I'm a big Miles fan. Of all the great jazz musicians, his music is probably the most difficult to shoehorn onto a single CD because his style changed from decade to decade and sometimes from year to year. As MD pointed out, there are too many good songs, but with jazz, especially bebop and postbop, it never sounds the same to any one person, so really, the best Miles compilation is subjective.

I'd much prefer listening to an entire Miles Davis LP instead of a compilation. It's much like listening to Led Zeppelin II, that's an album meant to be heard in its entirety. Heartbreaker, Living Loving Maid, Ramble On, Moby Dick, and Bring It On Home have to listened to together and in that order with no omissions.

It's the same with many of Mile's albums. Go instead with burning his best albums with complete song lists to capture his many sounds.

These four Miles Davis albums were landmarks, revolutionary in how they changed the jazz landscape:
Birth of the Cool
Miles Ahead
Kind of Blue
Bitches Brew

I'd add the following as "merely" evolutionary:
Nefertiti
Porgy and Bess
Sketches of Spain

As much as I enjoy his musics, there's a few more bop era musicians that I like more - John Coltrane, Thelonius Monk, Charlie Parker, Wes Montgomery, and Art Pepper. I'm not a big fan of the trumpet.