Recommendations for a jazz record which demonstrates vinyl superiority over digital

Richardbrand, With all due respect, you asked a very bad, very open-ended question with many ambiguous edges (the question pre-supposes that analog is in fact superior to digital and that there is or could ever be such a thing as a recording that could possibly prove such a tenuous proposition to all listeners), and yet some have tried to respond.  Amazing. No doubt this thread will live on for yet a few more weeks.

Kind of Blue is not and never was revered because it was a great recording per se.  It is revered because it was revolutionary in terms of musical structure in 1958 and probably because of Miles Davis' mystique and that of the other members of his group (Coltrane and Evans in particular). Technically, it was famously off-speed and originally in mono.

Traditional jazz hard to hear or understand when first listening to for most people. I do purchased Kind of Blue as my first traditional jazz album. It took me quite sometime to hear it properly. One day it clicked into place and it blew me away. 

I would suggest you purchase Sypro Gyra “Morning Dance”. It was my first non traditional jazz album back in the 80s and I still have and listen to it. 
 

Recommendations for a jazz record which demonstrates vinyl superiority over digital

Not possible because you'd need apples to apples to compare:

1. an analog system equivalent to a digital system
2. an analog (vinyl) recording equivalent to the digital recording
3. Cartridges sound different
4. DACs sound different

I'll spare you the hardware mumbo jumbo that you're not looking for. 

Here is an excellent recording that's very live sounding and has lots of dynamic range. 

Thelma Houston & Pressure Cooker: "I've got the music in me" Direct to disk LP

A sample cut

+1 @ghdprentice Eloquent and accurate as always.  I would only add that I find some very early digital masters suffer compared to vinyl.  To generalize, I find these are often albums where the original analog master was not well engineered and the problems exacerbated by early digital mastering techniques.  As you do, I find streaming recent  “digital remasters”  equivalent, if not better IMHO than vinyl.  Both vinyl and digital show differences in SQ between remasters, reflecting the recording engineers intent during remastering.  Streaming gives you the ability to explore all of the remasters published on the service and choose the one you most prefer with no monetary investment other than the service charge as your point out.  Most times these differences are subtle, but sometimes not.  Sometimes I even find the original low-resolution digital remaster better than the HD remaster.   It depends upon the recording engineer’s intent and your personal preference.