Gambino is an artist who potentially has a lot to say, is probably a pretty swell guy, and has a lot of eyes on him, but he can't express it right. His style is highly derivative and you can see the seams with nothing attached that feels unique despite him having a sort of unique personality. Listening to his music makes you feel like you'd rather listen to the 2-4 major influences of his instead, even Wayne. This is even weirder because I'm pretty sure his entire demographic grew up on Wayne, Ye, Drake, etc. Lyrically he can be cringeworthy, I've caught him biting punchlines from battle rap at times and he sounds unnatural when he starts spazzing on beats. He's a far more talented producer (in both the musical and presentation sense), singer and marketing genius than he is a rapper. Sometimes I feel he is a genuine guy who is just putting his thoughts out there, other times I feel it's very calculated including the comments about him wanting to be white. Sometimes I feel like his music and persona ends up feeling like a caricature of my generation or KTT-bait.
Ultimately, I'm not sure he's made a good case for why anyone should care or why he deserves a spot in the game. And considering as far as he's gotten in the game, that's a bit puzzling. Why should I listen to his Drake, Wayne, and/or Kanye impressions?