Using Kareem R. Muhammad’s definition of minstrel rap I will analyze the careers of rappers Drake and Trapo respectively. I argue that neoliberal principles encourage artist to “sell out” or embody characteristics beyond their own in order to achieve commercial success. Each artist will be assessed based on their content’s relevance to the original purposes of hip-hop music. I argue that Drake’s complicated career tells a story of a young artist grapples with neoliberal principles that pushed him to compromise the integrity of his music and the sincerity of his lyrics. On the other hand, I argue that Trapo’s career is a direct protest of those very neoliberal principles.