Toro y Moi | Childish Gambino
Potentially the most likely collaboration on our list is Toro y Moi (Chaz Bundick) and Childish Gambino (Donald Glover). Not only do these two bear a strong resemblance to each other but they both represent the community of black nerds out there. Also they both are multi-talented, as Chaz sings, writes and produces in different genres (and even dips his toes in directing), while Glover sings, raps, produces, writes, does stand up and acts. With Toro y Moi having many fans in the rap game, such as Tyler the Creator and Chance the Rapper, this collaboration just may happen in our lifetime.