Agree that it could make an interesting article, Eric, partly because the bypassing you mentioned is still going on.
I'm not enough of a music historian to do that one, but if you are, you might start with country music's Zach Bryan. He amassed fans by releasing on YouTube songs like "American Heartbreak" before Warner Records signed him. Also in country, I'd suspect a lot of female artists are going the indie route because there's so much sexism in Nashville, they may have to do it.
By the way, if you'd like to write about music of any kind, the best place to do it on Medium is the Riff (if you aren't already writing for it). It covers a vast range of genres and has a highly engaged following and great editors in @kevinaalexander and @noahlevy. It has extras like a monthly album discussion group you can jump into between articles.
Kevin is also an editor of Everything Shortform, a good place to publish any 150-words you'd like to write. He and Greg, the other editor, publish VERY fast, so it's great if you've ever felt frustrated by the slow responses you can get from some editors on the platform.