This volume presents a contrastive study of the overlapping careers of Shakespeare and Caravaggio through the comparison of their strikingly similar conventional belief in symbol and the centrality of the subject, only to gradually open it up in an exaltation of multiplicity and the "indistinct regard" (Othello). Utilizing a methodological premise on the notions of early modern indistinction and multiplicity, Shakespeare, Caravaggio, and the Indistinct Regard analyses the survival of English art after iconoclasm and the circulation of Italian art and motifs, methodologically reassessing the conventional comparison between painting and literature. The book examines Caravaggio's and Shakespeare's works in the perspective of the gradual waning of symbolism, the emergence of chiaroscuro and mirror imagery underneath their radically new concepts of representation, and the triumph of multiplicity and indistinction. Furthermore, this work assesses the validity of the twin concepts of multiplicity and indistinction as an interpretive tool in a dialectical interplay with much recent work on indeterminacy in literary criticism and the sciences.