Teaching artistry is indebted to Dr. Maxine Greene, who helped develop the field's collective wisdom during her 36-year term as Philosopher-in-Residence at Lincoln Center Institute for the Arts (in addition to serving on the editorial board of "Teaching Artist Journal"). As Professor Emeritus at Columbia University, Dr. Greene taught the class "Education and the Aesthetic Experience" every semester until her death (May 29, 2014, at the age of 96). Here Andrew Gaines reflects on the power, potential, and limits of teaching artistry based on existential philosophies of Maxine Greene and psychotherapy.