Sankofa, a prominent element of the Akan Adinkra system, is embedded in Jamaican Maroon worldviews as both a conduit to asserted Akan origins and a framework for self-definition. This paper treats Sankofa’s imperative—to look back, reclaim what was left behind, and use it to build a better future—as a lived philosophical orientation sounded, embodied, and transmitted through Maroon cultural traditions. Building on scholarship on Maroon political structures, histories of resistance, and expressive cultures, I examine the possibilities and limits of a Sankofa-informed approach to advancing Maroon cultural, political, and economic interests in the twenty-first century and beyond. Jamaican Maroons activate their historical archives through music and dance during annual treaty commemorations. However, fulfilling Sankofa’s mandate to “go back and get it” also requires sustained engagement with Jamaica’s less celebratory histories of fugitivity, freedom, victory, and betrayal. How might Sankofa instead be fully enacted through Maroon cultural traditions? Reading between the lines of Maroon songs about war, treaties, life, and death, I ask two questions: How do performances within state-sponsored national celebrations alter their meanings? And how do cultural icons function simultaneously as Jamaican Maroon historical traces and Jamaica’s nationalist symbols? I argue that using music and dance to promote a curated national memory can obscure and displace historical truths deemed disruptive. Nevertheless, the persisting unresolved tensions shape identities, fuel muted grievances, and complicate political claims that ultimately constrain Sankofa’s forward-facing transformative potential. I reveal how music is used to promote curated memory in the negotiation of difficult pasts.