I have seen that, and in terms of the cringy stuff he does, it's definitely up there.

Here are my primarily unfiltered feelings about his music and persona:

I think at his worst, he's cringe, overly-self-indulgent, and pretentious. He needs a stylist because his hair sucks, his clothes are stupid, and he wears this fucking bear hat all the time that I hate. I hate hate hate people when people wear hats and it doesn't seem to serve a purpose beyond looking quirky. Take the fucking hat off, Jacob! He's the type that uses obscure words that you suspect he doesn't know the meaning of.

He also tends to be inappropriately maximalist—I'd point to his cover of Here Comes the Sun, Blackbird, Moon River (for which he won a Grammy!), and actually pretty much all of DJesse, a series of four (four!) albums. I don't really like the timbre of his voice; it's weird. I suspect he has like a perfect vocal technique or something, but as a result, it sounds completely removed from anything natural.

Unlike every other failed rich kid, he is legitimately talented, which you've acknowledged. I like some of his songs but wouldn't recommend them to anyone. His music feels like a technical demo in that many interesting, complex, and impressive things happen, which I like! But at my lowest points, I feel stupid when I listen to his stuff, even though he is musically speaking in a made-up language, and it's not my fault I don't understand it.

At his best, he seems genuinely open-hearted, with room to accept anything that comes his way. I do find some of his stuff inspiring! I like that a person like him exists and that many people look to him for inspiration and influence.

his face is annoying!

Specific to this point: I saw him live in concert for his Djesse Vol 1. tour and managed to meet him after the show. He seemed chill and it was a good chat. I took a picture with him, which I later put on my dating profile. Not seeing much success, I showed the profile to my friend to solicit feedback, and she said: "You should take that picture off because your friend is more attractive than you." I told her who he was but deleted the picture anyway.

He's not a monster (or not as much of one) like the rest of the people we look at over here. He's sheltered, and either there's someone in his camp pushing this kind of stuff, or there's no one to tell him that this tech is awful. Again, bad feelings!