This article proposes revisions to the theory of political transitions by analyzing patterns of recent popular challenges to neopatrimonial rule in Africa. The approach is explicitly comparative, based on contrasts between Africa and the rest of the world and among regimes within Africa itself. Arguing against the prevalent view that transitions unfold unpredictably according to the contingent interplay of key political actors, the authors contend that the structure of the preexisting regime shapes the dynamics and sometimes even the outcomes of political transitions. They find that in contrast to transitions from corporatist regimes, transitions from neopatrimonial rule are likely to be driven by social protest, marked by struggles over patronage, and backed by emerging middle classes. Following Dahl, the authors compare African regimes on the basis of the degree of formal political participation and competition allowed. They find that regime variants—personal dictatorship, military oligarchy, plebiscitary one-party regime, and competitive one-party regime—are associated with distinctive transition dynamics. Whereas transitions from military oligarchies are typically managed from the top down and are relatively orderly, transitions from plebiscitary systems often occur discordantly through confrontational national conferences. A consolidated democracy is least likely to result from the abrupt collapse of a personal dictatorship and is most likely, though never guaranteed, from a graduated transition from a competitive one-party regime. In general, getting to democracy is problematic from all regimes that lack institutional traditions of political competition.