You have to WORK to appreciate Miles. Kind of Blue is his masterpiece, but that album, like most of his, is a snapshot in time. My personal favorite is On the Corner, because he didn't rest on Bitches Brew...he went even further into fusion on OtC. There's a little punk, a little hip hop (melody-wise), a lot of funk, and enough jazz to say this isn't pure R&B.
Here's a typical Miles play for me. I start off with Sketches of Spain, then Kind of Blue. Then Jack Johnson (I'm trying to give Bitches Brew a break for awhile). Finish with On the Corner and Tutu.
By the time I go from SoS to OtC, I'm still amazed at where Miles took jazz even after all these years.