Ireland's recent history is defined by the waning of long-powerful institutions, with membership in the European Union and the failure of the Catholic Church at the center of rapid economic and social change. Between 1990 and 2000, Ireland's standard of living jumped from the bottom tier of European countries to become the highest in the EU, while outward migration--a constant since the early nineteenth century--was reversed and Ireland began to draw Central European, African, and Asian immigrants. In short order, the same corrupt postcolonial governance, shortsighted policy, and widespread greed that drove the rise in the nation's fortunes (known popularly as the Celtic Tiger) helped bring about the stunning financial collapse of 2008. I focus on recent literary texts while examining economic, social, and institutional history, drawing upon performance, music, and film to identify a previously unrecorded literature of male anxiety and adaptation. Aggregating these disparate narratives illuminates broader debates over national identity and institutions in addition to gender and economics. Using the lens of hegemonic masculinities and social relations of gender, I examine texts that are both symptoms of and interventions in the legitimation of patriarchy. I concentrate on characters who attempt to adapt to new expectations of masculinity, but are nevertheless anxious about the erosion of male privilege or the assumption of new roles. Taking these characters as productively unreliable guides through this period of rapid change, I highlight the ways in which male privilege is continually reinscribed even as it is ostensibly challenged. In grouping depictions of land developers, entrepreneurs, rock stars, priests, queers, and soldiers, I unpack the rapid developments in and changing attitudes toward prosperity, modernity, clerical scandal, and revisions to national narratives. I then turn to a group of formal innovations in post-collapse theatre as a case study in techniques for resisting the reinscription facilitated by texts in the period of prosperity. Ultimately, I demonstrate that these texts and their negotiations of hegemonic masculinity provide a robust archive of the challenges the contemporary period presents to the performance of masculinity.