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As engagement with art is increasingly recognized as an exciting and accepted practice in theology, theologians are faced with questions concerning the purposes of such engagement and how best to undertake it. This article argues that engagement with art is not merely the purview of an esoteric subdiscipline known as "Theology and the Arts" but offers an opportunity for theologians to confront the humanity at the heart of their own work, including guilt, error, and corruption, which will enable progress toward the goal of greater intimacy and belonging. Taking seriously the idea that both our theological concepts and our intellectual habits have been shaped by social and material realities, this article asks how we ought to think about theological engagement with art given that we are prone to colonizing habits of thought that affect such engagement. By putting theologians including Willie Jennings and Emilie Townes in conversation with theories about art from T.J. Clark, Alva Noe, and James A. Noel, we ask how theologians might resist temptations to categorize art as theology's other or absorb it into its own concerns, both of which reflect colonizing habits of mind and inure theology against a genuine confrontation with art. We recommend a posture of silence, responsive to the silence of the painting itself, in which the theologian opens to self-reflexive questions about both the operations of their own imagination, creativity, imagery, silence, and more, as well as the implications for the theological concepts used to designate those realities. [ABSTRACT FROM AUTHOR]