1. Miles Ahead
I bookmarked this article about Reid Miles, the chief graphic designer for Blue Note Records in the 50s and 60s ages ago. The work this guy did was super influential, defining the blue note style for years to come and spreading out to influence graphic designers of all types.
In my opinion, the archetypical Blue Not album cover featured a black and white photograph overlayed with a solid color. A vertical bar of the same color ran across the image with bold text over it. My next favorite type of cover reversed that formula by expanding the text, making it the main focus of the design with a smaller band of photographic images. There are online archives which allow us to examine decades worth of Blue Note covers. These two design concepts recurr continuously, but never manage to seem cliche or boring.
When it comes to the music on these records, though I obviously haven't heard them all and am not really a Jazz expert, my favorite is from the Miles Davis and Milt Jackson Quintet/Sextet. I bought this record at a church sale years ago and listened to it nonstop for months. Eventually I bought it on CD and sold the LP on ebay for peanuts.