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This paper explores the effects of transgression in teaching caused by the operation of new media. Adapting Bell Hook’s argument on ‘teaching to transgress’ that articulates the necessity of freedom for the learning experience, the paper proceeds to critically examine such ‘transgressive freedom’ with the agency of new media in art education. It argues that while such transgression is well aligned with the freedom of independent thinking and criticality inherent to the radicality of learning art, such freedom in learning also permits the pedagogical intrusion of new media through the utilization of technology by students in a classroom. Having this as the foundation, the paper sets out to critically examine new media as a new form of radicality—one that not only perpetuates the radicality of art by breaching the distinction between learner and teacher but also begs for a reconfiguration of the discrepancy between human and non-human in education.
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