I get where you’re coming from. I tend to have to “click” with an artist/band before I can really sink into them. Sometimes it never happens.

That being said, I think the best approach to Prince is chronological. His oldest music tends to be the most accessible. As he developed, he got more experimental and that can make it harder to vibe with if you go in without familiarity.

I’d hit up the Wikipedia page and kind of surf through his first three albums. If you haven’t “gotten” what made him popular back then, then the best you’ll reach is appreciating his talent on an abstract level rather than feeling it. Nothing wrong with that at all, clicking with a given music segment or not doesn’t mean anything other than the fact that it doesn’t vibe for you.

But, he really was an amazing songwriter. So you could try browsing just his lyrics and see if that gets you into things that way. I know I’m not a musician in any way, so the subtleties of his guitar and other instrumental talent are beyond me, but I can comfortably say that he was capable of lyrics that could match any poet you wanted to point at. The craft of how he would structure a song is damn potent.

Even his bumping, club friendly stuff like Cream or Get Off is crafted extremely well. So if you’re into lyrics enough, that might be the path that makes him click for you