This paper provides an overview of Singapore's inequality since 2000. Upon examining empirical indicators reflecting different aspects of inequality, there seems to be a divergence between largely stable macro-level trends and "felt" inequality experienced by citizens. While the empirical record reflects fairly stable income, wealth, consumption and intergenerational inequality, other data show how educational performance and sense of belonging are continuously tied to socio-economic position. Juxtaposing these insights against a qualitative analysis of Singapore's meritocracy, the social and political ferment on the issue of inequality in 2018—with heightened discourses among both elites and the public—makes sense against a backdrop of lived realities having become increasingly devolved from promises of equal opportunities. Typifying Singapore as a "pragmatic meritocracy" where systemic inequalities are recognized and addressed, the paper reviews policy responses to the rising discontent, and elaborates on the seeming disconnect between government narratives and generally incrementalistic solutions.