Hi Jimellow. The best thing to do, after picking up a few initial recommendations, is to follow one person you like off of a recording. For example, after I got into "Kind of Blue" by Miles Davis, I started to follow the recording careers of John Coltrane and Bill Evans, who are both sidemen on that album. With that, here's some concrete album recommendations:
Louis Armstrong - it's hard to recommend an album of his because, well, there were no such thing as albums when he was doing his important stuff. I like the Naxos Historical Series (volume 1 is my favourite). Basically anything with the Hot Fives or Sevens band.
Miles Davis - Kind of Blue - I won't get into the "modal" thing with this album, but it's an extremely significant album for Miles. Another example of him forging ahead. Great band and you'll get interested in all members here.
- Miles Ahead - My favourite of Miles' collaborations with Gil Evans in an orchestral setting.
John Coltrane - A Love Supreme - A great example of the Coltrane quartet. This is representative of the long forms they were getting into at the time and a rare example of devotional jazz which I think helps one to "get" Coltrane.
Charlie Parker - it's hard to do one album. If I had to do one, Bird and Diz would be a good bet, especially since Dizzy's on there too, but if you can find the "Dial Master Takes" or the "Savoy Master Takes" in an affordable package, get those. I have the above collections in double disc sets from a label called Definitive records.
Bill Evans - I'm getting more and more tired of his later stuff, but you just can't beat Sunday at the Village Vanguard for putting you in a certain mood. This is just piano, bass and drums and it'll get you in a place those other recordings can't reach.
That should be enough to start with. I've avoided vocalists because I expect you'll get enough of those recommendations.
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