their recommended albums, of in the Penguin case, the "Core Collection". (That's mostly what I am doing now.) Also, either of Levine's jazz books, "The Jazz Piano Book" or "The Jazz Theory Book" have extensive discographies in the back. Reading through those should give you some idea of where to look and what to buy.
Here's the logic behind the tip: Did you know that two of the four CD's in the Clifford Brown complete set are the same as Art Blakey at Birdland Volumes 1 & 2? If you did, good for you. If you didn't, you should read up before you make your purchase. I didn't and ended up getting Art Blakey Vol. 1 and the Clifford Brown set in the same weekend. Fortunately, I realized my mistake at volume 1 and did not repeat it with volume 2, but had I just done a little research beforehand, I could have saved myself the ignominy of buying two of the same recordings under different guises. Another example: If you heard the name "Sun Ra" and that he claimed to be from Saturn and that his band was called "Arkestra", would you expect straight up, original, basically timeless big band type swing music, or something else, maybe something more esoteric involving African drums, gongs, ethnic chanting and such? Well, if you knew it was both, again, good for you. But if you had no idea that something that has all that "esoteric" stuff by a guy from Saturn named Sun Ra could sound so much like classic swing, well, don't you think you should have studied up?
My basic point is, there is no bad way to discover new music, artists, and styles. Music is all about experimentation, and jazz is the embodiment of musical experimentation. But when spending money on music, I prefer some guidance.
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