Miles Davis: On The Corner (1972)
So given my lack of expertise on jazz, I'm not even going to pretend to offer any sort of critical assessment of this album, as I'd almost certainly sound like an idiot. I just know that I have a soft spot for the Miles Davis albums from his late 60s/early 70s electric/funk/fusion period. And while the landmark Bitches Brew is the name most people drop (for good reason), I'm a little more partial to On The Corner.
I picked this up not because I had any plans to start exploring jazz; rather, the album appealed to my love of both extended exploratory Dead jams and early 70s funk. The original On The Corner was just a few jams, crazy bass and funky guitar and propulsive percussion (like I said, I'm not a jazz guy, so pardon my ridiculous adjectives). At times you almost forget Miles is there, and when his trumpet does dominate the sound, it feels more like free-form psychedelia than traditional jazz.
Even better than the original album is the sprawling Complete On The Corner Sessions box set from a few years ago, which has a few hours of the unedited jams that were whittled down for the official release, more than enough grooves to get you through a long afternoon. So, again, I don't have the tools to evaluate whether this is a fair or good or great representation of Davis' work, I just know I find it a really cool listen.
Here's a live set from '73 which is pretty amazing: