The best explanation I can come up with for this guy's success is :
You have to consider what is the lowest common denominator woman. It's that poor to middle class demo of white trash skanks that listen to hip hop, watch the kardashians, know endless mainstream nonsense. Most of these girls are moderately to very overweight. They wear sweatpants and other whore wear. Their hair looks damp for some reason. They have no concept that tight clothes and tattoos make them look slutty. They dress only one or two steps above what you imagine a hooker looks like if they go out. They don't have any real idea of what upper classes are really like. The imgaine wealth as a black guy on a boat with a chain in a too large shirt a several hundred thousand dollars in jewelry.
I'm not 100% sure who Drake is, but when I google him his youtube vid has 185 million hits. These are the 60% of women that don't get a Bachelor's degree, and another 10% that get trash degrees.
They view dating a black guy that gives the illusion of wealth as high status because it's a way to compete with all of the other lowest common denominator whores they're friends with, they went to school with, they work with, etc.
This guy is simply regurgitating back at them all the celebrity imagery they've consumed. Add to that, that he looks completely unthreatening and you have mass appeal to basic bitches.