The notion that cultural characteristics influence political regimes remains popular, despite mixed supporting evidence. In particular, democracy is argued to emerge and thrive in countries where liberal or freedom-oriented values (so-called self-expression values) are widespread. Inglehart and Welzel, for instance, report such an effect, mainly drawing inferences from cross-country comparisons. Yet cross-country correlations between self-expression values and democracy could stem from different processes. Reinvestigating this relationship, this article finds no empirical support when employing models accounting for sample-selection bias, country-specific effects and the endogeneity of values to democracy. Self-expression values do not enhance democracy levels or democratization chances, and neither do they stabilize existing democracies. In contrast, this study finds indications that a country’s experience with democracy enhances self-expression values.