I find this art history/rap history idea fascianting and I want to see it more fully explored in a book. You did the Spotify list now write me a book.
I see what you're getting at. ROC Marciano to me is like Kool G Raps flow slowed down and then mixed with a sort of It Was Written era obsession with designer clothes, yachts, Mafiosi, etc. All over beats that obviously evoke the Wu Tang.
Leaving aside all these influences though I just think his style is very enjoyable to listen to on headphones on the train. He's weaving these images together with rhyme patterns, and the images are often memorable and unexpected like talking about "three drops of olive oil in the wok".
But yes this is what underground hip hop is, in a way, this refusal or inability to tap into popular taste, and instead to be deliberately esoteric and introverted