Not knowing this album is like never having heard Beethoven's 5th

Remember back in April of 1800 when
Beethoven premiered his first symphony?
I don't either, but I've heard it was CRAZY.
He started on a dominant chord.
And it wan't even the V of the key?!
I know this is funny to think about now but shaking conventions up is sometimes a sign of creative genius, and that's exactly what Miles Davis was doing when he departed from his sound and style at the time and produced an album centered around modal tonality, Kind of Blue.
This album is really palatable, even to people who aren't into jazz. It's one of the jazz albums I could listen to front to back anytime, and a good litmus for you if you aren't sure whether you want to play jazz or not.
Even if you never listen to or play jazz, this album has an important place in the history of western music, so you need to know it. You will be filling one of the holes left by a strictly classical education.
Go ahead and listen to the whole album once just to listen, and refrain from analyzing. Come back for more ideas once you've finished it, or if you know it already go ahead and read on!

Now that you've heard the album you might consider the following as you listen the next few times
1) What are the characteristics of tone and timbre you notice? Rhythms?
2) How does the soloist give structure to their improv? Do you hear repetition, motif, or even patterns built on 3 or 4 'words'?
3) Can you hear the difference when Adderly takes over the solo from Coltrane? How would you describe any difference in their style or approach?
4) What are the musical characteristics of the rhythm section (drums and bass especially, but also the piano when backing up or "comping" chords)?
5) What else do you notice? Like? Don't like? What's new to you?
Enjoy this seminal work - it's quite possibly one of the most influential albums of all time and certainly of the 20th century. Davis' sextet changed history even though they didn't open with a dominant chord.

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