This chapter explores the rap debates of philosophical aesthetics, where early academic discourse on rap was at its most active. Rap aestheticians (led by Richard Shusterman) accentuated rap’s nature as an “art form”. The chapter examines the key issues within this debate, including the aesthetic experience of rap, flow (Mtume ya Salaam), the need for public support (and Herbert Grabes’ criticism of this position), and rap’s affinities with the Harlem Renaissance (Marvin Gladney). Rap’s engagement with other cultural practices, like driving and everyday culture, was discussed very early within philosophical aesthetics. Right from the beginning the debate was very international, with many of the authors coming from the Nordic Countries (Esa Sironen, Stefán Snaevarr, Martti Honkanen). It argues that there is still a lot to learn from aesthetic discussions on rap, and these philosophical debates are an interesting historical phenomenon, which rap scholars should know more about.