Gramsci’s vision of the national-popular and counter-hegemonic struggle offers an insightful framework for a more systematical and synthetic reading of the Bolivarian revolutionary process in Venezuela. In contradistinction to the simplistic accounts that draw on pure anti-capitalist and/or anti-imperialist struggles, a Gramscian lens can sharpen the perspective into internal colonial relationships with regard to squattering, race and gender as well as the contradictory nature of socialism. A Gramscian lens can also help us formulate a coherent critique of prevailing hegemonic leadership types from a participatory-democratic perspective. With this in mind, I contend that Chavez bequeathed two major legacies that need to be carefully taken into account by the revolutionaries and other socialist intellectuals and scholars of the twenty-first century. The first is that the task of the national-democratic revolution has become more pressing than ever for Third World revolutions and needs to be successfully incorporated into the struggle for socialism. Interestingly enough, this legacy brings to the table what Gramsci understands by the “national-popular.” Following Schiller’s (Dialect Anthropol 35(3):255–260, 2011) assertion that a comparative outlook on Venezuela is necessary in order to offer a more nuanced and sophisticated analysis of the complexity of the Bolivarian process, this paper also presents a comparative/historical analysis of Gramsci’s Italy and Venezuela. Chavez’s second legacy arises from the recognition that socialism is to be understood as a long protracted process replete with inner contradictions and risks embedded in the political-cultural transformation of daily life. This legacy underlines institutional innovation and cultural struggle, which exhibit astonishing similarities with Gramsci’s vision of counter-hegemonic struggle. As such, this paper touches on the challenges and contradictions of the post-Chavez era as they pertain to the transformation of daily life via counter-hegemonic tools and leadership mechanisms. Indeed, any genuine social transformation toward socialism excludes race- and gender-blind approaches, hence the necessity of rigorously analyzing the limitations of the Bolivarian process in race and gender relations.