This essay analyzes the various ways in which Queen Macoomeh's Tales from Icebox Land (2007) and selected poems of Mutabaruka represent the conditions of Caribbean immigrants in either Canada, England, and (or) the United States since the 1960s and 70s. The paper attempts to uncover the subversive, diasporic, and postcolonial qualities of pivotal West Indian literature that mainstream journals and scholars have neglected. In an attempt to reveal the intellectual and resistive nature of such literature, I place the two authors' writings in historical contexts which reveal the multifaceted experiences of expatriate West Indian populations who have fought hard for equality, citizenship, admissibility, and cultural space in Canada, England, and (or) the United States since the middle of the twentieth century.