Most of what I could possibly say has been said by Tony. No point of double posting.
I come at this perhaps from a slightly different perspective.
- Because my dad was a hardcore jazz music lover, jazz drummer and became somewhat of a historian, I grew up on jazz roots from what began as Louis Armstrong Hot 5’s/7’s and went all the way through big band, swing, Dizzy, Bird, Clifford Brown and The Jazz Messengers. Hell, I heard music that came before Hot 5's/7's to see how that developed.
- When I saw “I grew up on it”… I mean I didn’t have a clue ANY other style of music existed until Soul Train began playing on our TV sets when I was about 12. Jazz (in its various forms) was all I heard… period.. and I heard it daily.
- When I hear about “going back” as in learning the history, if you listen to enough of any style of music you like, you will probably get curious enough to begin searching for the roots. Kids born today who may begin to love rock will probably eventually make their way back to Ringo and then what came before Ringo to get Ringo.
- Jazz is a style that is different from most other music forms, but it is still music. No need to over-complicate it. If you listen to things that spark your interest, be open to the search and you will find your answers to the evolution. You may find things you hate about it. I do… I don’t take to Avant-Garde very well. But many love it. So be it.
- As with any and all styles, be open to exploring and then figuring out what you want to take and what you want to leave.
Most importantly enjoy it… or not…. Your call..
ETA... For the last 3-4 years I've been focused on studying classical clarinet and that has presented some of the same concepts as the OP raises. Going back to listening... how far back and where... I approach it as I've stated above.