This chapter explores the seam-line between education and art. Richard Anderson (Calliope's Sisters, 2004) writes in Calliope's Sisters: "Art is (1) culturally significant meaning, (2) skilfully encoded in an (3) affecting and sensuous medium" [my numbering]. This definition can operate as a practical framing for educational work with the contemporary arts. Breaking down these three elements, the chapter points out the questions and concerns of an educator that emerge from each element. Having clarified the issues and challenges in choosing art, explicating and interpreting art, and educating with the help of art, the chapter goes on to offer suggestions from the field as to successful strategies.