Every dictator dislikes free media. Yet, many non-democratic countries have partially free or almost free media. In this paper, 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 non-democratic regimes. These results are robust to model specification and the inclusion of various controls, including economic development, democracy, country size, size of government, and others.