First, I wanna say that colorism does exist in music no doubt. I will even go as far to say that mixed rappers are the new buffer class, before the industry goes full white, but in Wale's case alot of things are questionable.
I say that because you got cats like Ross...not only is he the same complexion as Wale, but was fat as fuck . Instead of complaining about what he was not, he took his weak points and made them his strong points, similar to what Biggie did back in the 90s. Hence the line "Big Black nigga in a icey watch".
When you exude true confidence and you are great at what you do, people will believe in you....no matter what you look like, they will believe in you. For example, MF Doom has been killing the game for years (in his genre of rap). Although he is not a mainstream celeb, he has a niche of followers that support him worldwide.
There are other variables too to take in consideration. We dont know what Drake, Kendrick and the rest of these cats are doing in those office meetings with those old white men, to get their budget money...ijs