Recommendations for a jazz record which demonstrates vinyl superiority over digital

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.

@herman How do I know if I have "vinyl hardware properly set up and optimized" without something worthwhile to play on it?

Yes, there are a lot of variables but I want to eliminate poor recordings (your variable 1,000,001) as a source.

Maybe my question should have been "What half-a-dozen beautifully produced jazz recordings currently available on new vinyl records should I buy"?  I don't think replay hardware has any bearing on the answer to this question?

Ultimately, I want to be able to judge whether it is worth spending any more on my vinyl hardware, or stick with digital.

As luck would have it, Hyperion has just released vinyl versions of Marc-Andre Hamelin playing Shostakovich's First and Second Piano Concertos.  The first includes trumpet solo, one of my wishes!  For years, the second movement of the second concerto, recorded in 2002 on SACD, has been the second track I always use for evaluating speakers.

I have ordered the two-record set but have no idea what the weight of the vinyl is, nor its colour, nor even its speed.  At 10 minutes average per side, it might be 45-rpm.  Ironically, the third work on the SACD is Shchedrin's Second Piano Concerto which features a jazz trio (piano, drum kit and vibrophone) but it is not on the vinyl.

Shostakovich had a difficult musical life and loved jazz, not a strong point in the Soviet Union, A few days after Stalin walked out of a performance of his opera, Pravda described the work as a 'cacophonous and pornographic insult to the Soviet people'.  Stalin had a deserved reputation for eliminating people, and was Pravda's main arbiter of taste as its music critic.  Most of Shostakovich is tortured, but the tranquil test piece I use was written after he realised he had survived the murderous Stalin.