What happened to “the motley crew,” the mobile, insurgent, creative social formation, crossing racial, gender and generational lines, that historians Peter Linebaugh and Marcus Rediker identify as a crucial counterforce within the consolidation of capitalism, imperialism, and the modern state? I address that question by way of the twentieth-century aesthetic experiments undertaken by the Trinidadian writer and political activist C. L. R. James and the Brazilian visual artist and counterculturalist Hélio Oiticica. While Linebaugh and Rediker insist the motley crew disappeared in the nineteenth century, I argue that both James and Oiticica independently discovered its active remains in what I call “the aesthetic sociality of blackness,” the popular practices they encountered among the predominantly black residents of the barrack-yards of Port of Spain and the favelas of Rio de Janeiro. These experiments are marked by the claims they make on that sociality and the claims it makes on them. James’s novel Minty Alley and the banners/tents/capes that were the starting point for Oiticica’s Parangolé explore the creative practices they encountered in autonomously organized performative modes like cricket and samba and the forms of speech, gesture, shelter and adornment conventionally understood to embody “informal” social life. I examine the ways James’s and Oiticica’s claims take shape in these early works and the way the counterclaim of that aesthetic sociality irrupts into and rearranges these works, using them as vehicles for its own expression, which can be contained neither by the works themselves nor by the gesture (or the analytic) of appropriation.