This chapter examines Douglass’s afterlife in art by using his theory of the image and ethics of sight to interpret contemporary visual art. While many scholars have discussed the democratic potential Douglass saw in the proliferation of inexpensive means of image capture inaugurated by the daguerreotype, less has been written on Douglass’s visual epistemology itself. This caesura leaves open questions such as how the democratic potential of pictures accords with Douglass’s contention that “pictures are decidedly conservative,” and potentially overlooks Douglass’s legacy in other mediums, including painting, drawing, sculpture, and conceptual art. In readings of work by contemporary artists Bethany Collins, Sandow Birk, and Toyin Ojih Odutola, the chapter contends that Douglass’s afterlife in art is not in the merely referential – art that either implicitly or explicitly evokes Douglass – but rather, that Douglass reflects on and prescribes a way of seeing that extends from his gaze to our own.