Four decades after independence from Portugal, Angola remains a country with significant barriers to good governance and social development. Although the state’s constitution established a multiparty democracy in the early 1990s, measures of high poverty and low state provision of public goods, in addition to high levels of corruption from the Angolan executive government headed by President José Eduardo dos Santos, do not equate with the proclaimed status of a democracy. Through an analysis of Angola’s attempts at and challenges in democratization, particularly in the decade of the constitutional change (1990–2000), I attempt to explain why the government has remained largely authoritarian. What specific factors are most significant in the discrepancy between legal framework on paper and politics in practice? Why, in the terms of Ricardo Soares de Oliveira, has Angola become a “successful failed state”? By tracing a history of the parastatal Sonangol, the complex system of petrodollar patronage, and the attempts of the executive government to constrain civil society, I explain how the growth of the Angolan oil industry is most responsible for the failure of democratization. With special attention to the rise of Angola’s oil dependence, measured by total oil rents as a share of gross domestic product, I hypothesize that the country’s GDP growth during the 1990s (my independent variable) will produce opposite trends in its level of democracy (my dependent variable, using Polity scores).