You may have already read how I first heard Miles' music, so I won't repeat it. I will try to explain why I love his music so much.
Aside from being one of the most prolific creators in jazz, Miles has brought to jazz several crucial evolutions - introducing "Cool" jazz and eventually sort of inventing Fusion Jazz.
But I think it is the Cool style that Miles introduced that made him such a favourite of mine. The mellow, smoky, evocative style is my favourite type of jazz music. The brooding contemplation that allows so much emotion to flow through the music. (It also goes well with the dark stuffy atmosphere of jazz clubs).
What is interesting is how Miles frequently interpreted his Big Band pieces into the new Cool style, and then sometimes reinvented those same pieces as Fusion creations. Just another attestment to his tremendous creativity and improvisation skills.
So if you are ever looking for a jazz album and do not already own Kind of Blue - try it, I doubt you'll be disappointed. Other excellent albums are - Sketches of Spain, Birth of the Cool and Miles and Coltrane.
I must add this though - Miles has produced such an immense body of recordings it is hard to point to just a few albums and say - these are the best.