The hope that art could be personally or socially transformational is an important part of art history and contemporary art practice. In the twentieth century, it shaped a movement away from traditional media in an effort to make social life a medium. Artists imagined and created participatory situations designed to facilitate potentially transformative expression in those who engaged with the works. This chapter develops the concept of “transformative expression,” and illustrates how it informs a diverse range of such works. Understanding these artworks in this way raises two interesting questions, one about the nature of aesthetic value and the other about the nature of action. Answers to these questions lie in understanding the social and aesthetic character of our capacity to distance ourselves from our commitments and act in the expressive, playful, spontaneous, or imaginative ways that participatory art invites.