© 2016 by the author; licensee Cogitatio (Lisbon, Portugal).Politics in democracy and dictatorship is markedly different; democracy and dictatorship are also associated with distinct policy outcomes. Do political regimes also select different leaders, i.e., do democratic leaders have distinct personal backgrounds to those of their peers in dictatorships, do they tend to hold different prior careers and posts while climbing the “greasy pole” of politics? The aim of this paper is to introduce the new data on leaders’ careers in democracy and dictatorship and compare their personal background, experience in politics, careers and significant posts prior to their tenure, and details about their time in office, inter alia. In general, democratic leaders differ from nondemocratic ones in terms of their educational, social and career background. The paper also finds significant differences among leaders in different nondemocratic regimes, and suggests possible venues for further research.