Jazz for aficionados

o10, Ry has such a variety in his recordings I think it is impossible to make an absolute recommendation -- it may all depend on what sort of listening mood you're in at the time.  I will say I've only heard one of his which I didn't enjoy, "Bop Till You Drop".

For all that, possibly his most popular recording and thus a safe place to begin is the "Buena Vista Social Club".  He doesn't play lead, instead allowing a great group of little known (within the US) musicians enjoy the spot light.  I believe he was the producer though so deserves much credit for pulling off the the whole thing.  So yes, it features underdogs!

https://www.youtube.com/watch?v=JNYOVEXJBBM

Great and very eclectic musician deserving of all the accolades.  Ry Cooder was indeed the producer of the Buena Vista Social Club project and deserves a great deal of credit, as pryso says, for making it all happen.  Interesting project on several counts.  First, it all happened practically by accident as the original project was supposed to be the recording of a musical collaboration between musicians from Mali and modern Cuban musicians.  The African musicians never made it due to some diplomatic red tape and so Cooder decided to record traditional Cuban music instead and embarked on finding musicians who were active pre-revolution and were mostly retired.  Not only were these musicians not known in the USA, many of them were not known to younger generation Cubans.  Beautiful traditional music from pre-war Cuba.  I love the record, but have one pet peeve.  As much as I like Ry Cooder's guitar playing, he should not have played on the record.  His playing is mostly tasteful, but it really doesn't fit the style of the music.  The sound of slide guitar is something that is never heard in this music.  Paquito D'Rivera tells a funny story of the Cuban musicians looking at each other while recording and shrugging their shoulders as if to say "well, he's the one with the money" 😏.   Still, a record that was hugely influential in exposing people all over the world to this beautiful music. 

Re Coltrane "Live At The Village Vanguard":

That great record is actually only part of the music from a four day run at The Vanguard available in its four day entirety as "The Complete 1961 Village Vanguard Recordings".  O-10, that's the one to get.  Of note is the fact that it is the first recording featuring the classic Coltrane rhythm section of McCoy Tyner, Jimmy Garrison and Elvin Jones.  In my book, one of the two greatest rhythm sections in all of jazz, along with Miles' '60s rhythm section with Herbie Hancock, Ron Carter and Tony Williams.  Fantastic music.  Ghosthouse, here's a couple more mold-breaking, very adventurous jazz also happening around that time:

https://youtu.be/MOhKYOQK-dw

https://youtu.be/xbZIiom9rDA