Following the chronological contours of Virgilio Piñera’s biography, this chapter explores his initial involvement with the Grupo Orígenes writers and his subsequent rejection of the group’s esthetics; his poetry, particularly his inventive long poem La isla en peso; his pioneering satirical and absurdist plays; the acerbic humor, nonconformist characters, and existential despair characterizing his short stories; the convention-shattering treatment of sexuality and homoeroticism in his novels; and his literary-journalistic writing. Noting Piñera’s enthusiastic initial embrace of the revolution and engagement in its artistic projects, the chapter also details his subsequent arrest, ostracism by the state, and censorship of his work until his death in 1979; the official Cuban resurrection of his legacy beginning in the 1980s; and international recognition of his work into the twenty-first century.