The problem then is you're ranking the CREATION of the music, not the OUTPUT. You're judging the ARTIST, not the ART. And that's a vastly different animal. You're talking about praising the college junior vs the old dead scientist. I'm not talking about the men and situations BEHIND the creations, I'm talking about the creations THEMSELVES.
Let's say you find some guy who was born deaf but learns how to create harmonies by playing instruments in a sealed room and feeling how the vibrations interact. He builds instruments himself that maximize this effect and after 20 years of painstaking labor creates an instrumental album. Another guy is born privileged, goes to a private school, and is trained by classical musicians. He also creates an album that's just plain better than the first. Are you going to declare his inferior to the first because he didn't have to discover the scales on their own?
You might praise the first musician for his creativity and ingenuity, and marvel at his ability to learn and write melodies and harmonies without anyone teaching him, but that doesn't make what he did BETTER.
I judge music on its own, I judge artists on their context. The 90s were the superior decade because of the who/where/how. But that doesn't mean all the best albums are there. If you build me a car, I'm not giving you extra points because you had to invent the ICE yourself if the thing runs poorly. If you cook me a steak, I'm not going to ignore the shitty quality of the meat because you had to hunt and slaughter the cow yourself.