What albums, in your opinion, sound unquestionably better on Vinyl rather than Digital?

All first pressings:

The Band - Songs From Big Pink
The  Band - The Band
Steely Dan (any)
Beatles - Abbey Road (EMI import)
Pink Floyd - Meddle (EMI import)
Pink Floyd - Wish You Were Here (EMI import)
Genesis (any up to including And Then There Were Three)
Michael Hedges - Aerial Boundaries
Beach Boys - Pet Sounds
The Who - Who's Next
The Who - Quadrophenia

I agree with Mr. "tooblue" statement. It's unquestionable that ALL albums sound better. Said so when CD's first hit the market. Most people (non-audiophiles) thought WOW! CD's sound much better! I personally thought they needed hearing therapy.

All Floyd.
All police.
All stones. 
All beach boys.
All sabbath. 
All Boston and journey. 
Pretty much every band that was established before digital. 

I've always understood that the analog recordings on vinyl and tape are 100% of the signal, subject only to the limitiations in quality of the recording equipment, mastering, and pressing of the recordings. 

While digital recordings are only a sampling of the analog signal (some lesser % of the complete signal), and are subject not only to the same limitiations of the analog recording, but also the drop outs of the incomplete signal of the sample.

So - it is not possible for any digitial recording to exceed the quality, or even equal the quality, of the analog signal of 100%. 

Now... the perceived sound of what you may hear on either format depends on many other factors, including the quality of your analog playback equipment.  So, it is possible that you may prefer the sound of a digitial format of the same recording, because it may have little of the recording artifacts (e.g. pops and clicks, tape hiss, etc.), and the engineer may have compensated for some of loss of the sound quality of the analog format.  

But... all things equal... with truly high quality analog playback equipment, analog format recordings should sound noticeably superior to digital formats.

bassdude....you are completely correct. So many factors come into play when comparing the quality of sound between digital and analog. When the digital explosion came about a few decades ago many were excited about the convenience and relatively low cost of playing the medium (CD's). I was also taken in by that innovation.

Today with so many advancements in digital playback with high quality DAC's, streaming, and others there has never been a more plentiful basket of options. Equipment has evolved so far from the original CD format. Sure, it's very convenient to play music in the digital medium for long listening sessions than to walk over to the turntable or tape machine to change more often than one would like.

The original post was to ask if the same recording would sound best with digital or analog. It would only be a fair comparison if the recording was played on the same system. But, this is where the comparison would be skewed on way or another.

A lot of people have equipment that can play both digital and analog. But most of those have systems and setups that would be more supportive of one over the other. Sounds like an experiment for someone with high quality setups with both. Then there's the human ear factor.

I have digital recordings that sound better than their analog counterparts. Mostly due to the age and use of vinyl. So......it's a comparison that can be only one to one. Plus the human factor.