And now there is "Birth of the Cool -- Miles Davis" on Netflix. I liked the new sound more than BeBop which came first.
For a different take, I've always been particularly fond of systems built on RNG (or similar) for content discovery.

Deezer has a pretty impressive collection of music, and a decent API. I did a random search over integer ranges for the Album ID field to find where most of their collection lived (I tried to keep below a 33% retry rate for invalid guesses). Then hobbled together this:

Every refresh gives you a different album from their collection. The server handles guessing (and re-guessing until one exists) album IDs and returning the Deezer metadata.

If you want to discover odd music that breaks you out of your comfort zone, I'm not sure there is a better way than praying to the RNG gods ;)