In this paper we tell a story about how we partnered with a Chicago high school in order to turn the school inside out by displaying larger-than-life teacher portraits and statements at street level throughout the community. This paper explores how public art and activism can help teachers and students develop notions of civic literacy and engagement in order to change prevailing ideas about the role that teachers and schools play in our communities. Can teachers learn to relate effectively in communities outside of schools? Is this a desirable or even useful goal for educators? This paper examines notions of partnership, community, civic literacy and engagement, and the role that teachers and students might play in shaping their communities.