Somewhere between like Rocky and Cosby

from Macklemore and Ryan Lewis (Ft. Ray Dalton) – Can't Hold Us Lyrics on Rap Genius

Meaning

His style is between determined (Rocky) and comedic (Cosby); the Cosby reference transitions well into the next line.

This reference is one of many biracial references Macklemore makes about himself because he’s a white rapper in a predominantly Black art of hiphop. Here’s another example

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