In what sequences have nations changed institutionally in history and does that order matter for later democratization? If so, are there historical-institutional pathways of “civilizations”? These previously neglected research problems are addressed in this paper on the basis of a new, unique, and enormous data set tracking all political institutions and systems in the world monthly since 1789. The aim is both empirical and theoretical: to take steps toward an understanding of the sequential aspects of political-institutional evolution. Results visualize sequences at regime level that show few signs of path dependency. They also show that democracy may emerge in all types of regimes, though at varying paces. Separating religious-majority nations, Muslim systems are less affected by democracy diffusion than other religious-majority nations. Muslim political systems also exhibit larger regime type unpredictability. Taken together with estimates of GDP per capita, majority religions explain a minor share of discrepancies between regime types: wealth of nations is more important than majority religion on a general, regime type diversity level. However, specifications of institutional details will have to be made in future research in this new area of historical political-institutional study.