Background: The Healthy Hawai'i Initiative was created in 2000 with tobacco settlement funds as a theory-based statewide effort to promote health-supporting environments through systems and policy change. Still active today, it is imbedded explicitly in a multi-sectoral, social ecological approach, effectively striving to build a culture of health before this was the name for such an ambitious effort. Methods: From interviews with key informants, we analyze two decades of the Healthy Hawai'i Initiative (HHI) in the context of the Robert Wood Johnson Foundation (RWJF) Culture of Health Action Framework (CHAF). We list HHI accomplishments and examine how the Initiative achieved notable policy and environmental changes supportive of population health. Results: The Healthy Hawai'i Initiative started with an elaborate concept-mapping process that resulted in a common vision about making "the healthy choice the easiest choice." Early on, the Initiative recognized that making health a shared value beyond the initial stakeholders required coalition and capacity building across a broad range of governmental and nonprofit actors. HHI coalitions were designed to promote grassroots mobilization and to link community leaders across sectors, and at their height, included over 500 members across all main islands of the state. Coalitions were particularly important for mobilizing rural communities. Additionally, the Initiative emphasized accessibility to public health data, published research, and evaluation reports, which strengthened the engagement to meet the shared vision and goals between diverse sector partners and HHI. Over the past two decades, HHI has capitalized on relationship building, data sharing, and storytelling to encourage a shared value of health among lawmakers, efforts which are believed to have led to the development of health policy champions. All of these factors combined, which centered on developing health as a shared value, have been fundamental to the success of the other three action areas of the CHAF over time. Conclusions: This evidence can provide critical insights for other communities at earlier stages of implementing broad, diverse, multifaceted system change and fills a key evidence gap around building a culture of health from a mature program in a notably multicultural state.