This chapter focuses on Hughes’s friendship with the Jamaican poet and dramatist Louise Bennett throughout the 1950s and ’60s. The chapter approaches their friendship by way of letters written by Hughes to Bennett, through Hughes’s discussion of Bennett in his correspondence with other Black male diasporic writers, and by examining his discussion of Bennett’s work in a 1955 article on transnational Black migration in the Chicago Defender. While Hughes’s response to Bennett’s work, particularly his consequent laughter, alludes to his convoluted relationship to diasporic women’s writing, these sources reveal how Bennett’s Jamaican and highly gendered folk poetry influenced Hughes’s understanding of transnational Black experience and identity. In addition, by orienting Bennett’s life and work transnationally through the lens of her relationship to Hughes, the chapter also attempts to shift discourse on her folk aesthetic beyond national and domestic frames. Among other things, doing so extends the parameters through which we can interpret humor’s function in Bennett’s embodied performance of Jamaican folk culture.