Background and Objectives: There is a limited evidentiary base on the development of family medicine in different contexts and countries. The lack of evidence impedes our ability to compare and characterize family medicine models and identify areas of success that have led to the effective provision of care. This paper offers a comparative compilation and analysis of the development of family medicine training programs in seven countries: Brazil, Canada, Ethiopia, Haiti, Indonesia, Kenya, and Mali. Methods: Using qualitative case studies, this paper examines the process of developing family medicine programs, including enabling strategies and barriers, and shared lessons. An appreciative inquiry framework and complex adaptive systems thinking inform our qualitative study. Results: Committed partnerships, the contribution of champions, health policy, and adaptability were identified as key enablers in all seven case studies. The case studies further reveal that some enablers were more salient in certain contexts as compared to others, and that it is the interaction of enablers that is crucial for understanding how and why initiatives succeeded. The barriers that emerged across the seven case studies include: (1) resistance from other medical specialties, (2) lack of resources and capabilities, (3) difficulty in sustaining support of champions, and (4) challenges in brokering effective partnerships. Conclusions: A key insight from this study is that the implementation of family medicine is nonlinear, dynamic, and complex. The findings of this comparative analysis offer insights and strategies that can inform the design and development of family medicine programs elsewhere.