One of the challenges for health reform in Asia is the diverse set of socio-economic and political structures, and the related variability in the direction and pace of health systems and policy reform. This paper aims to make comparative observations and analysis of health policy reform in the context of historical change, and considers the implications of these findings for the practice of health policy analysis. We adopt an ecological model for analysis of policy development, whereby health systems are considered as dynamic social constructs shaped by changing political and social conditions. Utilizing historical, social scientific and health literature, timelines of health and history for five countries (Cambodia, Myanmar, Mongolia, North Korea and Timor Leste) are mapped over a 30-50 year period. The case studies compare and contrast key turning points in political and health policy history, and examines the manner in which these turning points sets the scene for the acting out of longer term health policy formation, particularly with regard to the managerial domains of health policy making. Findings illustrate that the direction of health policy reform is shaped by the character of political reform, with countries in the region being at variable stages of transition from monolithic and centralized administrations, towards more complex management arrangements characterized by a diversity of health providers, constituency interest and financing sources. The pace of reform is driven by a country's institutional capability to withstand and manage transition shocks of post conflict rehabilitation and emergence of liberal economic reforms in an altered governance context. These findings demonstrate that health policy analysis needs to be informed by a deeper understanding and questioning of the historical trajectory and political stance that sets the stage for the acting out of health policy formation, in order that health systems function optimally along their own historical pathways.