"Bridge Over Trouble Water" sounds artificial

I haven't listened to Simon &Garfunkel for a very long time for this very reason.It sounds better on a car radio.I need to pull the boxed set out and give it another try I guess.I've been trying for years to get my favorite 60s and 70s recordings to sound pleasing(if not fabulous) on my system.I've had to sacrifice some transparency and detail in order to thoroughly enjoy the old rock and blues that I love.There are always trade offs.

Remember the studio dubbed that song to havea  certain spatial, **oceanic* effect.. Sail of silver girl, sail on by,,,
so maybe with your upgardes, you might had the same exp i had listening to Diana Krall after adding a  new component/upgrades.
I could detect a  bit studio tweaking on Diana's voice ,,  a tad over dubbed.
anyway, so yeah, the Simon song now has lost that *old charm* *more organic* *monoish* flavor you remember from when we 1st heard that song wayyy back in 1971.
Your system back then did not have the same fq resolution you have now,,  the experience changes as the resolution becomes greater , ... take my LS9 preamp, modded with new M caps, Johnny Winter LIVE AND, sounded *raunchy*, ,  not like I recall back on my LP days with crappy equipment,.,,, Resolution was not near what I have now,, Then i gota  Jadis DPL modded with new M caps, and sure the raunchy, rawness was still there,,,but somehow ~~enjoyable vs the LS9's resoltion. The LS9 revealed thev studio sounds perfectly, but the Jadis DPL not only exposed the rawness, but added soundstage, making the cd much more listenable. 
So a preamp definetly  reveal whats on the cd, a  great preamp not only reveals, but also gives depth and resolutions. 
We had cheap sound systems back then, but not once did we say,,*man that Johnny Winter LIve Andlp sounds so *raunchy*. 
Now with high resolution components/mods, ,, our old favs,  are not going to have the same listening experience, Whether athst good or bad, depends on how we feel at that moment.
That song was magical when it 1st came out. and we loved it even on our Zenith consoles....

I haven't listened to Simon &Garfunkel for a very long time for this very reason.It sounds better on a car radio.I


I think, above,  I touched on what you are saying here. 
Simon and Garfunkle on our higher resolution systems is not going to bring us back to that magical moment we 1st had on our Zeinth consoles, /Marantz crappy ss amps. 

most of the recordings I enjoyed when I was younger, I can't listen to on digital.  I have to get vinyl to enjoy them.

Am I still the only one who feels that favorite songs sound their best on AM radio? Even classical. That will not help OP, but when the topic has been brushed against, I thought I'd ask.