From the Miles Files: Getting started

Call this a common theme. Gushing about Miles Davis. This is what we do.

By Pico:

1) Miles Smiles 1966 - The best album by Miles' best band. The playing on it is out of this world and the compositions, half of which are by the saxman Wayne Shorter, are sublime.

2) In A Silent Way 1969 - The first full fledged fusion record, and his best. In many ways, it's Kind Of Blue set to contemporary instruments and rhythms. If you can, go for the 3-CD Complete Silent Way Sessions.

3) Milestones 1958 - Kind Of Blue belongs here instead, but since you have it already, this would make a fine substitute. In actuality, it's a better introduction to Miles' pre-fusion work than Blue, because it incorporates all the jazz forms he championed up to that time: bop, cool, and modal. Plus, you still get Cannonball and Coltrane together. What a deal.