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?
phd
Knight- Dreamboat Annie on Mushroom records, which I think is a KenDun master is actually a great sounding record.
The Dreamboat Annie masters were excellent. Nautilus did what I think was the best pressing of that album. Still my go-to for demoing Rock bass resolution(the synth & drum/Fender bass doubling on Magic Man)
there's some very good and interesting responses here but it would be nice if there were a few paragraph breaks for some of the longer ones
Katy lied by steely dan is a great example concerning this thread. I have always liked Steely dan and heard many times that album has problems. I just didnt understand until recently.

I upgraded my speakers, preamp and amp in a relatively short time frame finally moving to a class a amp and a great preamp from Pass. This album sounds a lot different and not better but worse. Mid range and voices too high compared to highs and bass. I thought, well maybe its just the areas that my system now emphasizes but after listening to about 100 other albums, i now recognize what others have said about this particular album. other Dan albums are just wonderful.

I can only come to the conclusion, the resolution of my system is now revealing the weakness or issues.
11-07-14: Metman
there's some very good and interesting responses here but it would be nice if there were a few paragraph breaks for some of the longer ones.

Some folks do like to Ramble On. ;^)