|Since the turn of the 20th century many writers, playwrights, and poets in Central America and the Hispanic Caribbean have published fantastic, gritty, and oftentimes unsettling stories of ghosts, anthropomorphic animals, zoomorphic humans, and uncanny spaces. These unexpected encounters and strange entities are an embodiment of muddled boundaries and a creation of unsettling and sometimes monstrous myths and fictions. Cultural theorists from Central America and Cuba have associated this kind of literature with a growing culture of disenchantment and cynicism that is rooted in the loss of utopian and egalitarian ideals associated with past revolutionary projects. Through the course of this dissertation, I look beyond cultural disenchantment as I show how many writers—especially women—from Central America (Guatemala, El Salvador, Honduras, Nicaragua, and Costa Rica) and the Hispanic Caribbean (Puerto Rico, Cuba, and the Dominican Republic) have utilized strange, fantastic, and sometimes grotesque elements in their work in order to imagine alternative, utopic futures that challenge gendered hierarchies in society. Traditional dualistic categories that require all-or-nothing identities (of being all good, all bad, all feminine, all masculine, etc.) are broken down in the literature that I explore from both regions. By joining sacred domestic spaces in uncanny environments, mixing the dead with the living, blending animals with humans, and rendering passive women into abject, erotic monsters—these (un)natural pairings contest and contradict naturalized gender and sexual hierarchies by revealing the fluidity of supposedly inherent and fixed boundaries. At the same time, the (un)natural pairings that I explore provide an unlikely and creative space where traditional gender and sexual ideologies are especially foregrounded, which invites the reader to rethink conventional and hierarchal structures of power, especially as they relate to gender in Hispanic Caribbean and Central American societies.