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No idea if this is the best place to ask but may as well try
Best place to start and/or best records to listen to?
In a silent way, which is superb
Not his best but easiest intro - then get into Bitches Brew.. thats a great record..
Get some live stuff as well.. then some coltrane..
Sketches of Spain was the first record I got hold of of. It's not his best though. I'd go with Kind of Blue for the best 'in'
It depends what you want really. If you're looking for something smooth and 'jazzy', Kind of Blue or Silent Way are both good. If you want weirdness and funk fusion, I'd recommend Bitches Brew (one of my favourites ever, with the best album art ever too) or On The Corner.
As a next step, I'd recommend Wayne Shorter's Ju-Ju though, as Shorter plays on a hell of a lot of Miles' best stuff, and his band features McCoy Tyner of Love Supreme (Coltrane, not Williams) fame.
are sketches of spain and on the corner, they're very different. on the corner is damn next.
Early '90s technically but I love that album. Sounds like early Ninja Tune. The rapping is really dated but in a good way. Definitely worth checking out.
it's got a big funk influence which makes it more digestable than a lot of jazz, to my ears at least. I'm no expert but that could be a good place to start if you're not majorly into jazz either.
It's all great. Silent Way kick started the whole fusion thing and is a great album to chill out to. Bitches Brew is his masterpiece but sonically very dense and very long, start with In a Silent Way if you're not sure. On the Corner, Live Evil, the Live at the Filmore East and West albums and Get Up With It are worth a mention too.
Kind of Blue is beautiful if you just want jazz. Tribute to Jack Johnson is another favourite of mine if you are more into blues or Sketches of Spain if you like classical. No easy answers my friend.
so here are some random thoughts on the subject:
- while everyone seems to go nuts for Kind of Blue, it's actually not radically different from his other Columbia stuff with Coltrane. Milestones or Round About Midnight would work just as well.
- His late 60s quintet with Shorter produced some great stuff. A bit more restrained and oblique than with Coltrane, but still fascinating. Try e.g. Nefertiti
- Bitches Brew was actually my first encounter with his stuff and it never really clicked with me. Miles fusion stuff is generally at its best on the mid-70s live albums. "Dark Magus" is mind-blowing cosmic funk. May be a good place to start if you're coming from a non-jazz background - would appeal to fans of Funkadelic, Jimi, Can, etc.
- My personal favourite is "Live at the Fillmore East: It's about that time" (careful, there are at least 3 Miles albums with "Live at the Fillmore" in the title). Shorter's last gig with the band, supporting Neil Young. It's kind of got the beginnings of the funk stuff with the complexity of the Shorter era and the closest Miles ever got to playing free jazz. Amazing, ecstatic far-out-there music.