What happens to the motley crew, that mobile, insurgent and 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? This dissertation explores the aesthetic and social experiments undertaken by the Trinidadian writer and political activist, C. L. R. James, and the Brazilian visual artist and counterculturalist, Hélio Oiticica, particularly those undertaken while each lived, at different points, undocumented and underground in the United States. It argues that while Linebaugh and Rediker insist the motley crew disappeared in the nineteenth century, James and Oiticica each independently find something like it in 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. James and Oiticica each sought to make contact with this aesthetic sociality. And they sought to expand upon such forms of contact during their sojourns in the United States. The dissertation examines, in particular, their attempts to generate and structure, in collaboration with others, new forms of contact, James through a new type of organization, the Correspondence group, and its organ, the Correspondence newspaper, and Oiticica, through a new type of environmental space, and the proposals for new projects or "programs in progress" he produced within them. It examines the way each tried to imagine new forms of writing that were to culminate in book-like projects they were unable to finish. It also examines the way sexuality articulated the forms of collaboration in which they were engaged, and the forms of production and reproduction, both textual and social, to which they aspired. This dissertation thinks the experiments James and Oiticica each undertook and the formations that developed around them as the traces of the motley crew, not the degraded remnants of a past phenomenon that was effectively crushed, but two attempts—among many others—at its reconstruction and renewal.