I have found that people often shy away from jazz, feeling that they "don't get it" or they "don't know where to start" or they are intimidated by what they perceive to be a very tight-knit group of insiders with secret handshakes and special codes. It can be hard to jump into the pool -- Where do I start? What type of jazz do I want to hear? What is good and what is bad? What am I supposed to be hearing?
Rather than being intimidating, in many ways jazz is really very accomodating and easy to enter, and from there easy to learn about and expand upon. Jazz is a very big tent full of wonderful sounds, and expands every day. When rock and roll came along, soul jazz and jazz fusion developed. Today, jazz is incorporating hip hop, sampling, and club music. Right now a couple of the biggest CDs out there are Esperanza Spaulding's "Radio Music Society" and Robert Glasper's "Black Radio" two discs with a distinct pop radio vibe by two jazz artists. And meanwhile, classic bop and swing go on as well, along side the avant garde, latin jazz, and other forms taken from across the globe. 
Being such an inclusive genre, the more one listens and reaches out, the more one can learn about jazz and what it is they like. And with that, one can come to the realization that jazz is all about the music, the feeling, and what it expresses to one's self that counts.
I have also found from my experience that once you are hooked you want to know more, know how jazz progressed from ragtime to dixieland to swing to bop to hard bop to cool jazz to fusion to avant garde and so on; how Lester and Coleman and the Bird influenced a whole generation (or two) of sax players; the importance of Louis and Clifford and Miles for trumpet players; and why "Kind of Blue", "Giant Steps", or "The Shape of Jazz to Come" were seminal recordings. To that end, I have found two highly readable and very different histories that I firmly recommend. While there are others, I found these two books to be eminently readable guides which beautifully explain the complexities and characters that are needed to grasp the underlying concepts and history of jazz. In my reading of books and book reviews, columns and blogs, it is clear that no single history is universally lauded -- criticisms abound about viewpoints, lack of depth on European influences or Asian and Middle Eastern influences, too much credit given to one artist or another, and biases towards one movement or another. But both books provide a lot of material and a great place to begin build a foundation.
Finally, the point is not that one has to read books and learn about jazz to appreciate it; rather that one can first simply appreciate it, listen to it, and enjoy it, and then if interested learn more about it from some great books. First and foremost, do not be afraid of jazz, grab a hold and take a great journey into a new and wonderous world.
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