Many K-12 art teachers have rich artistic backgrounds and continue to be active as artists in spite of the challenges of time, energy, and stereotypes that insist a real artist would not teach. This article describes a research project that examined the educational dynamic engendered by teachers who are also artists. We interviewed and observed teachers to explore how teachers' personal artistry and artistic activities beyond school contributed to their teaching in school. It was clear that some teaching artists changed the educational dynamic of the classroom in ways that invigorated both the content and practice of teaching and learning. They cultivated complex learning environments that disrupted predictable approaches to schooling by creating unstructured and hospitable spaces characterized by play, conversation, and collaboration. (Contains 4 figures.)