Leadership succession marks a truly ubiquitous phenomenon with manifold and wide-ranging implications, which explains the major attention that issues of succession have received in the international literature. Most contributions to the field continue, however, to focus on political succession in either democratic or non-democratic regimes. This article develops an integrated perspective on key aspects of leadership succession at the level of political chief executives in democracies and autocracies. A comparative assessment across time and space reveals several features that challenge established notions, and stereotypes, of leadership succession in democratic and autocratic regimes. The empirical ambivalences identified suggest that the way leaders come to and fall from power should be made a more explicit part of conceptualisations of political regimes, and comparative evaluations of their respective democratic quality.