This study investigates colonial, independence, and postcolonial moments to identify different modes of self-fashioning in the Jamaican landscape. It also explores the ways collective and individual senses of self, identity and sovereignty are perceived between the late nineteenth and twenty-first centuries. I assert that political processes involved in consolidating official national identities problematically reproduced hierarchies and exclusions reminiscent of the colonial period in politically independent contexts. In this regard, the cultural landscape serves multivalent purposes of proving grounds for visions of Jamaican national identity, counter-hegemonic articulations of those excluded from or marginalized by official notions of Jamaican national identity, and spaces for the invention of non-traditional modes of self-representation. I critique early nationalist projects through an examination of Sylvia Wynter's The Hills of Hebron and discuss the ways unacknowledged or unconsciously retained European cosmological elements undermine the sovereign identity they sought to construct. I also examine Michael Thelwell's The Harder they Come, Sistren's Lionheart Gal and Don Lett's film Dancehall Queen to discuss the marginalization of the working poor that persists within the newly independent relations of political power, and illustrate the ways modes of cultural self-fashioning like the ruud bwoy, or community theater emerge as spaces for negotiating self, identity, survival, and self-determination among the working class. I argue that the independence context is marked by exclusionary politics that provoke the development of more individual modes of self-fashioning, that vary between men and women, and also provide sites for counter-hegemonic discourses in opposition to nationalized discourses. Moving beyond the traditional framework of community based on heteronormative models, I examine Patricia Powell's A Small Gathering of Bones and The Pagoda to consider how queer communities are marginalized in nationalized discourses. I critique self-identity and self-fashioning within non-normative sexual communities in an analysis that traces gender and sexuality as indices of exclusionary patterns that are reproduced within nationalized identities throughout the country's history. This discussion argues that there is an institutionalized complicity between politics, culture, and religion in sustaining colonial power relations far beyond the colonial context.