I'm going to give you a somewhat leftfield recommendation here, because I'm not going to recommend you an album or a song, but a film and a book:

The film is "Jazz on a Summer's Day" which is a wonderfully expressionistic concert film of the 1958 newport jazz festival, which has lots of classic jazz musicians playing and even besides it being a fantastic film, it also really helps seeing the performers in action if you want to understand the music.

The book is "How to listen to Jazz" by Ted Gioa (which you can find on libgen but I can't seem to connect right now). The thing about Jazz is that it's a genuinely different type of music compared to all Rock/Pop that developed as a mostly independent tradition. As such if you want to get into it your previous listening experience isn't going to help you much and might actually get into your way.