Sports can be used to facilitate analytical thinking when students are asked to critically conceptualize culture, societal institutions, and ways social capital is constructed within communities. In this article, the authors explore how one aspect of sports culture, pick-up sports, models democratic values. In analyzing the pickup game, as compared to sanctioned, organized sports, the authors provide ways in which teachers can help students to think about differing values within social (social capital), political (democracy), and economic (capitalism) ideologies. The authors also provide teaching suggestions through the use of two sports documentaries focused on the pick-up game, "Pelada" and "Doin' It in the Park: Pick-Up Basketball NYC."