This interdisciplinary analysis presents an innovative examination of the nature of pride and humility, including all their slippery nuances and points of connection. By combining insights from artists like Aaron Douglas, Paul Cadmus, and Ambrogio Lorenzetti, literature like The Color Purple, Invisible Man, King Lear, and The Iliad, thinkers like Martin Buber, C.S. Lewis, David Foster Wallace, Martin Luther King, and Dante, and the lives of people like Dr. Alice Stewart and Harriet Tubman, this volume adapts a complementary rather than an oppositional approach to examine how pride and humility reinforce and inform one another. This method produces a robust, substantial, and meaningful description of these important concepts. The analysis considers key elements of pride and humility, including self-esteem and self-confidence, human interconnectedness, power’s function and limitations, and the role of fear.