Drake is just a “look at me” type of dude, so even when he’s trying to be above things he’s still doing it in a way that is meant for attention
Look at me, I’m vulnerable to my audience
Look at me, I’m a ladies man
Look at me, I’m rich and put my team on
Look at me, i beef with legends
It’s all on some Drake shyt. Even when he goes to a new sound it’s still Drake shyt. He is a blockbuster star with no gravitas. Any role he takes on, the character may be different but he always approaches it the same way. He will chameleon his accent when speaking but as far as rap goes you get the same Drake, no matter how street, Island, emotional, cool, etc the packaging is presented.
I was the first one in my circle giving Drake real rap props. But he never showed who he was beyond having skills and making some smart moves with his career. But the insecurity still reeks. That’s why his handlers have to defend him from criticism and he lashed out at Budden the way he did. Dispute with dialogue, don’t lash out like a Housewife
This is a good description, could it also be that, there isn't much more to him? Upper 'middle' class kid from Toronto, a child actor/theater kid, with an ego, who was never really struggling or street, in the post 2008 ways of hip hop, but saw enough and kept enough around him to write the raps. Someone who is sort of smart, and got an education in marketing/branding from corporate kingmakers who guided his rise, but isn't really an intellectual, or college graduate, or self educated guy. Someone who enjoys the luxuries of an A list star, but for whom survival and life or death was never really the drive behind his ambition, (like a Jay-Z) who likes sports and chasing women, and raps about it, with the ever present guidance, and knowledge of how to market, promote, and retain a market. and product.
Takeway is, when you compare him to the genre's other giants, his background is just less compelling, which made it
A) harder to get into the game and be respected
B) easier once he was in the game to be more relatable than say 50 Cent, who was the biggest star just 4 years before, this relataibility plus huge corporate backing, made him able to expand and amass a fan base
C) harder to be AS compelling to his fan base a decade plus in, who have largely moved on from the single/party lifestyle ennuni he channels, and celebrates, raps from a perspective on. It lacks urgency.
Same as you I was on his music early, a few of my boys say the first time they heard Drake was at my house, and they said I told them "This is going to be the next star", and even with an exceptionally good memory, I don't even remember saying that around late 2008/early 2009.