Recommendations for a jazz record which demonstrates vinyl superiority over digital

I have a lot of jazz vinyl and IMO the best sounding recordings are all in the studio. But the best performances are all live, which tend to generally not be great recordings. My personal favs are piano, guitar and big band. Not a huge fan on New Orleans style.

So its a bit of a two-edged sword. Having said that, my list is below:

- Boss Brass - Direct to Disc on Umbrella label - wow for the music and sound - big band jazz

- Harry James - D2D on the Sheffield Lab label - big band  - I think he did 2,3 albums

- Miles - Prestige Box set - from the late 1950s and early 1960's - before KoB - 45rpm by Analogue Productions - wow

- Bill Evans - Riverside Box set - AP again - AP IMHO does the best remastering and pressing of jazz recordings - Evans also has some live recordings that are great performances - sound is pretty good on them.

- Jazz at the Pawnshop - the original pressing or a new one on 2XHDNS vinyl

- Joe Sample - Ashes to Ashes and Spellbound; he had the best of the best players and engineers on these two and it shows in the sound.

- Oscar Peterson - Strictly for my friends - box set

- Grant Green - AP re-press and re-master - guitar

- Sonny Clark - AP re-press and re-master - piano

- Lyn Stanley - female vocal - new arrangements of standards from the 1950's that Sinatra did; She has the best of the best studio musicians and engineers. Great sound and performances if you like her style.

- Getz-Gilberto - Girl from Ipanema - 45rpm by AP. Another version just came out - I think on Impex label, but not sure. One of my GOAT albums for sure.

Hope this helps out. And enjoy the journey. I sure am.

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