Sam Enright assembled a friendly Beginner’s Guide to Miles Davis. If you’ve always been curious about jazz but never really managed to get into it, then this resource might serve as a good starting point. I cannot say I’m one hundred per cent aligned with his choices, but we’re close. One remarkable statement I concur with is this one:
Jazz is so interesting to me because of its fusion of intricate underlying structure with improvisation and spontaneity. As Ken Burns put it, jazz is “familiar, but brand new every night”. Moreover, I enjoy the intellectual demandingness of jazz as a genre. Jazz musicians seem to be the most thoughtful and intelligent of any genre. Many of the more Avant Garde songs mentioned in this post don’t sound good unless you’re really concentrating. Some of it sounds cacophonous to a newcomer. This is why jazz is considerably more difficult to get into than other genres and has a lack of listenership among the youth.
Sam put a lot of effort into his selection, and it shows. Should his list be overwhelming for you, my shortcut advice would be: listen to Kind of Blue, especially the first two tracks, So What and Freddie Freeloader. If they don’t move you, I am sorry, you’re probably not a jazz person.