In this article, we show that large-scale macro-political change can powerfully condition how institutional practices shape individual cultural choice. We study the paired comparison of Portugal and Spain, two long-similar societies that moved from authoritarianism to democracy through divergent pathways in the 1970s. Data from the 2001 Eurobarometer indicate that while the cultural choices of persons born before democratic transition are comparable across the two cases, Portuguese youth born under democracy are substantially more omnivorous than their Spanish counterparts. We shed light on this puzzle through a structured, focused comparison. Our argument is that whereas revolution in Portugal overturned hierarchies in numerous social institutions and unleashed an ambitious program of cultural transformation, Spain’s consensus-oriented transition was largely limited to remaking political institutions. We show that this macro-political divergence resulted in a key cross-case difference at the institutional level. Whereas pedagogical practices in Portugal encourage young people to adopt the post-canonical, anti-hierarchical orientation toward aesthetics constitutive of the omnivorous orientation, corresponding practices in Spain restrict omnivorousness by instilling a hierarchical, largely canonical attitude toward cultural works.