Quality system, make poor recordings sound better?

I notice that as I move up the audio chain, poor CD recordings sound worse and the good ones sound superb, should this be the case? Also I on any given day my system sounds different even with the same CDs. Any thoughts on this as well?
IMO, the ultimate goal is to find a combination of components that allows one to enjoy as many discs as possible, price be damned. Those of us who have been in this hobby long enough know this!
Most of my music I listen to these days is from early and second half of last century so you would say why to use high end system for it? but let me tell you that only the best system will allow you to really appreciate the music which was archived then for us......
It may not be the recording, but the mastering. At least on vinyl (I can't speak to CD or digital formats), I can play some standard reissue of an old pop album that sounds flat and lifeless; but find the right early pressing and even if the original recording has its warts and limitations, you get the breath of life in it that doesn't exist in the mediocre remaster/reissue. These differences are not subtle and involve no 'golden ears' beard stroking contemplation. The differences are pronounced and readily apparent. That then means that you have to research the best pressings, or buy a bunch of them and make that determination for yourself. I have to assume the same issue exists with CD/digital formats.
I'm at a point where I'm in it for the music, not for the sonics- but that said, I still seek out the best pressings of the music I'm interested in. It may not make as much difference for newly released material where the recording started in the digital domain, a lot of dynamic compression was used, and there isn't a wide range of options for different masterings. But, certainly for older stuff, there can literally be hundreds of different versions of a popular recording, issued at different times, from different places (both within a given country and across the world).
Some recordings just didn't start out that great to begin with, so even the best versions (on vinyl) have their limitations. I don't mind that, though I hear the shortcomings. But, there is some distance you can go to improve the source material that has nothing to do with the gear, once your system reaches a level of 'good.'
There are certainly numerous ways a recording can be of poor quality, especially with digital recordings. If the recording is suffering from excessive Dynamic Range Compression, which is very common with modern pop recordings and even remastering of older rock recordings in particular, then the damage is done and there is no "high fidelity" to be found and reproduced. These recordings typically are more enjoyable via low fidelity systems such as ipods and car stereos.

Much of todays music is engineered for inferior playback systems and not intended to be listened thru systems like the ones most of us attempt to assemble.

This is much less of an issue with Classical music and boutique labels such as Telarc, Mobile Fidelity and the like.