For many centuries and in many cultures, jesters recited tales of heroic exploits, but they did more than simply recount past events--they amused, cajoled, and spun tales that transported listeners to the edge of mysterious, unmapped territories. Through the transformative power of play and the imagination, they reworked what was already understood and created from it new realities that transcended the established order. The author maintains that such imaginative play is vital to creativity in any medium and is fundamental for optimal human development. She explores possibilities for cultivating creativity through the playful, paradoxical stance of the jester--a serendipitous and purposeful, strange and familiar, disruptive and productive figure. Her discussion, grounded in a visual-arts practice that leverages uncertainty and randomness, considers the role of play in light of its wider implications for knowledge and creativity. (Contains 17 notes.)