The racially tinged Confederate flag debate in South Carolina is viewed as a signifier of more popular struggles over the representation of "southern heritage" and under girds the social studies unit described in this paper. The unit was designed to teach the curriculum from a popular cultural, issues-oriented perspective using critical pedagogical techniques. Using the Confederate battle flag as an organizing theme, the unit's substantive components include critical and reflective exercises such as journaling, debating, writing essays, researching, and role-playing. Both traditional assessment strategies as well as alternative assessment strategies (e.g., portfolio development, free-writes, and performances) were used to determine students' learning and interests. The unit was taught in a conservative, rural, working-class, majority White, upstate South Carolina school setting. This approach enabled the students within the blue-collar population to think critically and reflectively about their own positions, privileges, attitudes, beliefs, and "heritages," as well as see that democracy in action is painful at times, messy, and even embarrassing, but necessary if society is to reach inclusive compromises.