Every dictator dislikes free media. Yet, many nondemocratic countries have partially free or almost free media. In this article, we develop a theory of media freedom in dictatorships and provide systematic statistical evidence in support of this theory. In our model, free media allow a dictator to provide incentives to bureaucrats and therefore to improve the quality of government. The importance of this benefit varies with the natural resource endowment. In resource-rich countries, bureaucratic incentives are less important for the dictator; hence, media freedom is less likely to emerge. Using panel data, we show that controlling for country fixed effects, media are less free in oil-rich economies, with the effect especially pronounced in nondemocratic regimes. These results are robust to model specification and the inclusion of various controls, including the level of economic development, democracy, country size, size of government, and others.