This dissertation analyzes symbolic and political discourse in the works of three controversial intellectuals who participate in the contemporary debate on nationalisms in Spain. Basque poet and essayist Jon Juaristi (b. 1951), after brief involvement in ETA during the late 1960s and early 1970s, evolved into one of Spain's most outspoken critics of Basque nationalism, a position that led to death threats from ETA and eventually his permanent abandonment of the region. After founding his theater company Els Joglars in 1962, Catalan playwright Albert Boadella (b. 1943) used it as a vehicle to fight the Francoist dictatorship and promote a Catalan nationalist agenda. However, he eventually reversed his position on the issue of Catalan and Spanish nationalisms and became a political enemy to many in his home region. Finally, Basque filmmaker Julio Medem (b. 1958) caused outrage throughout much of Spain in 2003 with a documentary film exploring the clash between Spanish and Basque identities. In my examination of Boadella's and Juaristi's autobiographies and Medem's documentary I explore the ways each author portrays himself as subverting, transgressing, or transcending the sub-state nationalisms that are virtually hegemonic in their regions, and I reveal how each author's treatment of gender, especially his representations of masculinity, either undermines or substantiates the purportedly "non-nationalist" position he stakes. I argue that Juaristi's and Boadella's restrictive, traditionalist gender constructions reveal conservative Spanish nationalist discourses which prevent them from surpassing the rigid power structures that nourish the opposition between Spain's center and periphery, while Medem's cinematic work does present the possibility of breaking free from the boundaries of the conflict of national identities through the transcendence of patriarchal nationalist symbolism - both Basque and Spanish.