The path of Cuba’s cultural economy and patrimony deviated substantially during the “Special Period in the Time of Peace” (1991-1999), including the collapse of state sponsorship for the arts and the opening of the Cuban economy to foreign investment. This opening was slight but significant. Artists found themselves in a position where their work no longer solely existed as patrimony of the state but as personal methods of success and survival. My dissertation analyzes how three Black Cuban artists, René Peña, Belkis Ayón, and Elio Rodríguez, engineer and manipulate self-portraiture as a critical tool through which they can explore issues of belonging and place in connection to the Cuban national project. I attest that each artist positions representations of themselves, or their avatars, within their work to examine what it means to be Cuban, Black, and human. I begin my project by establishing how the figure of the White, hyper-masculine man has served as the ideal Cuban citizen following the revolution and independence. Cuban artists have explored themes of national identity and belonging since the mid-nineteenth century, in many instances reflecting on race and the presence of African descendants in Cuban society. The continued discourse on “racelessness” and the supposed eradication of racism in the country made the potential to be both Black and Cuban impossible. Official discourses on race after the 1959 revolution attempted to erase, and in many senses, whitewash, the historical legacy of racism in Cuba through the expressly public abolishment of discrimination and difference in Cuban society. An attempt to erase all forms of difference, or the visibility of difference, within Cuban society accompanied advances in equal opportunity to jobs, education, and housing for the Black Cuban community after the revolution. My project focuses on how Peña, Ayón, and Rodriguez contest the long-established hierarchy of race and gender in official cubanía [Cubanness] through visual discourses. I argue that the works of Peña, Ayón, and Rodríguez are not examples of a hybrid, creolized synthesis but instead working products of investigation and play. Considering identity as a process and project always in flux, I contend that these three artists use aesthetic strategies to represent Cubanness and Blackness as not mutually exclusive but simultaneously iterative and dynamic. Considering their artistic practices as performances of Blackness and self, I present these artists as critical interlocutors of the cultural moment. I argue that Peña, Rodríguez, and Ayón mobilize the Afro-diasporic conception of the self as external and multiple through their avatars as a form of self-fashioning. An avatar functions as a proxy for a person, acting as an extension of their self, traversing locations and discourses otherwise inaccessible to the primary self. Avatars blur the boundaries between the material and the virtual world and muddle the distinctions between subject and object, flesh and body. Peña, Rodríguez, and Ayón create portraits of their “other selves” to assert their subjectivity and personhood in realms that otherwise negate their presence. Through a close visual analysis of the work created by Peña, Ayón, and Rodríguez, I show how their use of alter-egos elucidates their experiences of the materiality of Blackness and the multiplicity of being. I argue that this is mainly present in the material processes inherent in the print-making and performative productions included in each. For example, in terms of color, Peña and Ayón use black and white critically, manipulating the various gray scales between the two tones to illustrate the many potentialities of cubanía. Rodríguez has interestingly moved into soft sculptural forms of blacks and whites, but the works discussed here use fixed colors to create a humorous play with traditional Cuban aesthetics. Each artist uses color differently, but through their processes, they imbue their works with a sense of materiality and personhood that is only possible through print. For these artists, the work’s creation becomes a performance of self-definition that parallels the many ways we perform race, nationhood, and belonging.