Recommendations for a jazz record which demonstrates vinyl superiority over digital

You should give an original Columbia 6-eye a try. It was not made with 65 year old tapes, but the first side will be slightly sharp. Worth a listen. It may ring your bell, or not.

Because Columbia was a big label, a lot of their records are out there making them cheaper to acquire a first run pressing.  Whatever the reason, perhaps degradation of the master tape, some of the great Columbia first issues are better sounding than digital reissues.  Ellington’s “Blues in Orbit” and Brubeck’sTake Five” comes to mind.  I like my records more than the digital reissues I’ve heard.  This DOES NOT demonstrate any inherent superiority of one medium over another, this is just some incidents where analogue examples sound better.  

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.