I’ll second this - cautiously. Even Kind of Blue can leave you cold if you’re new to Jazz. But one thing that might help - Miles Davis once said that he considers the spaces between the notes as important as the notes themselves. Listen to that album with that in mind.
Consider that music is about listener expectations, which are informed by their understanding of how musical phrases fit together. We have learned that when certain notes are played, other specific notes should follow. Chords have certain progressions in different types of music. We learn to listen for those subconscously. Tension builds as we hear the phrase being played, and then when it’s resolved according to our expectation it satisfies us.
Simplistic songwriters simply follow that pattern. Anyone can learn to play a straight 12-bar blues shuffle. But if that’s all you’re doing, it may not be very interesting. Better songwriters know how to ramp up that tension, do things that are unexpected, and then resolve it in unique ways - or leave it unresolved in order to leave the listener with an emotion or simply to be memorable.
There is a wonderful book on this subject that I highly recommend - it’s called This is Your Brain on Music. The author is a record producer and also a Ph.D in Neuropsychology who runs a music lab at McGill. He really digs into the nature of music and why we like it, and he grounds the whole discussion in real samples of music.
The book has a companion web site, Your Brain on Music, which contains audio samples for every example in the book. So he tells you what the musician is doing, and why, and then you can go to the web site and actually hear the passage so you can understand what he’s saying. A wonderful use of the web to supplement learning.
For example, this is what he said about Miles Davis:
Here’s a direct link to the page with the Miles Davis sample on it. It’s item #17. Give it a listen, and see if you can hear what he’s talking about.
Even if you don’t have the book, you can spend hours listening to the samples on those pages and reading his comments about them, and it will be a short course in music appreciation. But read the book along with it if you can.