How does inequality influence democracy in East Asia? This study attempts to find tentative answers to this question by applying theoretical frameworks of recent influential works in comparative political economy to four East Asian countries since the 1960s. The study tests for their applicability to these four East Asian cases not only Acemoglu and Robinson’s (AR) curvilinear relationship theory and Boix’ negative relationship of inequality with democratisation, but also examines Ansell and Samuels’ (AS) elite-competition theory that proposes a positive association of inequality with democratisation. The study, based on qualitative comparative-historical assessments of the inequality-democracy linkages in these four cases, finds that both the AR and the Boix frameworks have some validity, but they do not fully account for cross-case or within-country, time-wise variations, while the AS framework is the least convincing. Quantitative regression analysis confirms Boix’ argument that low inequality provides the best environment for democratisation, while high inequality deters it. Overall, the study reaches the conclusion that existing frameworks of inequality-democracy relations cannot offer satisfactory explanations for this conundrum, but should investigate “contentious” or “non-contentious” mobilisation and policy capacities of civic and labour leaders in their partisan involvement and social policy-making.