This chapter addresses key currents in Cuban poetry, on and off the island, from 1989 to 2020, a body of work rich in experimentalism and in dialogue with the coloquialista [conversationalist] poetics that characterized earlier postrevolutionary poetry. Synthesizing the work of numerous poets, the chapter demonstrates that, with the disillusionment that accompanied the disintegration of the Socialist Bloc, poets such as Marilyn Bobes, Soleida Ríos, and the influential and award-winning Reina María Rodríguez were at the forefront of antiheroic representations and of reinvigorating philosophical thought through their lyrical work. The chapter also explores the embrace of detotalization, deterritorialization, intertextuality, and hybridity, contributing to forms of radical rupture in the poetry of Juan Carlos Flores, Omar Pérez, and Legna Rodríguez Iglesias, as well as the postmodern strategies, reflections on the act of writing, and new identitarian sites found in the work of Caridad Atencio and the group of seven Black poets/creators calling themselves “El Palenque.”