I don't know if anyone can relate to this, but sometimes I'll hear an old pop tune from the 70's or 80's over a crackly speaker in a deli, or AM radio, or from a distant car stereo and I'll think boy, that's a great sounding tune and I'm going to dig it out when I get home. 
 
So I get home and fire up Spotify to listen to it in 320kbps technicolor and guess what? I don't enjoy it half as much in high quality over my good quality monitors or headphones. Why is this? The obvious answer is that hearing it on a crappy speaker or through AM radio evokes stronger memories as that's how I invariably heard it when I was a kid. But I'm also thinking there may be something in the idea that hearing a song in monophonic lo-fi throws the spotlight on the actual song rather than the production. You're not distracted by the immersion in a stereophonic wonderland - it's just bass, drums, guitar, keyboards and vocal fused into single stream of one dimensional audio. Maybe I need to rethink my whole mixing philosophy 

Or it could be that songs were mixed for optimum sound when played on equipment available at the time. I think the old radio stations used less normalization than is current practice, so that might be an issue. And a song that is mixed to sound really good on a 2 inch speaker may be too much on an audiophile outfit or home theater simulated surround sound. Or maybe music just sounds better when crunching pickles.

I like to listen to the Beatles in mono. I think the stereo releases sound like ****e.

My opinion... it's the fact all our new fangled gear is over accentuating the bass on everything to placate the dance/hip hop pop crud that's infected the industry.
 
Don't get me wrong... I love GOOD dance and GOOD hip hop and like listening to it through a system capable of ball rattling, bowel churning epicness.... but that low rumble is a relatively new thing in audio production (and the playback equipment).
 
Turn off your sub woofer or put it through a system that is era consistent and I bet it'll sound way better.
 
 
In fact... could you tell my neighbors to turn off their sub woofers while you're at it? Fookin' things should be banned in apartment buildings. lol...
 
 
Of course you've likely got flat freq monitors/headphones too which would probably get rid of that low end crap naturally but also accentuate the flaws in the recordings of the time (which would sound better through a stereo system of the time).
 
I know you've got a VRM Box and maybe this is a stupid suggestion (but I've been tempted to try it myself) is run your monitors out of it (with a Y splitter) to get the speaker emulation. Of course you get the room emu too which would likely ruin the whole thing but yanno... simulated speakers anyway.
 
Really though I think all new equipment should have "I'm listening to ball rattling modern dance stuff" and "I'm listening to ANYTHING else" settings.
 
That sub bass shiz started in dance halls where you couldn't hear anything else except the rattling sub bass. Now it's expected to be in our homes (and pissing off our cranky old neighbors). Now EVERYTHING has to be mixed that way and it's annoying.
 
Meh.
 
Hi, sharke. ;-)

A lot of the pop music from the 60's was recorded and mixed to sound good on the radio, with the vocal way up, and the bass and drums way down. I used to listen to Beach Boy records and I couldn't hear Brian's bass parts.

For me the question is: why do I prefer to listen to old hits, period. :P
 
TBH, I listen to the Beatles, Elvis and old Charlie Christian on my studio monitors all the time, and I don't think I enjoy them any less. Obviously, that set-up is quite flat. But that's how I like music.
 
That being said, there's obviously some kind of knee jerk reaction upon hearing those old albums the way I used to hear them, on a cheap turntable or even AM radio. Warm and fuzzy feeling all around.
 
I heard Hound Dog yesterday at Home Goods, and my mood sensibly switched. I went from impatient/anxious to be done running errands to just enjoying myself. In a similar situation, a hit from the last 10-15 years would have me boiling... The poor quality speakers would have rendered things worst, if at all possible.
 
Though, come to think of it, maybe not. Putting up with the excessive bass and high frequencies requires yet more mental energy. 
 
Modern mixes and modern aesthetics, both auditive and visual, are basically, more often than not, a relentless agression on the senses as far as I'm concerned. It's like they filter out the essential to be able to bring you more of what should be mere dressing... I guess audio equipment is designed to allow just that, too.
 
 
 

maybe those songs are just better?
 

I'm ashamed to say, I've started listening to AM radio in my car, on the oldie's station. When I'm driving around at night I listen to those old radio programs from the 40's.
 
I am sooooo past it. 

It might be because those oldies were actually...er...songs and not just self cheering (rap, hip hop, etc.) phrases and non-sequiturs ( i.e. I'm So Fancy, I'm Madonna ****, etc.) or random machine derived arppegiations (EDM, etc.)

Or not.

I do believe some people are writing and performing some very good music these days, regardless of how much I hate the production values.
 
Yet, to me, the sweetest sounding pop music was released in the mid-late 70's.
 
One album I'm obsessed with sonically is the soundtrack to Rocky 2. It's so smooth and glowing - like honey for the ears. Seems that from 78 on, post Van Halen 1, music production for the genres I like started changing drastically. I love lots of it, but something was lost.
 
I prefer to develop a stronger relation with material that I really like than to constantly search for new music. It seems odd to me to think that hundreds of thousands of artists can pour out millions of songs year after year and remain relevant, especially in a genre as formula-driven and simplistic as popular music.