This article describes a lesson plan I designed to help students explore the complexity of Piers Plowman’s character both in Langland’s poem and beyond it. The lesson employs Piers’ appearances outside Langland’s text, specifically, in the letters written by participants of the Great Rising of 1381, and compares them to an unlikely parallel: World War II-era comic book covers featuring Superman’s fight against the Axis powers. Piers’ presence in the rebel letters and Superman’s comic book cover war efforts are not strict analogs, but they are provocatively similar instances of iconic fictional characters crossing over into historical events. Considering them together has helped my students see how Piers is not the flat religious character he often seems to them at first, but a rich, multivalent figure—one with a life beyond Langland’s poem.