Recommendations for a jazz record which demonstrates vinyl superiority over digital

Kind of Blue is not a well recorded album.  The music is, however, beyond reproach. Perhaps my favorite jazz album.  My recommendation is Boss Tenor by Gene Ammons.  As to vinyl vs digital; I have a very high end system with both. The key is the quality of the mastering on either format. I love both formats but recommend folks on restricted budgets will get better SQ from a well chosen digital system.   

I have many of the recordings discussed here. Before making an A/B comparison, you should be able to hear differences between: streaming and CDs, CD and hi res. If you cannot, probably your setup won’t do a good job of comparing digital to vinyl. 
 

If want to go ahead, I suggest using the Pawnshop recordings. I don’t much like the music, it is too showy. You can find cd and hr of some Pawnshop versions on Qobuz and Tidal. And you can get a vinyl version on Amazon. Also, Paul McGowan of PS Audio did a short video on Pawnshop. 
 

Personally, I prefer vinyl; but vinyl is like a boat - a hole in the water that you throw in.

Throw money in

"Kind of Blue" is a very well recorded album. It is especially open and airy, which makes it easier to sort out tonality and timbre of individual instruments. An easy comparison of what you hear on the record to the sounds of those instruments you've heard before make this album a great, uncomplicated reference.

"Kind of Blue" is surely not the last word on recording mastery, but it was recorded and mixed better than most. It is disingenuous to claim it is not well recorded.

I would agree that "Kind of Blue" is not well recorded.  The Kevin Gray remaster is an improvement, but it still falls short.  However, I would still be happy listening to Jonl  on a 1960's am radio.