Kind of Blue is teh epic for sure. Birth of Cool of course as well, yes, Bitches Brew was significant, but to be honest I usually remember him more for who he worked with/inlfuenced (Parker, Coltrane, Shorter, Hancock, Zawinul, etc.) than for his soloing/recording. For sure he had a major impact on the dominant jazz style of the day for nearly 20 years, and for his body of work as a band leader few, if any, compared.
A couple of weeks ago I heard the premiere of "Sketches of Brazil", a long-form composition by Miles' former 80's keyboardist (and nephew) Robert "Babee" Irving III. It took the idea behind "Sketches of Spain" into a Brazilian/samba direction, combining original melodies with re-arrangements of Brazilian compositions by Heitor Villa-Lobos. Gil Evans' son Miles Evans played in the trumpet section and Wallace Roney played a very Miles-ish lead trumpet. I hope this gets onto CD. (http://www.sketchesofbrazil.com/Sket...azil/Home.html)
Huge Miles fan here; prefer the bop but even like his funk period. A great trumpet player and real visionary. Get the Kind of Blue 50th anniversary set. Also look for the chronically underrated "Miles Smiles" album. I like Chet too but he can't hold Miles jock strap.