I have been in this audio-fool journey for about couple of decades now. Most of my favorite songs/music/artists are from an era what we call now as poor recordings/bad dynamic range. I used to enjoy those music even when I hear it from the tea shop radio next street. As I moved up my gear, I started to find fault in them and started to reduce the time spend in such music. Started listening to more modern well recorded music. I started focusing on dynamics, sound stage etc etc. I moved forward in the same direction. In my current state, in such revealing system I have now, I started to enjoy the same old music which I blamed earlier for not having enough dynamics and poor recording. That surprised me.
So, the question is, as u move up in this journey, do you find older recordings are also enjoyable in high end system. Or do you think that is a myth. I don't want to discuss my gear as that is not the point of this thread.
The Subject line of your post is:
"Does the bad recording sounds good as well as you move up value chain"
But... in the concluding para of your post, you state: "So, the question is,
as u move up in this journey, do you find older recordings are also enjoyable in high end system."
To me the 2 statements / queries are quite different!
I will first respond to your Query in the Subject Line, viz:
"Does the bad recording sounds good as well as you move up value chain"
I have observed that there are Several recordings that sound "Bad".... congested and even dull, on a poor system. However when the same is placed on a good setup, what sounded congested, opens up as passages with complex detail and very good resolution.
Most albums by the Group
"The National" come under this category. Their album
High Violet is a favourite, and particularly the track "Sorrow"
So to summarise ... in some cases, what we assume to be a bad recording could well be a case of bad reproduction by a poor system. A better system will demonstrate the true quality of the recording. Such CDs can be used as a litmus test for a quick handle on on a system's capabilities.
There are also some very old recordings (1950s & Early 60s) that sound like simple old recordings on a mediocre system, but blossom with poise and reveal an old world simplicity and ambience when replayed via a Good system. This probably responds to your query in your concluding para