Since the Ottawa Charter 25 years ago, community participation has been adopted worldwide by nation states and communities as a core health promotion strategy. Rising inequities since that time, however, have been largely unchecked in the Americas and globally, and have presented us with an acutely paradoxical time for community participation and action. On the one hand, transnational globalized markets and accompanying economic and environmental devastation have challenged the effectiveness of community action to create health. On the other hand, hopeful signs of local through national and international activism and of new mechanisms for community engagement continue to surface as meaningful and effective democratic acts. This article presents a dialogue on these issues between colleagues in the United States and Brazil, and considers the broader applicability to Latin America and worldwide. We begin by discussing how community participation and community organizing grew out of our respective histories. We consider the catalytic role of the Ottawa Charter in spurring a reorientation of health promotion and the genesis of healthy city and community initiatives, as well as other current community organizing strategies and the growth of participatory research/CBPR. We unpack the potential for co-optation of both community and social participation and end with recommendations for what we can do to maintain our integrity of belief in democratic social participation to promote improved health and health equity.