This article extends an invitation to fellow civic engagement educators and others to reflect on how an eclectic and personal selection of great works of literature raises and illuminates some of the critical questions surrounding the concept and practice of civic engagement. Through literature we can explore the implications of various ideas and perspectives, often in situations that push values and worldviews to the extreme, enabling us to imagine how today's issues and circumstances might look if carried to their fullest extent. For each of the five works, this study offers a synopsis, relevance to today's issues, and questions for reflection and discussion.