Notably, Simon and Garfunkel, are just simply superb. Their music is simple, and the range and timbre of the 'instruments' are so distinct I would think it difficult to not achieve a great rendering...other than crowd noise on the live recordings.
For the commentary on Clapton and Layla, as this was in the vinyl era. In that time period the 'fuzz' sound was also popular which extremely boosts the mid on guitars washing out male vocals and leaving strange artifacts. Additionally, in order to record Layla in particular, a tiny, tiny amp, 5W was pushed to 11, put in a soundproof box and mic'ed. The prefered material for guitar amp speakers is paper due to the break-up. Additionally, tube breakup is dominant and then oversaturating the microphone all combines to get a tone. This is common and in practice, most guitar recordings are mic'ed directly from the main amplifier and the guitar tone is completely overdriven several times...though today there are direct analog and digital routes and 'recording only' amps, but Layla was really pushing a tiny box, in a studio setting and the only thing 'listening' was a period quality microphone with everything at 11. Beautiful playing though.
Before CD and tape, many masterings were sonicly titled toward a vinyl release, even with the RIAA curve in play, bass was made subtle and the shimmer of cymbals was cut-off. Alot of that has to do with dry rooms and separations of drummers from the players as well as mic'ing vocals and playing separately. In a live situation you get an intermix of all harmonics, like a piano, but that does not appear in studio albums. Listen to any Madonna album and you'll 'see' her head floating around in space, in a booth, separate from all instruments because it was recorded that way. Just scary. Although the requirement to 'thicken' singer voices and create harmony from the group itself yielded the need to combine tracks which eventually muddied them so they forcefully muddied all the other instruments as well.
I believe in the vinyl/CD co-existence era, the engineers still targeted vinyl and FM as the destination so treble was high and bass was muted. This translated into horrible CDs....Genesis "Invisible Touch" is a great example of over treble zero bass whereby Rush (not-remastered) Signals is an example of how they thought they would tame brightness of digital but its just a muddy mess...but sounded okay on FM (since they stations FURTHER process the sound). Yet for Genesis "Duke", it sounded fantastic...vinyl and CD. Additionally, the later Rush albums overly embraced the dynamic range and frequency response of CD's ("Presto" forward) and are now just too much. 2112, Moving pictures, Grace Under Pressure and Power Windows seem to hover in the 'acceptable' range. In concert, Geddy would play 'dry' and that was a treat.
In terms of 'good' recordings, I think Roxette 'She's got the look' is a good example of modern separation that is friendly to all media. I hate the song. Also, 'Good' by Ezra....but they produced that album themselves. These are just sonic examples of the distinctness, dynamics and range, seemingly put correctly on a final product. Not endorsing Roxette at all.
R.E.M., especially early, sounded best only on CrO2 tape for some reason. And you have to contend with the fact that Michael Stipe always though lyrics were 'trite' hence liner notes and lyrics only started appearing later...and why he mumbled most of everything until 'Document'.
U2 Joshua Tree MFSL CD is fine, but strangely that concert live in '88 or whenever sounded better than the CD. The bass extension was much better and was snappier renderings....although, "God's country" sounded great on CD when I was in my 20's....hmmm. Not so much today.
The Rolling Stones always needed that 'sound' and everything was mushed through their hearing. It always sounded like they recorded everything in the same room with one take. Charlie Watts is the best though no matter how poor the recording. So swingin'...always. And opposite to the Beatles, they are a road band and nearly have more compilations than actual albums. So, I don't think they gave everything much thought other than capturing the 'essence' and Mick Jagger I've been told did not like alternate takes floating around or being considered.
Maybe fourthly, Phil Spector was an example of a producer [and these guys MAKE the sound what it is] who always wanted a 'sound' so everything was squeezed through that...the wall of sound...the session musicians contributions... Other unrelated artists were subjected to the same 'filter'...the Beach Boys...the Who (prior to It's Hard album). For complete and domineering "producer control" Phil and others knew the sonic importance of separate rooms, loops of some details...e.g. sounds for cymbals, especially present on Ramones recordings....Blitzkrieg Pop is a perfect example. It's the sound of 30 seconds of actual performing set to loops/cuts for the backing.
Fifthly, food for thought, but there is other smaller points of interest, but the people making the 'recordings' of the artists are usually the top industry professionals, ALWAYS MEN, and as such they are usually 45+ in years...the sound engineers I've researched were 50+ in age...despite protestations that they still retain perfect hearing. Men after 45 can no longer hear the frequency dynamics that you would want in a recording. It's medical fact. Especially with regard to hearing protection was nil until around the 1990's...so reference level sessions blew out ears on a daily basis. Yes, older men can afford the best equipment [now], but the sound artifacts that made the music sparkle are gone....even those that were heard on a poor quality car stereo. If you ever take a hearing test, even the free computer hearing tests and have a 12-year old nearby you'll be horrified. You'll play with tones 13 khz, 14, 15, 16, and 17 khz (even though 19 khz) changing the volume, sliding the frequencies around and around, not hearing a thing and a twelve year old will ask you if you were trying to play a song that sounded horrible and can you stop. Even though you heard nothing. Then ask them to face away and do the same thing. They can hear all the detail you can't. It's just scary.
As a qualifier, I own many of the modern and vintage instruments involved in maybe 40% of the songs from the 80's to 90's, regarding keyboards and guitars, including the amps and processors. I guess a piano spans all time though. The Fenders, some Boogie's, the popular Yamaha and Roland synths and some of the drum machines. Having digitally recorded 'the real thing' at home and comparing to the recordings of the popular songs, especially with synths (many stock sounds were and still are used)...the recordings out there are all over the place once they have been processed and compressed to ensure only the studio has the best quality version. And, without all the malicious intervention in the songs how they were and when they were recorded, I don't think they would have been edgy, grungy or loud enough to become popular...which is how we heard them in the first place. They had to sound good on FM or else.
For Bruce Springteen, they just have too many 'stars' and too many instruments all competing the same space. Their simpler songs sound fine "I'm on Fire" and "Brilliant Disguise" for example...everything else is just too layered, too think and too synth.
As a side note to classical, the advent of digital ruined all recordings for DG in the mid 1980's and I haven't purchased anything non-vinyl classical except for Phillips or Sony label since. And there were all those $3 discs that were garbage. Such a waste but the recordings were just horrible and you'd get some trio or quartet that happened to be in the bar that day as well. It cheapened the recording process and got me stuck in a loop of classical for whatever I played myself or whatever vinyl I still had. Too many spit valves, audible mumurs, moving music stands around. It took a while for them to figure out that all that was being picked up. So Issac Stern live, again, was still better than anything recorded. Simple and pure.
BTW, I believe Weather Report, Heavy Weather is a solid rendition on CD due to some really great dynamic range.