In this article, the term teaching artist is reconsidered from a variety of angles. The ways in which the term teaching artist has developed, and the ways it remains nebulous, are explored. In this article, the notion that the teaching artist model presents an extension of the traditional master-apprentice model is presented. Observations are made about the pathways toward becoming a teaching artist and the systemic barriers to becoming a teaching artist are illustrated. Reconsideration is given to the professional developments available to teaching artists. Finally, the outcomes achieved by students of teaching artists are questioned and suggestions for research and policy are given.