I'm a jazz enthusiast, not an expert. But I do have 33 of Miles Davis' CD's, and about 300 overall jazz titles, so I have some familiarity. IMHO "Kind of Blue" may be overhyped, but not overrated. It's as great an album, today, as it was in 1959. But if it doesn't sound as "breakthrough" today as the hype might lead you to believe, it's because it pulled jazz in it's direction- it's important because it changed the genre.
Aside from the fact that it's just great music, one of the things that's unique about KOB is that jazz musicians of the day were just as taken with it as the average jazz music lover. They tried to emulate it and capture that special quality that we still hear today.
Whether Miles achieved his personal objectives is an interesting point (raised above) but irrelevant to the importance of the music. When the music became part of the public domain it also became bigger than him and concurrently became a lot of different things to a lot of different people, both in and out of the world of music. No different than the Beatles in the 60's, Elvis in the 50's or Sinatra in the 40's. Beatles music today sounds so familar and comfortable that you might ask "What was all the fuss about?" It's easy to forget that the reason it's sounds so mainstream is that it redefined all the popular music that followed. Only when viewed in the context of 1964 can it's impact be understood.
But like anything in life, we all see things differently. My fellow audiophile friend sold his copy of Kind of Blue- he just didn't get it at all. I on the other hand, still consider it my favorite jazz disc that gets better with each playing. Because the more I listen to other jazz CD's, many of which I consider to be excellent, the more I hear the influence of "Kind of Blue."
