Why Does All Music Sound the Same; An Explanation

Judicious use of compression isn’t a bad thing. George Peckham, whose masterings are sought after (Porky, Pecko, etc.) used a classic Fairchild tube compressor as part of the mastering chain to juice the recordings he was mastering.
To me, music is about building tension, reaching a crescendo and releasing it. That’s true of classical music and of much ’classic rock’: think about the anthemic songs such as "Stairway," or "Freebird" or "Hotel" (yeah, I know, but they got overplayed for a reason and it wasn’t just marketing). Each of those songs has softer acoustic passages that built to a heavier, darker sound; the joy is in the contrast as well as the build up, knowing that things were going to get louder, harder and more pounding. (no sexual entendres here but ’rock and roll’ is itself a euphemism for the act).
I like a lot of ’psych-folk’ because it is a study in contrasts. I don’t think jazz fits into this model, but I haven’t thought that one through. (too many different styles of jazz for me to get my head around as I write this).
Highly recommended for a study in contrast is Roy Harper’s "The Same Old Rock" from the album, Stormcock. It is a virtual textbook of contrasts, of one style of playing morphing into another. It didn’t hurt that Jimmy Page played acoustic guitar on this track.

Judicious use of compression, absolutely good; George Peckham and Bernie Grundmann good; saturating limiters bad.

I don't go to live music in small venues anymore, seems people just want it loud, distortion be damned. I saw Tedeschi Trucks band at U of Missouri a few years ago. Large Music dept btw. The opening act was good, excellent sound. The T Trucks band was loud and at least 50% distortion. I walked out but seemed like I was the only one who cared. I lived in LA for a few years and it was better but not great. I went to scores of rock concerts when I was young, scores of years ago and never heard bad sound like this. I saw Lynyrd Skynyrd on their first tour and they were underpowered but not distorted. They opened for ZZTop who weren't.

Interesting subject.

As someone who has moved from an analogue realm to a digital one in my work, I can see how the "highly measurable" numbers game has become of "importance".  Remember the show "Max Headroom"?

When I had to make the switch from film to digital, I was all concerned about the "numbers". Then there was a job that came along that caused me to through all the math out the window and trust my eyes - as I had been doing for decades prior.

Lowest common denominator = biggest market

I can remember being at the TSO watching a performance of Beethoven's 9th. I found it to be lacking in impact - dynamics. This until, Ode to Joy happened. And I realized the conductor had left something in the bag. Realizing the limitations of the hall, and the size of the choir, he left room for the moment of "impact". Granted the only reference I had to this was the Karajan two symphony, double choir recording. No shortage of range there should you want it.

I also remember seeing a documentary on a painter who always mixed white into every color. So, if he needed more red, he has it. Bore blue... You get it.

The secret I think is to not put white in everything and forget that there is still more color to be had.

Depeche Mode has always felt like that for me. All of it running at the same intensity. Mr Bungle on the other hand - not the case.

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I confess I never really managed to work up much aggression about the loudness war. Frankly sometimes it can be a bit of a pain when you are listening to classical and have to keep dicking about with the volume to be able to listen to the quiet bits then not get your head blown off 4 bars later. So, at least for me, more dynamic range is not necessarily more better.
Also we tend to forget that popular music has always been cookie cutter stuff. In the UK the legenday production team Stock, Aitkin and Waterman just hashed out much the same stuff for an endless stream of young look-a-likes and regularly hit the top of the charts in the 80s. 20, 30, 40 years on we just remember the stuff that was good enough to last, whereas in the present we hear all the only-of-the-moment crud as well.  On a slightly seperate note I am reminded of the old pub game of getting people to hum the theme songs of Superman, Star Wars and Indian Jones back to back and watch them struggle because actually they are very, very similar.