Rap, the musical element of Hip-Hop culture, has depended upon the ‘recorded’ past to shape its birth, present and, potentially, its future. Founded upon a sample-based methodology, the style’s perceived authenticity and sonic impact are largely attributed to the use of phonographic records, and the unique conditions offered by ‘composition’ within a sampling context. Yet, while the dependence on pre-existing recordings challenges traditional notions of authorship, it also results in unavoidable legal and financial implications for sampling composers who, increasingly, seek alternative ways to infuse the sample-based method with authentic content. But what are the challenges inherent in attempting to compose new content - inspired by traditional forms - while adhering to Rap’s unique sonic rationale, aesthetics and methodology? How does composing within a stylistic frame rooted in the past (i.e. the Blues) differ under the pursuit of contemporary sonics and methodological preferences (i.e. Hip-Hop’s sample-based process)? And what are the dynamics of the inter-stylistic synthesis? The emerging hypothesis of this paper is that the sonic objectives of sampling production create unique conditions for the composition, appropriation and, in turn, divergence of traditional musical forms, giving birth to era-defying genres, leveraging on the dynamics of this interaction. The musicological inquiry utilises (auto)ethnography reflecting on professional creative practice, in order to investigate compositional problematics specific to the applied Blues-Hop context, theorise on the nature of inter-stylistic composition, and consider the effects of electronic mediation on genre transformation and stylistic morphing.