This article studies the digital-cultural labor of three Cuban Instagram comedians and the worldmaking they promote. The comedians, Marlon, Chupetin, and Kende, immensely popular among Cuban audiences, create content that centers their Black working-class and street-smart identity. Through a close analysis of how these comedians utilize performance as rhetorical tools, I examine the entanglements and possibilities that marginalized content creators face when making symbolic and embodied meaning not sanctioned by the nation-state's meta-narratives of normative identity. I draw on theories of performance studies, media anthropology and Caribbean studies, to conceptualize the political, cultural, and personal stakes that come with the ‘world-making’ labor of Cuban Instagram comedians. I argue performances of estranged ways of being, distributed through transnational digital networks, enact aspirations of redressing long-standing desires and anxieties about national identity and personal agency. Ultimately this article situates social media platforms as vital spaces of worldmaking in a digital era.