In "Teaching Critical Thinking," bell hooks (2010) addresses education as the practice of freedom by explaining that we use "our intellect and our imaginations to forge new and liberatory ways of knowing, thinking, and being, to work for change" (p. 170). Speaking to the arts, Maxine Greene (1995) said that "of all our cognitive capacities, imagination is the one that permits us to give credence to alternative realities" by opening up new social spheres for engagement (p. 3). This coauthored article expands on the educational imagination using learnings from culturally sustaining pedagogies. Specifically, we address the importance of funds of knowledge and lived experiences as a way to reimagine art education. In so doing, we hope to contribute to a better understanding of what it means to engage in educational transformation in the arts.