Rap, the musical element of hip hop culture, has depended on the recorded past to shape its birth, present and, potentially, its future. Founded on 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 material—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 this inter-stylistic synthesis? The article argues that in pursuing specific, stylistically determined sonic objectives, sample-based production facilitates an interactive typology of unique conditions for the composition, appropriation, and divergence of traditional musical forms, incubating era-defying genres that leverage the dynamics of this interaction. The musicological inquiry uses (auto)ethnography reflecting on professional creative practice, in order to investigate compositional problematics specific to the applied blues-hop context, theorize on the nature of inter-stylistic composition, and consider the effects of electronic mediation on genre transformation and stylistic morphing.