This chapter offers a condensed history of the relation between jazz and hip-hop. Framing the argument with reference to poet-activist Amiri Baraka’s 1967 essay “The Changing Same” and 1972 album It’s Nation Time, it examines the development of “jazz rap” and the use of direct references to jazz in “Golden Age” hip-hop. During this period, the chapter argues, jazz’s ambivalent position within hip-hop reflects the political ambivalence of the post-Fordist era and the defeat of the revolutionary aspirations of the 1960s, an ambivalence musically indexed in the melancholic use of jazz samples in records made in the immediately after the Golden Age. The chapter concludes by suggesting ways in which contemporary hip-hop and jazz might maintain an underground ethos closer to the radical political edge that Baraka saw in free jazz: noisy, disjunctive, experimental, and focused on change.