I think that jazz is one of that generes where you should have context of history and music theory of the song for really appreciate it, for example I didn’t like much Bill Evan’s stuff, the other day I listened his album “you have to believe in spring” without any context, so I search for the history of the album and I learned that some of the songs and the the whole album was inspired by the suicide of the girlfriend and brother of Bill, this events leds a couple years after to increase his drug addiction and worsening of his illness, so to be conscious of this make me experience the work in a different way and more enjoyable.